Journal articles: 'Triazale'

1

Syrota, Natalia O., Sergiy V. Kemskiy, Lesya M. Saliyeva, and Mykhailo V. Vovk. "1,2,3-Triazole-4(5)-amines – Convenient Synthetic Blocks for the Construction of Triazolo-Annulated Heterocycles." Journal of Organic and Pharmaceutical Chemistry 20, no. 2 (July 20, 2022): 27–51. http://dx.doi.org/10.24959/ophcj.22.258512.

Full text

Abstract:

Aim. To analyze and summarize the synthetic potential of 1,2,3-triazole-4(5)-amines as efficient building blocks in the synthesis of triazolo-annulated pyridine, azine and azepine systems.Results and discussion. Original literature sources revealing the synthetic potential of 4(5)-amino functionalized 1,2,3-triazoles as convenient and available building blocks for the preparation of triazolo-annulated pyridines, azines and azepines were analyzed and systematized. Condensation of 1,2,3-triazole-4(5)-amines with methylene active compounds was shown to be a powerful tool for the synthesis of versatile triazolo[4,5-b]pyridines. In turn, the cyclocondensation based on 5-amino-1,2,3-triazole-4-carboxylic acids and their structurally modified derivatives was proven to be a general way for obtaining a number of triazolo[4,5-d]pyrimidine systems. Few representatives of triazolo-annulated pyridazines, 1,3-oxazines and 1,3-thiazines were synthesized by the intramolecular cyclization of the corresponding 4-aryl(carboxy-, aminomethyl)-5-amino-1,2,3-triazoles. The cyclocondensation involving 4,5-diamino-, 4-carbofunctionalized 5-amino-1,2,3-triazoles and 4-amino-5-thiocarboxamido-1,2,3-triazoles was successful for the construction of di-, oxa- and thiazepino-annulated triazoles.Conclusions. The analysis, systematization and summary of the literature regarding the synthetic potential of 1,2,3-triazole-4(5)-amines conclusively demonstrate that these structures are easily available and convenient molecular blocks for the construction of triazolo-annulated pyridine, azine and azepine systems that are important for synthetic and biomedical research.

APA, Harvard, Vancouver, ISO, and other styles

2

Pathak, Suraj Kumar, Yepeng Xiang, Manli Huang, Taian Huang, Xiaosong Cao, He Liu, Guohua Xie, and Chuluo Yang. "Fused tetracyclic tris[1,2,4]triazolo[1,3,5]triazine as a novel rigid electron acceptor for efficient thermally activated delayed fluorescence emitters." RSC Advances 10, no. 26 (2020): 15523–29. http://dx.doi.org/10.1039/d0ra01925a.

Full text

APA, Harvard, Vancouver, ISO, and other styles

3

Zeng, Qun, Yanyang Qu, Jinshan Li, and Hui Huang. "Theoretical studies on the derivatives of tris([1,2,4]triazolo)[4,3-a:4′,3′-c:4′′,3′′-e][1,3,5]triazine as high energetic compounds." RSC Advances 6, no. 7 (2016): 5419–27. http://dx.doi.org/10.1039/c5ra22524h.

Full text

APA, Harvard, Vancouver, ISO, and other styles

4

Hryhorka, H. V., М. М. Fizer, О. І. Fizer, A. O. Kryvoviaz, and M. V. Slivka. "SYNTHESIS AND CHEMICAL PROPERTIES OF 2-HEPTADECYL-[1,3]THIAZOLO[3,2-b][1,2,4]TRIAZOL-7-IUM CATION." Scientific Bulletin of the Uzhhorod University. Series «Chemistry» 48, no. 2 (May 23, 2023): 67–72. http://dx.doi.org/10.24144/2414-0260.2022.2.67-72.

Full text

Abstract:

Functional and condensed derivatives of 1,2,4-triazoles are mostly used as biologically active compounds, and modern studies increasingly report their successful use as surfactants, stabilizers for the formation of nanoparticles, components of hybrid perovskites, which are promising materials for opto-electronics. Synthesis of new [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium salts containing a long-chain heptadecyl substituent was proposed within our research. The production of the starting compounds (2-heptadecyl-4-methyl-1,2,4-triazole-3-thione and methallyl thioether of 2-heptadecyl-3-mercapto-4-methyl-1,2,4-triazole) was carried out according to a modified method annelating of the triazole ring to combined hybrid polyheterocyclic systems and a novel technique for the alkylation of symmetrical triazoles, as a result of which model compounds were obtained in high yields. The method of intramolecular electrophilic heterocyclization was used to quaternize the nitrogen atom of the triazole heterocycle. The study of the chemical properties of the obtained salt [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium was carried out on the example of anion exchange reactions, the results of which indicate the stability of the studied cation [1,3] thiazolo[3,2-b][1,2,4]triazol-7-ium upon heating in the presence of various anions. The obtained new heterocyclic salts are promising in terms of their further study as surfactants. Keywords: 1,2,4-triazole; heptadecyl; [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium salts; surfactant.

APA, Harvard, Vancouver, ISO, and other styles

5

Franco, Daiana Portella, Lucas Caruso, Nathalia Fonseca Nadur, Thiago Moreira Pereira, Renata Barbosa Lacerda, and Arthur Eugen Kümmerle. "Recent Advances in Microwave-Assisted Synthesis and Functionalization of 1,2,3- and 1,2,4-triazoles." Current Organic Chemistry 25, no. 23 (December 16, 2021): 2815–39. http://dx.doi.org/10.2174/1385272825666211011111408.

Full text

Abstract:

Triazoles are five-membered aromatic heterocyclics, which exhibit two isosteric forms (1,2,3-triazoles and 1,2,4-triazoles), as well as multiple applications in medicinal, agricultural, supramolecular, and materials sciences. Famous examples of triazoles include drugs, such as fluconazole, ribavirin, cefatrizine, and tazobactam, as well as herbicides, such as cafenstrole and metosulam. This review aims to present the recent major examples of the application of microwave-assisted organic synthesis (MAOS) to the syntheses and endfunctionalizations of 1,4- and 1,5-disubstituted 1,2,3-triazoles, 1,2,4-triazoles, 3-amino-1,2,4- triazoles, 1,2,4-triazol-3-one, and 1,2,4-triazol-3-thiol derivatives. Notably, the previous reviews on triazole syntheses have not exclusively elucidated the relevance of MAOS techniques in the obtention and derivatization of these compounds.

APA, Harvard, Vancouver, ISO, and other styles

6

Wang, Jiazhuang, Jianhua Yang, Xuxin Fu, Guiping Qin, Tiebo Xiao, and Yubo Jiang. "Synthesis of Triazole-Fused Phenanthridines through Pd-Catalyzed Intramolecular Phenyl C–H Activation of 1,5-Diaryl-1,2,3-triazoles." Synlett 30, no. 12 (June 19, 2019): 1452–56. http://dx.doi.org/10.1055/s-0037-1611859.

Full text

Abstract:

An efficient method for the synthesis of triazole-fused phenanthridines from 1,5-diaryl-1,2,3-triazoles under palladium catalysis has been developed. The reaction proceeds through Pd-catalyzed intramolecular phenyl C–H activation of 1,5-diaryl-1,2,3-triazoles. This method provides a concise and efficient pathway to construct triazolo[1,5-f]phenanthridine derivatives in excellent yields.

APA, Harvard, Vancouver, ISO, and other styles

7

Karpun, Yevhen, and Nataliia Polishchuk. "Synthesis and antimicrobial activity of s-substituted derivatives of 1,2,4-triazol-3-thiol." ScienceRise: Pharmaceutical Science, no. 3(31) (June 30, 2021): 64–69. http://dx.doi.org/10.15587/2519-4852.2021.235976.

Full text

Abstract:

The aim of the work. 1,2,4-triazole derivatives possess a wide range of pharmacological activity, so they are used for the development of drugs and active pharmaceutical ingredients. Due to the reactivity of 1,2,4-triazoles there are many options for their further structural modification on different reaction centers. Therefore, the aim of the work was to obtain new S-substituted derivatives of 1,2,4-triazole-3-thiols, study physicochemical parameters of the substances synthesized, evaluate the antimicrobial activity of new S-derivatives of the 4-R1-5-((3-(pyridin-4-yl)-1H-1,2,4-triazol-5-yl)thio)methyl)-4H-1,2,4-triazole-3-thiol series, and study some regularities of the “structure – biological activity” relationship for the synthesized compounds as well. Materials and methods. The subject of the study was new S-substituted 1,2,4-triazoles containing 2-oxopropan-1-yl and 2-aryl-2-oxoethan-1-yl substituents. The antimicrobial activity was studied by double serial dilutions on test cultures of Staphylococcus aureus (ATCC 25923), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), and Candida albicans (ATCC 885-653). The results of the biological screening showed that at a concentration of 125 g/mL, all synthesized substances showed activity (MIC – in the range of 31.25 - 62.5 μg/mL, MBCK - in the range of 62.5–125 μg/mL) against strains of Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Candida albicans. Variation of substituents on the sulfur atom did not lead to a significant change in antimicrobial and antifungal activities among derivatives of 4-R1-5-((3-(pyridin-4-yl)-1H-1,2,4-triazole-5-yl) thio)methyl)-4H-1,2,4-triazole-3-thiols. Conclusions. Biological screening data indicate the prospects for the search for new antimicrobial substances among the abovementioned derivatives of 1,2,4-triazoles. The most active compounds were 1-((4-ethyl-5-((3-(pyridin-4-yl)-1H-1,2,4-triazol-5-yl)thio)methyl)-4H-1,2,4-triazol-3-yl)thio)propan-2-one and 1-(4-methoxyphenyl)-2-(4-ethyl-5-(((3-(pyridin-4-yl)-1H)-1,2,4-triazol-5-yl)thio)methyl)-4H-1,2,4-triazol-3-yl)thio)ethanone, which showed the most pronounced antimicrobial activity against the Pseudomonas aeruginosa strain (MIC – 31.25 μg/mL, MBcK - 62.5 μg/mL)

APA, Harvard, Vancouver, ISO, and other styles

8

Fizer, O. I., M. M. Fizer, A. O. Kryvoviaz, and M. V. Slivka. "INVESTIGATION OF THE INFLUENCE OF THE SUBSTITUTE IN THE THIRD POSITION ON THE ELECTRONIC STRUCTURE OF 1,3-THIAZOLO[2,3-c][1,2,4]TRIAZOLE." Scientific Bulletin of the Uzhhorod University. Series «Chemistry» 46, no. 2 (February 10, 2022): 55–62. http://dx.doi.org/10.24144/2414-0260.2021.2.55-62.

Full text

Abstract:

Condensed 1,2,4-triazole derivatives exhibit a wide range of biological activity. In particular, triazolam, alprazolam and estazolam, which contain [1,2,4]triazolo[4,3-a][1,4]benzodiazepine system, are used as tranquilizers. Brotizolam is another tranquilizer, a derivative of thieno[3,2-f][1,2,4]triazolo [4,3-a][1,4]diazepine. The oral hypoglycemic drug sitagliptin contains the [1,2,4]triazolo[4,3-a]pyrazine system. In addition, pesticides such as flumetsulam, metosulam, cloransulam, diclosulam, florasulam, are derivatives of [1,2,4]triazolo[1,5-a]pyrimidine, [1,2,4]triazolo[1,5-c]pyrimidine and [1,2,4]triazolo[4,3-a]pyrimidine. Also, the search for anticancer drugs is based on the nucleus of 1,2,4-triazole. The popularity of the use of 1,2,4-triazole derivatives is primarily due to the high pharmacological action and relatively low toxicity of these compounds. The calculations were performed in the software package ORCA 4.2.1, by the method of density functional theory using the B3LYP/def2-TZVP method. After optimizing the geometry, to confirm the finding of the true local minimum, we calculated the matrix of the second derived energy from the coordinates of the atoms - in all cases, no imaginary frequencies were detected, indicating the finding of the true minimum. The magnetic characteristics of the compounds were calculated by the GIAO method. Using the method of density functional theory, the geometric and electronic structures of five compounds of the [1,3]thiazolo[2,3-c][1,2,4]triazole class were simulated, namely: unsubstituted [1,3]thiazolo[2,3-c][1,2,4]triazole, 3-methyl-[1,3]thiazolo[2,3-c][1,2,4]triazole, 3-ethyl-[1,3]thiazolo[2,3-c][1,2,4]triazole, 3-butyl-[1,3]thiazolo[2,3-c][1,2,4]triazole, 3-hexyl-[1,3]thiazolo[2,3-c][1,2,4]triazole. It is established that the length of the alkyl substituent in the third position has almost no effect on the shape and localization of the frontal molecular orbitals. In all cases, the isosurfaces are localized on the condensed system [1,3]thiazolo[2,3-c][1,2,4]triazole. The length of the alkyl substituent in the third position affects the ionization energy and electron affinity of [1,3]thiazolo[2,3-c][1,2,4]triazoles. Moreover, both the ionization energy and the electron affinity decrease with increasing alkyl chain length. The change in aromaticity with the change in the length of the alkyl substituent in the third position of the [1,3]thiazolo[2,3-c][1,2,4]triazole system is irregular, but the change is insignificant. It is established that both triazole and thiazole cycles are more aromatic than benzene, and the aromaticity of the triazole cycle is greater than thiazole. Keywords: 1,2,4-triazole; 1,3-thiazole, thiazolo[2,3-c][1,2,4]triazole, frontal molecular orbitals; aromaticity.

APA, Harvard, Vancouver, ISO, and other styles

9

Khomenko, Dmytro, Tetyana Shokol, Roman Doroshchuk, Ilona Raspertova, Rostyslav Lampeka, and Yulian Volovenko. "Strategies for the Synthesis of [1,2,4]Triazolo[1,5-a]pyridine-8-carbonitriles." Chemistry & Chemical Technology 17, no. 2 (June 1, 2023): 294–303. http://dx.doi.org/10.23939/chcht17.02.294.

Full text

Abstract:

Conjugated heterocyclic compounds with a 1,2,4-triazole core are of scientific interest due to their wide application in both synthetic and medicinal chemistry. In this review, we comprehensively summarize the synthetic methods for [1,2,4]triazolo[1,5-a]pyridine-8-carbonitriles. The methods are classified as follows: convertion of 8-substituted [1,2,4]triazolo[1,5-a]pyridines; synthesis based on functionalized pyridines, containing a nitrile group; synthesis based on heterocyclization of 2-(1,2,4-triazol-5-yl)acetonitriles, including cyclocondensation of 2-(1,2,4-triazol-5-yl)acetonitriles with β-dicarbonyl compounds and heterocyclization of 2-(1,2,4-triazol-5-yl)acetonitriles with α,β-unsaturated nitriles and esters; cyclocondensation of acyclic reagents, namely hydrazine derivatives and substituted methylenemalononitriles or their precursors and recyclization of oxadiazolopyridi-nium salts upon the interaction with ammonia or amine.

APA, Harvard, Vancouver, ISO, and other styles

10

Farrán, M. Ángeles, M. Ángels Bonet, Rosa M. Claramunt, M. Carmen Torralba, Ibon Alkorta, and José Elguero. "The structures of 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles related to J147, a drug for treating Alzheimer's disease." Acta Crystallographica Section C Structural Chemistry 74, no. 4 (March 28, 2018): 513–22. http://dx.doi.org/10.1107/s2053229618004394.

Full text

Abstract:

J147 [N-(2,4-dimethylphenyl)-2,2,2-trifluoro-N′-(3-methoxybenzylidene)acetohydrazide] has recently been reported as a promising new drug for the treatment of Alzheimer's disease. The X-ray structures of seven new 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles, namely 1-(3,4-dimethylphenyl)-4-phenyl-5-trifluoromethyl-1H-1,2,3-triazole (C17H14F3N3, 1), 1-(3,4-dimethylphenyl)-4-(3-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (C18H16F3N3O, 2), 1-(3,4-dimethylphenyl)-4-(4-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (C18H16F3N3O, 3), 1-(2,4-dimethylphenyl)-4-(4-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (C18H16F3N3O, 4), 1-[2,4-bis(trifluoromethyl)phenyl]-4-(3-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (C18H10F9N3O, 5), 1-(3,4-dimethoxyphenyl)-4-(3,4-dimethoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (C19H18F3N3O4, 6) and 3-[4-(3,4-dimethoxyphenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-1-yl]phenol (C17H14F3N3O3, 7), have been determined and compared to that of J147. B3LYP/6-311++G(d,p) calculations have been performed to determine the potential surface and molecular electrostatic potential (MEP) of J147, and to examine the correlation between hydrazone J147 and the 1,2,3-triazoles, both bearing a CF3 substituent. Using MEPs, it was found that the minimum-energy conformation of 4, which is nearly identical to its X-ray structure, is closely related to one of the J147 seven minima.

APA, Harvard, Vancouver, ISO, and other styles

11

Jansa, Petr, Petr Špaček, Ivan Votruba, Petra Břehová, Martin Dračínský, Blanka Klepetářová, and Zlatko Janeba. "Efficient one-pot synthesis of polysubstituted 6-[(1H-1,2,3-triazol-1-yl)methyl]uracils through the “click” protocol." Collection of Czechoslovak Chemical Communications 76, no. 9 (2011): 1121–31. http://dx.doi.org/10.1135/cccc2011074.

Full text

Abstract:

The preparation of several triazolo acyclic nucleosides and triazolo acyclic nucleoside phosphonates is described. The synthetic methodology has been developed as an efficient one-pot Cu(I)-catalyzed azide alkyne Huisgen “click” cycloaddition. A novel Cu(I)-catalyzed decarboxylation reaction of 1-substituted 1H-1,2,3-triazole-4-carboxylic acids at room temperature was observed and used for the preparation of 1-substituted 1H-1,2,3-triazoles. As congeners of TPI (Taiho pharmaceutical inhibitor), the prepared compounds were screened as potential inhibitors of human thymidine phosphorylase, but no inhibitory activity was observed.

APA, Harvard, Vancouver, ISO, and other styles

12

Rajeswar Rao, Vedula, Vedula M. Sharma, and Tadepally V. Padmanabha Rao. "Synthesis of Some New Type of Naphthothiazole Triazoles from Lawsone." Collection of Czechoslovak Chemical Communications 58, no. 5 (1993): 1191–94. http://dx.doi.org/10.1135/cccc19931191.

Full text

Abstract:

A series of 3-aryl naphto[2',3':4,5]thiazolo[3,2-b-1,2,4-triazolo-5,10-diones (V) have been prepared by the condensation of bromo lawsone (I) with 5-mercapto-3-substituted 1,2,4-triazole (II) followed by cyclization of the resulting uncyclized products (IV) with alkohol and sulfuric acid. The products are identical with the condensation products of 2,3-dichloro naphthoquinone (III) with 5-mercapto-3-substituted 1,2,4-triazoles in the presence of anhydrous alcohol containing fused sodium acetate.

APA, Harvard, Vancouver, ISO, and other styles

13

Hajri, A., D. Alimi, K. Rtibi, and H. Sebai. "Novel 6-aryl-7-alkyl/aryl-[1,2,4]triazolo[4,3-a][1,3,5]triazine-5(6H)-thiones, processes for their preparation, characterization and evaluation of their in vitro antioxidant activity." Bulletin of the Chemical Society of Ethiopia 35, no. 3 (January 31, 2022): 565–72. http://dx.doi.org/10.4314/bcse.v35i3.8.

Full text

Abstract:

ABSTRACT. A series of nine new 6-aryl-7-alkyl/aryl-[1,2,4]triazolo[4,3-a][1,3,5]triazine-5(6H)-thiones (2a-i) were synthesized by a reaction of N-triazol-3-yl imidates (1) with three different isothiocyanate derivatives (RNCS) in refluxing toluene. The structures of the final heterocyclic compounds were confirmed by 1H-NMR, 13C-NMR, FT-IR, elemental analysis, and mass spectral analysis. The target compounds (2a-i) were in vitro screened for their activity as antioxidants using DPPH (2,2′-diphenyl-1-picrylhydrazyl) and FRAP (ferric reducing/antioxidant power) methods. The results revealed that some triazolotriazine-5-(6H)thiones exhibited antioxidant activity ranging from moderate to high. The obtained findings revealed that the triazolotriazine-5-(6H)thiones (2g, 2h, and 2i) have superiority among all compounds, It is obvious that the presence of a hydroxyl group in the structure is essential for the antioxidant properties and should be taken into consideration in further design of structures with potential antioxidant properties. KEY WORDS: Imidates, Isothiocyanates, Antioxidant, Triazole, DPPH, FRAP Bull. Chem. Soc. Ethiop. 2021, 35(3), 565-572. DOI: https://dx.doi.org/10.4314/bcse.v35i3.8

APA, Harvard, Vancouver, ISO, and other styles

14

Slivka, Mikhailo, Nataliya Korol, Ivan Rusyn, and Vasyl Lendel. "Synthesis of [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium and [1,2,4]triazolo[5,1-b][1,3]thiazin-4-ium salts via regioselective electrophilic cyclization of 3-[(2-alken-1-yl)sulfanyl]-4H-1,2,4-triazoles." Heterocyclic Communications 21, no. 6 (December 1, 2015): 397–401. http://dx.doi.org/10.1515/hc-2015-0158.

Full text

Abstract:

AbstractA convenient procedure for the regioselective preparation of [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium 10 and [1,2,4]triazolo[5,1-b][1,3]thiazin-4-ium salts 9 via regioselective electrophilic cyclization of 3-[(2-alken-1-yl)sulfanyl]-4H-1,2,4-triazoles 3 is reported. Direction of electrophilic heterocyclization strongly depends on nature of the alkenyl substitutent.

APA, Harvard, Vancouver, ISO, and other styles

15

Caiana, Rodrigo Ribeiro Alves, Cosme Silva Santos, Ronaldo Nascimento de Oliveira, and Juliano Carlo Rufino Freitas. "Scientific and Technological Prospecting of 1H-1,2,3-Triazoles." Current Organic Chemistry 26, no. 3 (February 2022): 275–86. http://dx.doi.org/10.2174/1385272826666220126153429.

Full text

Abstract:

Abstract: The use of 1H-1,2,3-triazoles has become an important scaffold for applications in different technological sectors. Therefore, we sought to carry out technological monitoring to understand the international scenario involving 1H-1,2,3-triazoles from the patents filed, in addition to evaluating the relationship between the growth in the number of patents and the improvement of strategies for obtaining these compounds via a metal-catalyzed azide-alkyne cycloaddition reaction. Technological monitoring was performed with the support of the PatentInspiration ® platform, using the keywords "1,2,3-triazol", "1,2,3-triazole", and "1,2,3- triazolyl". A total of 960 registered patents were found, most for the years 2014 and 2019. The main filers were prestigious multinational companies, such as Syngenta, Merck, Sandoz, Pfizer, and Bayer. The United States, China, Japan, and Germany lead patent registrations, mainly addressing innovations in chemistry and metallurgy, human needs, and new technologies. These results help to understand the state of innovation for this topic, pointing out the characteristics of the main discoveries concerning 1H-1,2,3-triazole derivatives.

APA, Harvard, Vancouver, ISO, and other styles

16

Pandey, Vinod Kumar, Zehra Tusi, Sumerah Tusi, and Madhawanand Joshi. "Synthesis and Biological Evaluation of Some Novel 5-[(3-Aralkyl Amido/Imidoalkyl) Phenyl]-1,2,4-Triazolo[3,4-b]-1,3,4-Thiadiazines as Antiviral Agents." ISRN Organic Chemistry 2012 (September 11, 2012): 1–7. http://dx.doi.org/10.5402/2012/760517.

Full text

Abstract:

A series of novel 4-amino-5-mercapto-3-[(3-aralkyl amido/imidoalkyl) phenyl]-1,2,4-triazoles (5a-d) were obtained by treating m-(aralkyl amido/imidoalkyl) benzoic acid hydrazides (3a-d) with carbon disulphide in alcoholic KOH and hydrazine hydrate, respectively. These triazole derivatives were employed in the synthesis of 5-[(3′-aralkyl amido/imidoalkyl) phenyl]-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines (6a-d). The newly synthesized compounds were evaluated for their antiviral activity against two animal viruses, namely, Japanese encephalitis virus (JEV) strain P20778 and herpes simplex virus-1 (HSV-1) strain 753166.

APA, Harvard, Vancouver, ISO, and other styles

17

Ryzhikova, Olga V., Kseniya N. Sedenkova, Sergey V. Kositov, Victor A. Tafeenko, Yuri K. Grishin, and Elena B. Averina. "Stereoselective Approach to Hydroxyalkyl-1,2,3-triazoles Containing Cyclooctane Core and Their Use for CuAAC Catalysis." Catalysts 13, no. 5 (May 3, 2023): 835. http://dx.doi.org/10.3390/catal13050835.

Full text

Abstract:

1,2,3-Triazoles bearing additional functional groups have found applications as the ligands in catalysis of a broad scope of reactions, synthesis of transition metals complexes for various practicable purposes, and design of metal-based drugs. Triazolyl ligands accelerating CuAAC reactions, such as TBTA and TTTA, are nowadays commonly used in organic synthesis, and the search for novel ligands with a less complicated structure represents an important task. In the present work a series of hydroxyalkyltriazoles, containing a cyclooctane core, were synthesized via cycloaddition of readily available individual diastereomers of azidoalcohols or diazidodiols with phenylacetylene. The obtained hydroxyalkyltriazoles were probed as ligands for CuAAC reactions of benzyl azide with acetylenes, and 1-[(4-phenyl-1H-1,2,3-triazol-1-yl)methyl]cyclooctanol was demonstrated to act as an effective ligand for these processes. The complex salt of the abovementioned triazole and CuCl2 was readily obtained. According to X-ray diffraction analysis data, the complex contained two molecules of triazole, in which only N1-atoms of the triazole ring acted as coordination centers. Such a molecular structure correlates well with the efficiency of 1-[(4-phenyl-1H-1,2,3-triazol-1-yl)methyl]cyclooctanol as a ligand in CuAAC reactions: it is able to coordinate copper ions and, at the same time, it forms a sufficiently labile complex to not withdraw copper ions from the catalytic cycle.

APA, Harvard, Vancouver, ISO, and other styles

18

Ohloblina, M. V. "Biological features of new 1,2,4-triazole derivatives (a literature review)." Current issues in pharmacy and medicine: science and practice 15, no. 1 (February 15, 2022): 107–12. http://dx.doi.org/10.14739/2409-2932.2022.1.252305.

Full text

Abstract:

Modern chemistry of 1,2,4-triazoles is in need of the search for more rational ways of synthesizing biologically active substances. To date, a number of attractive alternatives to the classical methods for the synthesis of potentially biologically active derivatives among 1,2,4-triazoles are known. The above mentioned compounds demonstrate antimicrobial, antifungal, antioxidant, anti-inflammatory, antiviral activity, etc. Based on the results of literary sources generalization, a promising direction of scientific research was chosen. The aim of this work is to determine the direction of modern organic synthesis, clearly indicating the possibility of various chemical modeling of 1,2,4-triazoles and the peculiarities of using their derivatives. Materials and methods. The following methods were used in the work: synthetic, analytical, information retrieval, descriptive, generalization. The materials for the study comprised literary sources containing information on the relevance and prospects for further chemical modeling of 1,2,4-triazole. Results. A search, analysis and generalization of attractive alternatives to classical methods for the synthesis of potentially biologically active derivatives among 1,2,4-triazoles was carried out. Based on the study of a large amount of information and patent search over the past 10 years, about 700 sources of information have been found. They highlight the work of scientific teams from around the world devoted to screening studies of the antibacterial activity of new 3-aryl-5-mercapto-1,2,4-triazoles and tetra-O-acetyl-α-D-glucopyranosyl bromide; search for a number of new compounds among 4,5-diphenyl-4H-1,2,4-triazole-3-thiols with pronounced antibacterial activity against S. aureus and antifungal activity against Candida albicans; identification of new candidates among thiazolo[3,2-b]-1,2,4-triazol-5(6H)-one molecules with analgesic and anti-inflammatory activity; bringing moderate antimicrobial and fairly high antifungal activity of the above compounds. Conclusions. Processing, elements of systematization, comparison and generalization of modern information sources indicate rather high rates of biological activity of 1,2,4-triazole derivatives.

APA, Harvard, Vancouver, ISO, and other styles

19

Fedotov, S. O., and A. S. Hotsulia. "Synthesis and properties of 3-(ethylthio)-9-methyl-6-(alkylthio)pyrazolo[1,5-d][1,2,4]triazolo[3,4-f][1,2,4]triazines." Current issues in pharmacy and medicine: science and practice 15, no. 3 (November 15, 2022): 227–34. http://dx.doi.org/10.14739/2409-2932.2022.3.263994.

Full text

Abstract:

The combination of pyrazole and 1,2,4-triazole fragments in one structure makes it possible to achieve some success in creating potential biologically active compounds. Various factors contribute to this process. Among them, we can note the significant possibilities of chemical transformation involving these cycles, the simplicity, and reliability of methods, the creation of molecules with a certain level of bioavailability and the ability to influence a number of biochemical processes. Taking into account the presented facts, the creation of new compounds in a number of pyrazolo-triazole condensed systems is scientifically attractive with endowed features of practical significance and relevance. The aim of the work was to identify optimal conditions for the production of 3-(ethylthio)-9-methyl-6-(alkylthio)pyrazolo[1,5-d][1,2,4]triazolo[3,4-f][1,2,4]triazines and to study the properties of the target reaction products. Materials and methods. The chemical part of the work involved the step-by-step creation of target reaction products in the form of 3-(ethylthio)-9-methyl-6-(alkylthio)pyrazolo[1,5-d][1,2,4]triazolo[3,4-f][1,2,4]triazines. The first stage was aimed at conducting the interaction of diethyloxalate with acetone with the participation of sodium methylate in a methanol medium. Ethyl-2,4-dioxopentanoate was used in the conversion process to 3-methylpyrazole-5-carbohydrazide with the participation of hydrazine hydrate. Further modification of the molecule consisted of the gradual formation of the structure of 4-amino-5-(3-methylpyrazol-5-yl)-1,2,4-triazole-3-thiol. The next step involved the synthesis of 3-ethylthio-5-(3-methylpyrazol-5-yl)-1,2,4-triazole-4-amine. Further conversion included the production of potassium 3-ethylthio-9-methylpyrazolo[1,5-d][1,2,4]triazolo[3,4-f][1,2,4]triazine-6-thiolate and its S-alkyl derivatives along the triazine fragment. Cyclooxygenase-2, lanosterol-14α-demethylase and receptor tyrosine kinase were selected as model enzymes for docking, the crystal structure of which was loaded from the Protein Data Bank. Results. The synthesis of 3-(ethylthio)-9-methyl-6-(alkylthio)-pyrazolo[1,5-d][1,2,4]triazolo[3,4-f][1,2,4]triazines were carried out and the optimal conditions for the production of these substances were determined. The structure of the chemical transformation products was proved and the results of the study of the main physical properties were recorded. The results of virtual studies provided an opportunity to substantiate the prospects of the selected chemical transformation vector, which ultimately made it possible to determine the biological potential of the obtained compounds. Conclusions. Based on the results of the study, information was obtained that gives a certain idea of the possible level of influence of synthesized compounds on the activity of lanosterol-14α-demethylase, which makes it advisable to further search for substances with fungistatic and fungicidal effects.

APA, Harvard, Vancouver, ISO, and other styles

20

Rathmann, Stephanie M., Nancy Janzen, and John F. Valliant. "Synthesis, radiolabelling, and biodistribution studies of triazole derivatives for targeting melanoma." Canadian Journal of Chemistry 94, no. 9 (September 2016): 773–80. http://dx.doi.org/10.1139/cjc-2016-0239.

Full text

Abstract:

Molecular probes that target specific markers expressed in solid tumours are in demand for cancer imaging and radionuclide therapy applications. The synthesis, characterization, and in vivo evaluation of radioiodinated triazoles designed as probes to target melanoma are described here. Compounds were prepared using a thermal click reaction between ethynylstannane and methyl 2-azidoacetate, resulting in preferential formation of the corresponding 1,4-tin triazole. The primary amine of various targeting vectors was then coupled to the resulting tin triazole methyl ester. These precursors were labelled with no carrier added 123I or 125I and purified by high performance liquid chromatography to give isolated radiochemical yields between 6% and 51% and radiochemical purities of >95% in all cases. Among the evaluated compounds, N-(2-diethylamino-ethyl)-2-(4-iodo-[1,2,3]triazol-1-yl)acetamide (7a) and N-(1-benzylpiperidin-4-yl)-2-(4-iodo-1H-1,2,3-triazol-1-yl)acetamide (7d) showed the most promising in vivo data, and their 123I-labelled forms were used in single photon emission computed tomography computed tomography (SPECT–CT) imaging studies. The imaging data showed excellent tumour visualization with a very high signal to noise ratio.

APA, Harvard, Vancouver, ISO, and other styles

21

Gotsulya, A. S., A. I. Panasenko, E. G. Knysh, and A. O. Pryimenko. "UV-spectrophotometric study of the 7-((3-thio-4-R-1,2,4-triazole-3-yl)methyl)-theophyllines." Farmatsevtychnyi zhurnal, no. 4 (September 4, 2018): 65–70. http://dx.doi.org/10.32352/0367-3057.4.15.03.

Full text

Abstract:

Chemistry of the 1,2,4-triazole derivatives recently attracts the attention of many scientists, mainly due to the presence of the number of the valuable pharmacological properties. In modern medical practice, there are many examples of successful heterocyclic systems derivatives usage. First of all, it is a group of drugs with antifungal activity (fluconazole, itraconazole, voriconazole, pozakonazol), antidepressant activity (alprazolam, triazolam), anticancer activity (anastrozole, letrozole). But despite the great practical importance of works in this area, the structure of 1,2,4-triazoles-3-thione derivatives have been studied imperfectly. Therefore, the study of this class of compounds is actual now. The aim of this work was to study the UV-spectra of the research compounds in different polarity solvents (water, 95% ethanol, 0,1 M and 1 M sodium hydroxide, 0,1 M and 1 M hydrochloric acid, 0,1 M and 1 M sulfate acid solution, chloroform, isopropanol, acetonitrile and dioxane) for structure–spectral data relationship establishing. Spectrophotometer SPECORD 200-222U214 was used to study the UV-spectra of the analyzed compounds and to measure their intensity. During the research, it was found that the electronic spectra of 7-((3-thio-4-methyl-1,2,4-triazoles-5-yl)methyl)theophylline, 7-((3-thio-4-ethyl-1,2,4-triazolе-5-yl)methyl)theophylline and 7-((3-thio-4-phenyl-1,2,4-triazolе-5-yl)methyl)-theophylline were characterized by maximums in the short-wave (203–235 nm) and medium-wavе part (250–272 nm) of UV-spectrum. Due to the presence of the methylene fragment in investigated molecules, which connects the purine cycle with 1,2,4-triazole, absorbtion maximums were caused by π→π*-electron jumping of the corresponding type 1La and 1Lb.

APA, Harvard, Vancouver, ISO, and other styles

22

Sonawane, R., and M. A. Sagare. "Design, Synthesis and Evaluation of Some Substituted Triazole Phenyl Methanones from Substituted Anilines." Asian Journal of Organic & Medicinal Chemistry 7, no. 4 (2023): 295–98. http://dx.doi.org/10.14233/ajomc.2022.ajomc-p405.

Full text

Abstract:

Triazoles, a five-membered ring structure and three nitrogen atoms, are regarded as important building blocks for the synthesis of numerous organic compounds. Triazoles and their derivatives have received considerable attention over the past decade due to their chemotherapeutic value. It’s been thought to be a functional core that exhibits most varieties of biological activity mainly antibiotics, antimicrobials and antifungals. In present work, a series of novel substituted triazole phenylmethanones were synthesized using Claisen-Schmidt condensation reaction of 1-(5-methyl-1-(substituted phenyl)-1H- 1,2,3-triazol-4-yl)-ethan-1-one (3a-d) and some aromatic aldehydes. Final compounds (5a-f) were synthesized from compounds 4a-d, hydrazine hydrate and benzoic acid by sequential reactions having intermolecular conjugate addition and formation of hydrazone. All the intermediate and final compounds were characterized from the mass, elemental and 1H NMR spectral data.

APA, Harvard, Vancouver, ISO, and other styles

23

Bortolot, Carolina S., Luana da S.M. Forezi, Roberta K. F. Marra, Marcelo I. P. Reis, Bárbara V. F. e. Sá, Ricardo I. Filho, Zeinab Ghasemishahrestani, et al. "Design, Synthesis and Biological Evaluation of 1H-1,2,3-Triazole-Linked-1H-Dibenzo[b,h]xanthenes as Inductors of ROS-Mediated Apoptosis in the Breast Cancer Cell Line MCF-7." Medicinal Chemistry 15, no. 2 (February 12, 2019): 119–29. http://dx.doi.org/10.2174/1573406414666180524071409.

Full text

Abstract:

Background:Low molecular weight 1,2,3-triazoles and naphthoquinones are endowed with various types of biological activity, such as against cancer, HIV and bacteria. However, in some cases, the conjugation of these two nuclei considerably increases their biological activities.Objective:In this work, we decided to study the synthesis and screening of bis-naphthoquinones and xanthenes tethered to 1,2,3-triazoles against cancer cell lines, specifically the human breast cancer cell line MCF-7.Results:Starting from lawsone and aryl-1H-1,2,3-triazole-4-carbaldehydes (10a-h) several new 7- (1-aryl-1H-1,2,3-triazol-4-yl)-6H-dibenzo[b,h]xanthene-5,6,8,13(7H)-tetraones (12a-h) and 3,3'- ((1-aryl-1H-1,2,3-triazol-4-yl)methylene)bis(2-hydroxynaphthalene-1,4-diones) 11a-h were synthesized and evaluated for their cytotoxic activities using the human breast cancer cell line MCF-7 and the non-tumor cell line MCF10A as control. We performed test of cell viability, cell proliferation, intracellular ATP content and cell cytometry to determine reactive oxygen species (ROS) formation.Conclusions:Based on these results, we found that compound 12a promotes ROS production, interfering with energy metabolism, cell viability and proliferation, and thus promoting whole cell damage.

APA, Harvard, Vancouver, ISO, and other styles

24

Joshi, K. A., J. M. Dhalani, H. B. Bhatt, and K. M. Kapadiya. "Synthesis of some new 6-aryl-3-(4-isopropylphenyl)[1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles and its anti-microbial study." Current Chemistry Letters 10, no. 4 (2021): 479–88. http://dx.doi.org/10.5267/j.ccl.2021.4.003.

Full text

Abstract:

New series of fused 1,2,4-triazoles, i.e., 3-(4-isopropylphenyl)-6-substituted phenyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles (5a-5j) have been synthesized via a four-step procedure and using eco-friendly reaction condition at some steps of the synthesis. It was adopted by the formation of hydrazide of methyl 4-isopropylbenzoate (1) followed by reaction with CS2 in basic media to afford potassium salt, which on cyclized to our essential step, 4-amino-5-(4-isopropylphenyl)-4H-1,2,4-triazole-3-thiol (4). The desired adducts (5a-5j) were formed by (4) on reaction with various aromatic acids in POCl3 media. The newly synthesized triazolo- thiadiazoles have been characterized by different spectroscopic techniques and investigated for their in vitro antibacterial and antifungal activity. It was revealed that the compounds 5a, 5c, 5h, and 5i showed interesting antibacterial and antifungal activity compared to the used reference standard.

APA, Harvard, Vancouver, ISO, and other styles

25

Canseco-González, Daniel, José Luis Rodríguez de la O, and José Enrique Herbert-Pucheta. "Combined XRD-paramagnetic 13C NMR spectroscopy of 1,2,3-triazoles for revealing copper traces in a Huisgen click-chemistry cycloaddition. A model case." Heterocyclic Communications 25, no. 1 (November 28, 2019): 98–106. http://dx.doi.org/10.1515/hc-2019-0018.

Full text

Abstract:

AbstractCopper-catalyzed Alkyne-Azide Cycloaddition (CuAAC) click chemistry robustness has been demonstrated over recent years to produce 1,2,3-triazoles with excellent yields at mild conditions with simple purification methods. However, the consequences of having copper paramagnetic traces in final products, which complicate spectroscopic assignments and can produce inaccurate conclusions, has been scarcely discussed. Herein we present a strategy that combines X-Ray Diffraction (XRD) with 13C- paramagnetic Nuclear Magnetic Resonance spectroscopy, in order to demonstrate the presence of paramagnetic metal traces at standard Huisgen synthesis and purification conditions. We also demonstrate that the derivatization of 1,4-disubstituted-1,2,3-triazoles to produce 1,3,4,-trisubstituted-1,2,3.triazolium salts, promotes an efficient removal of Cu(II/I) moieties. Evidence of paramagnetic metal moieties is given using XRD structural analysis of abnormalities in torsional angles between substituents and the 1,2,3-triazole center, in parallel to 13C- paramagnetic NMR chemical shift and line width analysis. As model systems to demonstrate the importance of characterizing paramagnetic traces, we present the synthesis of novel 1-((3s,5s,7s)-adamantan-1-yl)-4-cyclopropyl-1H-1,2,3-triazole and its derivatized 1-((3s,5s,7s)-adamantan-1-yl)-4-cyclopropyl-3-methyl-1H-[1,2,3]-triazol-3-ium triflate salt.

APA, Harvard, Vancouver, ISO, and other styles

26

Kar, C., and K. Gupta. "Effect of triazole-type plant growth regulators on sunflower and safflower seed viability." Canadian Journal of Botany 69, no. 6 (June 1, 1991): 1344–48. http://dx.doi.org/10.1139/b91-174.

Full text

Abstract:

Pretreatment of sunflower and safflower seeds with triazole-type plant growth regulators (triazoles) diminished the rate of germination and reduced seedling growth. However, if seeds were aged at 90% relative humidity (accelerated ageing), triazoles significantly reduced the deleterious effects of accelerated ageing on germination percentage and field emergence. Seedling vigour was also greater in seedlings raised from triazole-treated seeds than from untreated seeds after accelerated aging. The activities of enzymes like dehydrogenase declined at a faster rate during accelerated ageing in untreated control than in triazole-treated seeds. Triazoles also slowed down the degradation of ribonucleic acid. The rate of change of soluble carbohydrates and amino acids was low in triazole-treated seeds compared with untreated control seeds. A positive correlation was evident between increase in membrane permeability and loss of seed viability. Membrane permeability and level of malondialdehyde, a peroxidation product of unsaturated fatty acids, gradually increased in storage at 90% relative humidity, but in seeds pretreated with triazoles these changes were minimal. Key words: triazoles, accelerated ageing, sunflower and safflower seed viability.

APA, Harvard, Vancouver, ISO, and other styles

27

Ravikumar, Krishnan, Balasubramanian Sridhar, Jagadeesh Babu Nanubolu, Venkatasubramanian Hariharakrishnan, and Awadesh Narain Singh. "Structures of benzoxazine-fused triazoles as potential diuretic agents." Acta Crystallographica Section C Crystal Structure Communications 68, no. 8 (July 13, 2012): o302—o307. http://dx.doi.org/10.1107/s0108270112029800.

Full text

Abstract:

6,8-Dinitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one, C9H5N5O6, (I), a potential diuretic, and its acetylacetone derivative (E)-2-(2-hydroxy-4-oxopent-2-en-3-yl)-6,8-dinitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one, C14H11N5O8, (II), both crystallize from methanol but in centrosymmetric and noncentrosymmetric space groups, respectively. To the best of our knowledge, this is the first report of crystal structures of benzoxazine–triazole fused systems. The acetylacetone group in (II) exists as the keto–enol tautomer and is oriented perpendicular to the triazol-3-one ring. Of the two nitro groups present, one is rotated significantly less than the other in both structures. The oxazine ring adopts a screw-boat conformation in (II), whereas it is almost planar in (I). N—H...N and N—H...O hydrogen bonds form centrosymmetric dimers in (I), while C—H...O interactions associate the molecules into helical columns in (II).

APA, Harvard, Vancouver, ISO, and other styles

28

Singh, Rakesh, Harpreet Kaur, and Pankaj Gupta. "1,2,3-Triazoles: Lead Molecules For Promising Drugs: A Review." Asian Journal of Chemistry 33, no. 12 (2021): 2896–918. http://dx.doi.org/10.14233/ajchem.2021.23488.

Full text

Abstract:

A large number of heterocyclic compounds with five membered rings as the parent nucleus such as tetrazoles, imidazoles, triazoles, oxadiazoles, thiadiazoles, thiazoles, etc. have been studied extensively owing to their fascinating biological properties like anticancer, antifungal, antimicrobial, antitumor, anticonvulsant, antiviral, etc. 1,2,3-Triazoles are important class of five-membered biologically active heterocyclic compounds as they exhibit wide range of pharmacological activities. Triazoles are of two types viz. 1,2,3-triazole and 1,2,4-triazole. These compounds have drawn great attention from chemists and biologists since their discovery. In recent years, triazoles has emerged as an interesting field in drug design for many researchers due to their enormous pharmacological scope. The present review aims to sum up the medicinal significance of 1,2,3-triazoles as one of the most significant structures for the development of drug molecules like anticancer, antibacterial, HIV protease inhibitors, antifungal, anti-inflammatory (COX-1/COX-2 inhibitors), antiprotozoal, anticonvulsant, antioxidant and others, which are under clinical trials. Various benzyl and benzyl-halide functionalized 1,2,3-triazole derivatives like rufinamide, mubritinib (TAK-165) and suvorexant showing excellent biological activities have been used as medicine. In present review, more stress has been laid on the major developments in the therapeutic aspects of triazole pharmacophore for the last two decades.

APA, Harvard, Vancouver, ISO, and other styles

29

Kantlehner, Willi, Kai Edelmann, and Wolfgang Frey. "Orthoamide und Iminiumsalze, LXXXII [1]. Die Spaltung von Alkincarbonsäure-orthoamiden mit Trimethylsilylazid / Orthoamides and Iminium Salts LXXXII [1]. The Cleavage of Orthoamides of Alkynecarboxylic Acids by Trimethylsilyl Azide." Zeitschrift für Naturforschung B 67, no. 9 (September 1, 2012): 913–20. http://dx.doi.org/10.5560/znb.2012-0124.

Full text

Abstract:

The cleavage of orthoamides of alkynecarboxylic acids 5 with trimethylsilyl azide affords 4-[bis(dimethylamino)methylene]-4H-1,2,3-triazoles 9. By treatment of the bis-orthoamide of acetylenedicarboxylic acid 1 with trimethylsilyl azide and benzoyl azide, respectively, the 5- [bis(dimethylamino)methylene]-5H-1,2,3-triazole carboxamidinium salt 12a is accessible. Iminium salts 10 and 14 can be prepared by methylation of the triazoles 9 and 12a in 2-position of the triazole ring. The crystal structure of 5H-1,2,3-triazole-4-carboxamidinium tetraphenylborate 12b is reported

APA, Harvard, Vancouver, ISO, and other styles

30

Jalihal, Prabhu C., Vaibhav Rajoriya, and Varsha Kashaw. "DESIGN, SYNTHESIS, AND EVALUATION OF NEW DERIVATIVE OF 1,2,4-TRIAZOLES FOR ANTIMICROBIAL AND ANTI-INFLAMMATORY ACTIVITY." International Journal of Current Pharmaceutical Research 10, no. 4 (July 16, 2018): 29. http://dx.doi.org/10.22159/ijcpr.2018v10i4.28455.

Full text

Abstract:

Objective: The object of the study is to design, synthesize and biological evaluation of isoniazid derived 1,2,4-triazoles compounds.Methods: Isoniazid based 1,2,4-triazoles derivatives have been synthesized by reaction of Isoniazid with carbon disulfide in basic medium (KOH) to form Potassium dithiocarbazinate salt and reaction with hydrazine hydrate converted into 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol. These compounds were reacted with seven different benzaldehyde to form 4-[(substituted phenyl)-methylene]-amino-5-(pyridine-4-yl)-4H-1,2,4-triazol-3-thiol (4). The final compounds were synthesized by reaction with four different acetanilide to form 4-[substituted phenyl)-methylene]-amino-3-(N-substitutedcarboxamidomethylthio)-5-(pyridine-4-yl)-4H-1,2,4-triazoles derivatives. All these compounds were characterized by IR, 1H-NMR, [13]C-NMR and elemental analysis. The antimicrobial activity was determined by the cup plate method. Acute anti-inflammatory activity determined by using carrageenan-induced rat paw edema model.Results: Series PJ-A4, PJ-A7 and PJ-A13 showed more than 90% of the zone of inhibition against both Gram positive and Gram negative organisms. The antifungal study suggested that among synthesized compounds series PJ-A4, A7, A9, A11 and A13 showed more than 90% of zone of inhibition, A2, A10 and A12 shows more than 80% of the zone of inhibition. Anti-inflammatory study data indicate that compounds PJ-A4, PJ-A8, PJ-A9 and PJ-A13 produced 70 to 76% of paw edema inhibition compare to standard drug Ibuprofen which showed 83.3% after 5 h. Conclusion: Results suggested that the isoniazid based 1,2,4-triazole derivatives have significant antibacterial, antifungal and anti-inflammatory activity.

APA, Harvard, Vancouver, ISO, and other styles

31

Tang, Yongxing, Ziwei An, Ajay Kumar Chinnam, Richard J. Staples, and Jean'ne M. Shreeve. "Very thermostable energetic materials based on a fused-triazole: 3,6-diamino-1H-[1,2,4]triazolo[4,3-b][1,2,4]triazole." New Journal of Chemistry 45, no. 1 (2021): 85–91. http://dx.doi.org/10.1039/d0nj05152g.

Full text

APA, Harvard, Vancouver, ISO, and other styles

32

Khan, Imtiaz, Shahid Hameed, Najim A. Al-Masoudi, Nabeel A. Abdul-Reda, and Jim Simpson. "New triazolothiadiazole and triazolothiadiazine derivatives as kinesin Eg5 and HIV inhibitors: synthesis, QSAR and modeling studies." Zeitschrift für Naturforschung B 70, no. 1 (January 1, 2015): 47–58. http://dx.doi.org/10.1515/znb-2014-0162.

Full text

Abstract:

AbstractA new series of fused 1,2,4-triazoles, namely 6-aryl-3-(furan-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles 3a–h and 4a–f as well as 6-aryl-3-(furan-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines 5a–h, were synthesized by the condensation of 4-amino-5-(furan-2-yl)-4H-1,2,4-triazole-3-thiol (2) with substituted aromatic acids and phenacyl bromides, respectively. The structures of the newly synthesized compounds were established using spectroscopic analysis, while that of 3e was confirmed independently by a single-crystal X-ray structure determination. The compounds were evaluated for their antiviral activity against the replication of HIV-1 and HIV-2 in MT-4 cells using an MTT assay. In a docking study, 4b interacted with several amino acids in the reverse transcriptase (RT) binding site of HIV-1. Some new analogues were selected for evaluation of their Eg5 inhibitory activity using an in vitro malachite green ATPase assay. The QSAR of these new analogues was studied as well.

APA, Harvard, Vancouver, ISO, and other styles

33

Maj, Anna, Agnieszka Kudelko, and Marcin Świątkowski. "Novel Conjugated s-Tetrazine Derivatives Bearing a 4H-1,2,4-Triazole Scaffold: Synthesis and Luminescent Properties." Molecules 27, no. 2 (January 11, 2022): 459. http://dx.doi.org/10.3390/molecules27020459.

Full text

Abstract:

A series of new symmetrical s-tetrazine derivatives, coupled via a 1,4-phenylene linkage with a 4H-1,2,4-triazole ring, were obtained. The combination of these two rings in an extensively coupled system has significant potential applications, mainly in optoelectronics. The methodology used turned out to be useful regardless of the type of five-membered ring or the nature of the individual substituents. All the products were identified by spectroscopic methods, and the target compounds were tested for luminescent properties. This study showed that all the synthesized highly-conjugated triazoles exhibited luminescence; in particular, one derivative, 3,6-bis(4-(5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazol-3-yl)phenyl)-1,2,4,5-tetrazine (13b), showed strong fluorescence emission and ahigh quantum yield close to 1.

APA, Harvard, Vancouver, ISO, and other styles

34

Cebeci, Yıldız Uygun, and Şengül Alpay Karaoğlu. "Design and microwave-assisted synthesis of a novel Mannich base and conazole derivatives and their biological assessment." Heterocyclic Communications 27, no. 1 (January 1, 2021): 100–111. http://dx.doi.org/10.1515/hc-2020-0126.

Full text

Abstract:

Abstract 4-Amino-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (1) was converted to the corresponding Schiff base (2) by treatment with salicylaldehyde. 1,2,4-Triazoles were then converted to the corresponding Mannich bases containing fluroquinolone core using a one-pot three-component procedure. Moreover, the synthesis of six compounds, which can be considered as conazole analogues, was performed starting from 1,2,4-triazole-3-one compounds via three steps by either conventional or microwave-mediated conditions. All the newly synthesized compounds were screened for their antimicrobial activities. Most exhibited good to moderate antibacterial and/or antifungal activity. The structural assignments of the new compounds were based on elemental analysis and spectral (IR, 1H NMR, 13C NMR, and LC-MS) data.

APA, Harvard, Vancouver, ISO, and other styles

35

Palchak, Zachary L., Paula T. Nguyen, and Catharine H. Larsen. "Synthesis of alpha-tetrasubstituted triazoles by copper-catalyzed silyl deprotection/azide cycloaddition." Beilstein Journal of Organic Chemistry 11 (August 14, 2015): 1425–33. http://dx.doi.org/10.3762/bjoc.11.154.

Full text

Abstract:

Propargylamines are popular substrates for triazole formation, but tetrasubstituted variants have required multistep syntheses involving stoichiometric amounts of metal. A recent cyclohexanone–amine–silylacetylene coupling forms silyl-protected tetrasubstituted propargylamines in a single copper-catalyzed step. The development of the tandem silyl deprotection–triazole formation reported herein offers rapid access to alpha-tetrasubstituted triazoles. A streamlined two-step approach to this uncommon class of hindered triazoles will accelerate exploration of their therapeutic potential. The superior activity of copper(II) triflate in the formation of triazoles from sensitive alkyne substrates extends to simple terminal alkynes.

APA, Harvard, Vancouver, ISO, and other styles

36

Бакумовська, Х. Д., and А. С. Гоцуля. "Synthesis and properties of 7-((6-aryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl)methyl)theophyllines." Farmatsevtychnyi zhurnal, no. 1 (February 27, 2023): 58–65. http://dx.doi.org/10.32352/0367-3057.1.23.06.

Full text

Abstract:

The creation of new biologically active compounds is a promising area of modern medicinal chemistry. Heterocyclic systems play an important role in this process.Among them, it is necessary to note 1,2,4-triazole and xanthine, the presence of which in the structure of known medicines determines their pharmacological activity. The combination of these heterocycles within a single molecule can lead to the enhancement of the existing biological effect or the emergence of new useful properties. The aim of the work has been to synthesize new theophylline-containing 4-amino-1,2,4-triazole-3-thiol derivatives, study their physicochemical properties and predictive study of their biological potential. The research objects have been the 7-((6-aryl-[1,2,4]triazolo[3,4-b][1,3,4]-thiadiazol-3-yl)methyl)theophylline, which were obtained by condensation of the starting 7-((4-amino-5-mercapto-1,2,4-triazol-3-yl)methyl)theophylline with aromatic carboxylic acids (benzoic,2-methoxybenzoic, 3-methoxybenzoic, 2-bromo-5-methoxybenzoic,2-bromo-4-fluorobenzoic, 2-chloro-4-nitrobenzoic, 2-bromo-5-nitrobenzoic) in phosphorus oxychloride medium under heating. The structure of the intermediate 7-((4-amino-5-mercapto-1,2,4-triazol-3-yl)methyl)theophylline was formed by a multistep chemical transformation of 1,3-dimethylxanthine. The structure of the synthesized compounds has been confirmed by elemental analysis, 1H NMR and IR spectroscopy, their individuality has been established by chromatography-mass spectrometry. The feasibility of further biological research has been preliminarily assessed by an in silico method, in particular, molecular docking. Cyclooxygenase-2, lanosterol 14α-demethylase and anaplastic lymphoma kinase have been used as model enzymes. The most likely activity, which is quite probable in a number of synthesized compounds, is antifungal. In this context, 7-((6-(2-bromo-5-methoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl)methyl)theophylline looks particularly promising, as it exceeds ketoconazole in terms of the energy of intermolecular interactions with lanosterol 14α-demethylase.

APA, Harvard, Vancouver, ISO, and other styles

37

Shah, Tariq A., Zubair Ahmad, Niyaz A. Mir, M. Muneer, Nigam P. Rath, and Musheer Ahmad. "One step synthesis of highly functionalized thiazolo[3,2-b][1,2,4]triazole, triazolo[1,5-a]pyrimidine and triazolo[3,4-b][1,3,4]thiadiazine." RSC Advances 5, no. 130 (2015): 107931–37. http://dx.doi.org/10.1039/c5ra21270g.

Full text

APA, Harvard, Vancouver, ISO, and other styles

38

Cools, H. J., B. A. Fraaije, S. H. Kim, and J. A. Lucas. "Impact of changes in the target P450 CYP51 enzyme associated with altered triazole-sensitivity in fungal pathogens of cereal crops." Biochemical Society Transactions 34, no. 6 (October 25, 2006): 1219–22. http://dx.doi.org/10.1042/bst0341219.

Full text

Abstract:

Control of diseases caused by fungi in both medicine and agriculture is heavily dependent on the use of triazoles. As a consequence, resistance to triazoles is a threat to both human health and the sustainability of agricultural production systems. In human pathogens, particularly Candida albicans, mutations encoding alterations in the target cytochrome P450 sterol 14α-demethylase (CYP51; where CYP is cytochrome P450) enzyme are the primary determinants of triazole resistance. In fungal pathogens of cereals, CYP51A1 modifications, some at positions known to contribute to a resistant phenotype in human pathogens, have also been identified in isolates with altered triazole-sensitivity. However, unlike medicine where resistance to triazoles is a major clinical problem, failures of triazoles to control crop diseases in the field are rare with mean population sensitivities generally remaining low, perhaps due to differences in the selection pressures imposed on human and cereal pathogen populations. Nonetheless, the biological potential for resistance exists, and the question remains as to whether widespread triazole resistance can develop in an important cereal pathogen.

APA, Harvard, Vancouver, ISO, and other styles

39

Danilkina, Natalia A., Nina S. Bukhtiiarova, Anastasia I. Govdi, Anna A. Vasileva, Andrey M. Rumyantsev, Artemii A. Volkov, Nikita I. Sharaev, et al. "Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines." Molecules 24, no. 13 (June 27, 2019): 2386. http://dx.doi.org/10.3390/molecules24132386.

Full text

Abstract:

An efficient approach towards the synthesis of 6-aryl-4-azidocinnolines was developed with the aim of exploring the photophysical properties of 6-aryl-4-azidocinnolines and their click reaction products with alkynes, 6-aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines. The synthetic route is based on the Richter-type cyclization of 2-ethynyl-4-aryltriazenes with the formation of 4-bromo-6-arylcinnolines and nucleophilic substitution of a bromine atom with an azide functional group. The developed synthetic approach is tolerant to variations of functional groups on the aryl moiety. The resulting azidocinnolines were found to be reactive in both CuAAC with terminal alkynes and SPAAC with diazacyclononyne, yielding 4-triazolylcinnolines. It was found that 4-azido-6-arylcinnolines possess weak fluorescent properties, while conversion of the azido function into a triazole ring led to complete fluorescence quenching. The lack of fluorescence in triazoles could be explained by the non-planar structure of triazolylcinnolines and a possible photoinduced electron transfer (PET) mechanism. Among the series of 4-triazolylcinnoline derivatives a compound bearing hydroxyalkyl substituent at triazole ring was found to be cytotoxic to HeLa cells.

APA, Harvard, Vancouver, ISO, and other styles

40

Neelgundmath, Mahabaleshwaraiah, and Oblennavar Kotresh. "Synthesis, Evaluation and Characterization of Some 1,3,4-Triazole-2-one Derivatives as Antimicrobial Agents." E-Journal of Chemistry 9, no. 4 (2012): 2407–14. http://dx.doi.org/10.1155/2012/672125.

Full text

Abstract:

A series of novel compounds like 3[(phenyl substituted)-5-methyl-1(Benzosulphonylamine)]-1,3,4-triazole-2-ones II(a-f) were synthesized by treating 4-amino-1-phenyl-3-methyl-5-oxo-1,2,4-triazoles with benzene sulphonyl chloride using pyridine as solvent. Similarly by using 4-amino-1-aryl-3-methyl-5-oxo-1,2,4-triazoles and acetic anhydride as starting material 3[(phenyl substituted)-5-methyl-1(acetylamino)]-1,3,4-triazole-2-ones III(a-f) were synthesized and also 3[(phenyl substituted)-5-methyl-1(chloroacetyl)]-1,3,4-triazole-2-ones I(a-f) were synthesized by treating 4-amino-1-aryl-3-methyl-5-oxo-1,2,4-triazoles with chloroacetyl chloride in presence of a non-polar solvent like benzene. Elemental analysis, GCMS, IR, and1H NMR confirmed the structures of the newly synthesised compounds. The newly synthesized compounds are also screened for their antibacterial, antifungal and anti-inflammatory activities.

APA, Harvard, Vancouver, ISO, and other styles

41

Ali, Abdelselam S., John S. Wilkie, and Kevin N. Winzenberg. "Synthesis of Some 1H-1,2,4-Triazole, 4H-1,2,4-Triazole, Thiazolo[2,3-c]-1,2,4-triazole and 5H-1,2,4-Triazolo-[3,4-b][1,3]thiazine Derivatives by Metal Compound-Mediated Oxidative Cyclization of Derivatives of 2-(Phenylmethylidene)hydrazinecarboximidothioic Acid." Australian Journal of Chemistry 50, no. 9 (1997): 911. http://dx.doi.org/10.1071/c97058.

Full text

Abstract:

Reaction of the methyl 2-(phenylmethylidene)hydrazinecarboximidothioate derivatives (3a–d) and (6a,b) with iron(III) chloride afforded the 5-methylsulfanyl-3-phenyl-4H-1,2,4-triazole derivatives (4a–d) and the 5-methylsulfanyl-3-phenyl-1H-1,2,4-triazole derivatives (7a,b). This reaction was extended to the synthesis of the 3-phenyl-5,6-dihydrothiazolo[2,3-c]-1,2,4-triazole derivatives (10a,b) and the 3-phenyl-6,7-dihydro-5H-1,2,4-triazolo[3,4-b][1,3]thiazine derivatives (10c,d). Reaction of 5-(3-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (12a) with 1,2-dibromoethane gave (10a) together with the isomeric 2-(3-chlorophenyl)-5,6-dihydrothiazolo[3,2-b][1,2,4]triazole (13a); similarly, reaction of (12a) with 1,3-dibromopropane afforded (10c) along with 2-(3-chlorophenyl)-6,7-dihydro-5H-[1,2,4]triazolo[5,1-b][1,3]thiazine (13b). The use of nickel peroxide and lead tetraacetate in place of iron(III) chloride was investigated for some of these oxidative cyclization reactions.

APA, Harvard, Vancouver, ISO, and other styles

42

Mroczyńska, Martyna, Ewelina Kurzyk, Magdalena Śliwka-Kaszyńska, Urszula Nawrot, Marta Adamik, and Anna Brillowska-Dąbrowska. "The Effect of Posaconazole, Itraconazole and Voriconazole in the Culture Medium on Aspergillus fumigatus Triazole Resistance." Microorganisms 8, no. 2 (February 19, 2020): 285. http://dx.doi.org/10.3390/microorganisms8020285.

Full text

Abstract:

Triazoles are the only compounds used as antibiotics in both medicine and agriculture. The presence of triazoles in the environment can contribute to the acquisition of azole resistance among isolates of Aspergillus fumigatus. The objective of this study was to investigate the effect of A. fumigatus exposure to triazoles on susceptibility to these compounds. Seventeen triazole-resistant and 21 triazole-sensitive A. fumigatus isolates were examined. The isolates were transferred 20 times on the Sabouraud medium supplemented with posaconazole, itraconazole or voriconazole, followed by five times on the medium not supplemented. The minimum inhibitory concentrations of antimycotics were examined according to the EUCAST broth microdilution method after the 20th transfer and also the 25th transfer. In addition, the expression levels of genes mdr1, mdr2, mdr3, atrF, cyp51A and cyp51B were determined. Cultivation of A. fumigatus on media supplemented with posaconazole, itraconazole and voriconazole resulted in the acquisition of resistance to the tested triazoles of all examined isolates. After recultivation on Sabouraud without azoles, most of the isolates lost their acquired resistance. The long-term use of triazole compounds in agriculture may result in the occurrence of triazole resistant A. fumigatus isolates in the environment, not only by induction or selection of mutations in the cyp51A gene, but also by contribution to changes in the gene expression.

APA, Harvard, Vancouver, ISO, and other styles

43

Safonov, A. A., and O. I. Panasenko. "Synthesis, antimicrobial and antifungal activity of 3-(2-bromophenyl)-5-(alkylthio)-4-phenyl-4H-1,2,4-triazoles." Current issues in pharmacy and medicine: science and practice 15, no. 3 (November 15, 2022): 235–40. http://dx.doi.org/10.14739/2409-2932.2022.3.264691.

Full text

Abstract:

To select a molecule that could become a promising pharmacological agent, chemists use already-known heterocyclic bases by adding pharmacologically active groups. One such heterocyclic system is 1,2,4-triazole base, on the basis of which a huge number of biologically active compounds have already been found. It is known that 1,2,4-triazole derivatives show a fairly high antimicrobial and antifungal effect while remaining low-toxic compounds and 5-alkylthio-1,2,4-triazoles exhibit antimicrobial and antifungal activity. Based on the literature search, it can be concluded that 3-(2-bromophenyl)-5-(alkylthio)-4-phenyl-4H-1,2,4-triazoles are insufficiently studied. The aim of the work was to synthesize and investigate antimicrobial and antifungal activity among 3-(2-bromophenyl)-5-(alkylthio)-4-phenyl-4H-1,2,4-triazoles. Materials and methods. It was used 5-(2-bromophenyl)-4-phenyl-4H-1,2,4-triazole-3-thiol as a starting substance, which was synthesized by previously described techniques. 3-(2-Bromophenyl)-5-(alkylthio)-4-phenyl-4H-1,2,4-triazoles were obtained by alkylation of the starting thiol with halohenalkanes (according to the first method) and the addition of hydrochloric acid in an alcoholic medium, then subsequent heating in microwave synthesis system (by the second method). To study the antimicrobial and antifungal activity of the newly synthesized 3-(2-bromophenyl)-5-(alkylthio)-4-phenyl-4H-1,2,4-triazoles, the method of serial dilutions was used according to guidelines. Results. 3-(2-Bromophenyl)-5-(alkylthio)-4-phenyl-4H-1,2,4-triazoles were obtained by two methods: a) an equivalent amount of halohenalkane was added to 5-(2-bromophenyl)-4-phenyl-4H-1,2,4-triazole-3-thiol (I) (solvent – KOH pre-dissolved in 2-propanol). Boiled to pH = 7; b) 5-(2-bromophenyl)-4-phenyl-4H-1,2,4-triazole-3-thiol (I) (solvent – methyl or 1-propyl alcohol and 10 drops of HCl) was heated in Milestone Flexi Wave microwave synthesis system. Reaction conditions: The mixture was heated for 45 minutes at a temperature of 150 °C, a pressure 14.4 bar, ΔMW ≈ 200 W. The completeness of the reaction was determined using a gas chromatograph Agilent 7890B with a mass spectrometric detector 5977B. Antimicrobial and antifungal activity of 3-(2-bromophenyl)-5-(alkylthio)-4-phenyl-4H-1,2,4-triazoles (6 new compounds) was investigated. The most active compound with antifungal and antimicrobial effect was IIi. Substances IIa–IIe had moderate antimicrobial effect. Conclusions. New 3-(2-bromophenyl)-5-(alkylthio)-4-phenyl-4H-1,2,4-triazoles were synthesized by two methods. The antimicrobial and antifungal activity was investigated for the obtained compounds. The most active compound was 3-(2-bromophenyl)-5-(decylthio)-4-phenyl-4H-1,2,4-triazole (IIi). Some conclusions were drawn regarding the dependence of “structure – antimicrobial and antifungal effect”: the antimicrobial effect increased with the length of the carbon radical; changing the decyl radical to another one in the molecule 3-(2-bromophenyl)-5-(alkylthio)-4-phenyl-4H-1,2,4-triazole reduced antifungal activity.

APA, Harvard, Vancouver, ISO, and other styles

44

Shah, Tariq A., Zubair Ahmad, Niyaz A. Mir, M. Muneer, Nigam P. Rath, and Musheer Ahmad. "Correction: One step synthesis of highly functionalized thiazolo[3,2-b][1,2,4]triazole, triazolo[1,5-a]pyrimidine and triazolo[3,4-b][1,3,4]thiadiazine." RSC Advances 6, no. 12 (2016): 9437. http://dx.doi.org/10.1039/c6ra90004f.

Full text

Abstract:

Correction for ‘One step synthesis of highly functionalized thiazolo[3,2-b][1,2,4]triazole, triazolo[1,5-a]pyrimidine and triazolo[3,4-b][1,3,4]thiadiazine’ by Tariq A. Shah et al., RSC Adv., 2015, 5, 107931–107937.

APA, Harvard, Vancouver, ISO, and other styles

45

Tsyrenova, Biligma, and Valentine Nenajdenko. "Synthesis and Spectral Study of a New Family of 2,5-Diaryltriazoles Having Restricted Rotation of the 5-Aryl Substituent." Molecules 25, no. 3 (January 23, 2020): 480. http://dx.doi.org/10.3390/molecules25030480.

Full text

Abstract:

Efficient synthesis of 2,5-diaryl substituted 4-azido-1,2,3-triazoles by the reaction of sodium azide with dichlorosubstituted diazadienes was demonstrated. The optical properties of the prepared azidotriazoles were studied to reveal a luminescence maximum in the 360–420 nm region. To improve the luminescence quantum yields a family of 4-azido-1,2,3-triazoles bearing ortho-propargyloxy substituents in the 5 position was prepared. Subsequent intramolecular thermal cyclization permits to construct additional triazole fragment and obtain unique benzoxazocine derivatives condensed with two triazole rings. This new family of condensed heterocycles has a flattened heterocyclic system structure to provide more conjugation of the 5-aryl fragment with the triazole core. As a result, a new type of UV/“blue light-emitting” materials with better photophysical properties was obtained.

APA, Harvard, Vancouver, ISO, and other styles

46

Srinivasa Reddy, T., Hitesh Kulhari, V. Ganga Reddy, A. V. Subba Rao, Vipul Bansal, Ahmed Kamal, and Ravi Shukla. "Synthesis and biological evaluation of pyrazolo–triazole hybrids as cytotoxic and apoptosis inducing agents." Organic & Biomolecular Chemistry 13, no. 40 (2015): 10136–49. http://dx.doi.org/10.1039/c5ob00842e.

Full text

Abstract:

A series of pyrazolo–triazole hybrids were designed and synthesized by combining the 1,3-diphenyl pyrazole and triazole scaffolds to obtain (1-benzyl-1H-1,2,3-triazol-4-yl)(1,3-diphenyl-1H-pyrazol-4-yl)methanones.

APA, Harvard, Vancouver, ISO, and other styles

47

Gümüş, Mustafa Kemal. "Green Formation of Novel Pyridinyltriazole-Salicylidene Schiff Bases." Current Organic Synthesis 16, no. 2 (March 26, 2019): 309–13. http://dx.doi.org/10.2174/1570179416666181207145951.

Full text

Abstract:

Aim and Objective: In this work, water was used as solvent for the eco-friendly synthesis of imines under microwave irradiation. In the first step of the study, 5-pyridinyl-3-amino-1,2,4-triazole hydrochlorides were synthesized in the reaction of amino guanidine hydrochloride with different pyridine carboxylic acids under acid catalysis. A green method for 5-pyridinyl-3-amino-1,2,4-triazoles was developed with the assistance of microwave synthesis. In the second step, the eco-friendly synthesis of imines was achieved by reacting 5- pyridinyl-2H-1,2,4-triazol-3-amine hydrochlorides with salicylic aldehyde derivatives to produce 2-(5- pyridinyl-2H-1,2,4-triazol-3-ylimino)methyl)phenol imines. Materials and Methods: Microwave experiments were done using a monomode Anton Paar Monowave 300 microwave reactor (2.45 GHz). Reaction temperatures were monitored by an IR sensor. Microwave experiments were carried out in sealed microwave process vials G10 with maximum reaction volume of 10 mL. Results: When alternative methods were used, it was impossible to obtain good yields from ethanol. Nevertheless, the use of water was successful for this reaction. After 1-h microwave irritation, a yellow solid was obtained in 82% yield. Conclusion: In this work an eco-friendly protocol for the synthesis of Schiff bases from 5-(pyridin-2-, 3- or 4- yl)-3-amino-1,2,4-triazoles and substituted salicylic aldehydes in water under microwave irradiation was developed. Under the found conditions the high yields for the products were achieved at short reaction time and with an easy isolation procedure.

APA, Harvard, Vancouver, ISO, and other styles

48

Aguiar, Renata Alves, Marcos Gomes Cunha, Fernando Godinho Araújo, Luciana Celeste Carneiro, Edson Pereira Borges, and Valtemir José Carlin. "EFFICIENCY LOSS OF RECORDED FUNGICIDES FOR THE CONTROL OF ASIAN SOYBEAN RUST IN CENTRAL REGION OF BRAZIL." JOURNAL OF NEOTROPICAL AGRICULTURE 3, no. 2 (September 2, 2016): 41–47. http://dx.doi.org/10.32404/rean.v3i2.1066.

Full text

Abstract:

Due to grower allege of low efficiency of triazole fungicides in recent years in Central Brazil on the control of Asian soybean rust (Phakopsora pachyrhizi), this study was undertaken to demonstrate the efficiency loss of products registered for rust and applied alone and to evaluate the efficiency of fungicides mixtures. The trials were carried out in five locations in Brazil, in the 2009/10 growing season. The experimental design was completely randomized blocks with four replications. Ten mixtures of triazole + strobilurin and two applications of pure triazoles were evaluated and the control without application. The application of fungicides started in the R1/R2 stage or in any vegetative stage if infections occurred early. The mixtures of fungicides were effective in controlling Asian soybean rust. Application of sole triazole fungicides was less effective in controlling the rust than the mixtures of triazoles + strobilurins. The use of commercial mixtures of triazole with strobilurin for rust control is recommended.

APA, Harvard, Vancouver, ISO, and other styles

49

Rai, Vishakha, Kavyashree P., Sarvesh S. Harmalkar, Sundar N. Dhuri, and Mahagundappa R. Maddani. "1,6-Addition of 1,2,3-NH triazoles to para-quinone methides: Facile access to highly selective N¹ and N² substituted triazoles." Organic & Biomolecular Chemistry 20, no. 2 (2022): 345–51. http://dx.doi.org/10.1039/d1ob01717a.

Full text

Abstract:

Regioselective syntheses of N1 and N2 substituted triazoles via 1,6-addition of 1,2,3-NH triazole with p-QM were developed under mild reaction conditions. Isomerization of N1 to N2 substituted triazoles was also achieved in the presence of AlCl3.

APA, Harvard, Vancouver, ISO, and other styles

50

Govdi, Anastasia I., Polina V. Tokareva, Andrey M. Rumyantsev, Maxim S. Panov, Johannes Stellmacher, Ulrike Alexiev, Natalia A. Danilkina, and Irina A. Balova. "4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications." Molecules 27, no. 10 (May 17, 2022): 3191. http://dx.doi.org/10.3390/molecules27103191.

Full text

Abstract:

Cu-catalyzed 1,3-dipolar cycloaddition of ethyl 2-azidoacetate to iodobuta-1,3-diynes and subsequent Sonogashira cross-coupling were used to synthesize a large series of new triazole-based push–pull chromophores: 4,5-bis(arylethynyl)-1H-1,2,3-triazoles. The study of their optical properties revealed that all molecules have fluorescence properties, the Stokes shift values of which exceed 150 nm. The fluorescent properties of triazoles are easily adjustable depending on the nature of the substituents attached to aryl rings of the arylethynyl moieties at the C4 and C5 atoms of the triazole core. The possibility of 4,5-bis(arylethynyl)-1,2,3-triazoles’ application for labeling was demonstrated using proteins and the HEK293 cell line. The results of an MTT test on two distinct cell lines, HEK293 and HeLa, revealed the low cytotoxicity of 4,5-bis(arylethynyl)triazoles, which makes them promising fluorescent tags for labeling and tracking biomolecules.

APA, Harvard, Vancouver, ISO, and other styles

Journal articles on the topic 'Triazale'

Create a spot-on reference in APA, MLA, Chicago, Harvard, and other styles