Journal articles: 'Triazol'

1

Vashchenko, Oleksandr, Dmytro Khomenko, Roman Doroschuk, Ilona Raspertova, and Rostyslav Lampeka. "Synthesis of 3-(2-Hydroxyphenyl)-5-(2-Pyridinyl)-1,2,4-triazoles as a potential chelate ligand for Uranyl ion." French-Ukrainian Journal of Chemistry 8, no. 2 (2020): 1–6. http://dx.doi.org/10.17721/fujcv8i2p1-6.

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Two new uranyl complexes with the molecular formula [(UO2)(H2L1)](СH3OH) and [(UO2)(H3L2)](СH3OH) {H4L1 = 2-[5-[[5-[[5-(2-pyridyl)-1H-1,2,4-triazol-3‑yl]methyl]-1H-1,2,4-triazol-3-yl]methyl]-1H-1,2,4-triazol-3-yl]phenol and H5L2 = 2-[5-[[5-[[5-[[5-(2-pyridyl)-1H-1,2,4‑triazol-3-yl]methyl]-1H-1,2,4-triazol-3-yl]methyl]-1H-1,2,4-triazol-3-yl]methyl]-1H-1,2,4-triazol-3-yl]phenol)} have been synthesized. All compounds have been characterized by NMR and IR spectroscopy. With H4L1 and H5L2 uranyl ion forms mononuclear complexes. In [(UO2)(H3L2)](СH3OH) pyridyl nitrogen was uncoordinated and bonding of H5L2 was realized only through phenol oxygen and N4-nitrogens of triazole cycles.

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2

Nahlé, A., R. Salim, F. El Hajjaji, M. R. Aouad, M. Messali, E. Ech-chihbi, B. Hammouti, and M. Taleb. "Novel triazole derivatives as ecological corrosion inhibitors for mild steel in 1.0 M HCl: experimental & theoretical approach." RSC Advances 11, no. 7 (2021): 4147–62. http://dx.doi.org/10.1039/d0ra09679b.

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The present paper illustrates the investigation of two novel ecological triazole derivative corrosion inhibitors, namely ethyl 2-(4-phenyl-1H-1,2,3-triazol-1-yl) acetate [Tria-CO₂Et], and 2-(4-phenyl-1H-1,2,3-triazol-1-yl) acetohydrazide [Tria-CONHNH₂].

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3

Safonov, A. A. "Synthesis, physico-chemical properties of derivatives 3-(alkylthio)-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-4-amine." Farmatsevtychnyi zhurnal, no. 3-4 (August 14, 2018): 50–54. http://dx.doi.org/10.32352/0367-3057.3-4.16.03.

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Recently, the search for new compounds with high biological activity, which can be the basis for potential drugs, becomes topical for world scientists. A heterocyclic compound cause particular interest in this area as highly pharmacologically active compounds. Scientists extends interest due to the low toxicity and high reactivity 1,2,4-triazole of the system. It is proved that the combination of triazole nucleus with other heterocyclic systems, especially in the fifth position, causes increased biological effect, and, sometimes, the appearance of new pharmacological activities. The aim of the work was the synthesis of 3-(alkylthio)-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-4-amines and their derivatives, study of their physico-chemical properties. A series of new derivatives of the compounds 4-amino-5-R-1,2,4-triazole-3-thione (3-(alkylthio)-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-4-amines and N-R-idene)-3-(nonylthio)-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-4-amines) was synthesizes. The structure of compounds is set with modern physico-chemical methods of analysis (elemental analysis, 1H-NMR spectroscopy). Individuality is proved by HPLC-MS.

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4

Panchal, Ashvin D., and Pravin M. Patel. "Synthesis ofN-(5-(Substitutedphenyl)-4,5-dihydro-1H-pyrazol-3-yl)-4H-1,2,4-triazol-4-amine from 4-Amino-4H-1,2,4-triazole." E-Journal of Chemistry 8, no. 3 (2011): 1180–85. http://dx.doi.org/10.1155/2011/658708.

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N-(4H-1,2,4-Triazol-4-yl)acetamide (2) were prepared by reaction of 4-amino-4H-1,2,4-triazole (1) with acetyl chloride in dry benzene. It has been reacted with various aromatic aldehyde to afford 3-(substitutedphenyl)-N-(4H-1,2,4-triazol-4-yl)acrylamide (3a-e). The synthesis ofN-(5-substitutedphenyl)-4,5-dihydro-1H-pyrazol-3-yl)-4H-1,2,4-triazol-4-amine (4a-e) is achieved by the cyclisation of3a-ewith hydrazine hydrate in ethanol. The structures of synthesized compounds were characterized by1H NMR and IR spectroscopic studies. The purity of the compounds was checked by thin layer chromatography.

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5

Adamchyk, S. V., and A. L. Michal’chuk. "Potential aromatase inhibitors and antiestrogen agents based on stilbene and stilbazole derivatives." Proceedings of the National Academy of Sciences of Belarus, Chemical Series 56, no. 1 (March 19, 2020): 81–87. http://dx.doi.org/10.29235/1561-8331-2020-56-1-81-87.

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Abstract. Widely used forms of endocrine therapy for women with hormone-dependent breast cancer include blocking the biosynthesis of estrogens through using inhibitors of cytochrome P450 19A1 (aromatase). A series of new stilbene and stilbazole based aromatase inhibitors on are prepared. Z-isomers of 4-(2-(pyridin-4-yl)-1-(1H-1,2,4-triazol-1-yl)vinyl) benzonitrile, 4-(2-(pyridin-3-yl)-1-(1H-1,2,4-triazol-1-yl)vinyl)benzonitrile, 4-(2-(4-fluorophenyl)-1-(1H-1,2,4-triazol1-yl)vinyl)benzonitrile, 4-(2-(4-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)vinyl)benzonitrile, 4-(2-(4-bromophenyl)-1-(1H-1,2,4triazol-1-yl)vinyl)benzonitrile, 4-(2-(3,4-dimethoxyphenyl)-1-(1H-1,2,4-triazol-1-yl)vinyl)benzonitrile were prepared by condensation of 4-((1H-1,2,4-triazol-1-yl)methyl)benzonitrile and corresponding aldehyde in presence of strong base followed by dehydration of obtained alcohols. Isomerization to corresponded E-isomers was carried out in the presence of UV light.

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6

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.

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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.

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7

Bai, Shi-Qiang, Lu Jiang, David James Young, and T. S. Andy Hor. "Hybrid 1,2,3-Triazole Supported CuII Complexes: Tuning Assembly and Weak Interaction-Driven Crystal Growth." Australian Journal of Chemistry 69, no. 4 (2016): 372. http://dx.doi.org/10.1071/ch15650.

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Two new dinuclear CuII complexes [Cu2Cl4(L1)2] (1) and [Cu2Cl4(L2)2] (2) (L1 = 2-((4-(2-(cyclopentylthio)ethyl)-1H-1,2,3-triazol-1-yl)methyl)pyridine; L2 = 2-((4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl)benzonitrile) were synthesised and characterised by single-crystal X-ray diffraction (XRD), powder XRD, thermogravimetric analysis, elemental analysis and IR measurements. The picolyl-triazole ligand L1 coordinates in a chelate-bridging mode forming a dinuclear structure 1. The more rigid pyridyl-triazole ligand L2 chelates only, generating a chloride-bridged dinuclear complex 2. Both crystals of complexes 1 and 2 show dominant plate shapes that correlate with weak 2D H-bonding interactions in the lattice. A mononuclear structure (3, [CuCl2(L3)2]⋅6H2O, L3 = 3-((4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl)benzonitrile) yields block shape crystals that correlate with 3D H-bonding interactions. This study demonstrates tunable assembly at the molecular level and the relationship of crystal shape with weak lattice interactions.

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8

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.

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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)

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9

Childs, Bradley J., Donald C. Craig, Marcia L. Scudder, and Harold A. Goodwin. "Coordination of the Strong Field Terimine System 6-Triazol-3-yl-2,2′-bipyridine and Substituted Derivatives. Electronic and Structural Properties of Bis(ligand)iron(II) Complexes." Australian Journal of Chemistry 51, no. 10 (1998): 895. http://dx.doi.org/10.1071/c97202.

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A terminal pyridine ring in terpyridine has been replaced by a triazole or substituted triazole moiety to give the tridentates 6-(1,2,4-triazol-3-yl)-2,2´-bipyridine, 6-(1-methyl-1,2,4-triazol-3-yl)-2,2´-bipyridine, 6-(5-methyl-1,2,4-triazol-3-yl)-2,2´-bipyridine and 6-(1,5-dimethyl-1,2,4-triazol-3-yl)-2,2´-bipyridine. The effects of coordination of these on the electronic and structural properties of the [FeN6]2+ species are considered. The primary effect is a reduction in the ligand field but salts of the [FeN6]2+ derivatives are essentially low spin (singlet ground state) at room temperature. A small and temperature-dependent population of quintet state species is indicated by Mössbauer spectra but in no instance is a complete singlet → quintet transition observed up to 383 K. The electronic spectra of the [FeN6]2+ species are similar to that of [Fe(trpy)2]2+ but the energy of the charge-transfer transition is higher, indicating less effective metal ion → donor π-interaction than in the terpyridine complex. Consistent with this, the Mössbauer isomer-shift values are greater than for [Fe(trpy)2]2+ and the E½ values for the [FeN6]3+ /[FeN6]2+ couples are less positive than for [Fe(trpy)2]2+. Structural data reveal average Fe–N distances normal for low-spin iron(II) but with greater distortion of the coordination environment than in [Fe(trpy)2]2+. When present, the >NH group of the triazole moiety is hydrogen-bonded to solvate water and the anion in the hydrated tetrafluoroborate salts. Bis(6-(1,2,4-triazol-3-yl)-2,2´-bipyridine)iron(II) tetrafluoroborate tetrahydrate: monoclinic, space group P21/c, a 15·917(7), b 18·432(5), c 10·845(5) Å, β 94·36(2)°, Z 4; bis(6-(1-methyl-1,2,4-triazol-3-yl)-2,2´-bipyridine)iron(II) tetrafluoroborate: triclinic, space group P−1, a 11·68(1), b 11·96(2), c 12·46(2) Å, α 82·93(8), β 72·30(9), γ 68·49(10)°, Z 2; bis(6-(5-methyl-1,2,4-triazol-3-yl)-2,2´-bipyridine)iron(II) tetrafluoroborate monohydrate: monoclinic, space group P21/c, a 10·715(4), b 25·818(5), c 11·039(4) Å, β 90·08(2)°, Z 4; bis(6-(1,5-dimethyl-1,2,4-triazol-3-yl)-2,2´-bipyridine)iron(II) triflate tetrahydrate: orthorhombic, space group P bcn; a 20·654(6), b 11·618(3), c 16·080(6) Å, Z 4.

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10

Nami, Navabeh, Mehdi Forozani, Vida Khosravimoghadam, and Rahmatallah Taherinasab. "Synthesis and Characterization of Mono- and Bicycle Heterocyclic Derivatives Containing 1, 2,4-Triazole, 1,3,4-Thiadiazine and 1,3-Thiazole Rings." E-Journal of Chemistry 9, no. 1 (2012): 161–66. http://dx.doi.org/10.1155/2012/867637.

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Reaction of tartaric acid with thiocarbohydrazide(2)and thiosemicarbazide(6)afforded 1,2-bis(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)-ethane-1,2-diol(3)and 1,2-bis(5-mercapto-4H-1,2,4-triazol-3-yl)-ethane-1,2-diol(7). Reaction of compounds3and7with DMAD (dimethylacety lendi carboxylate) and DEAD (diethylacetylendicarboxylate) gave 1,2-bis(7-[(z)-methoxycarbonylmethylen]-5,6-dihydro-5H-6-one-[1,2,4] riazolo[3,4-b] [1,3,4] thiadiazin-3-yl)-ethan-1,2-diol(4), 1,2-bis(7-[(z)-ethoxycarbonylmethylen] -5,6-dihydro -5H-6-one-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-ethan-1,2- diol(5)and 1,2-bis(6-[(z)-methoxycarbonylmethylen]-5-oxo-[1,3]thiazolo[2,3-c] [1,2,4]triazol-3-yl)-ethan-1,2-diol(8)in good yields.

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11

Liu, Feng-Yi, Dong-Mei Zhou, Xiao-Lan Zhao, and Jun-Feng Kou. "Complexes of nickel(II) and copper(II) with 1,2,4-triazole-3-carboxylic acid and of cobalt(III) with 3-amino-1,2,4-triazole-5-carboxylic acid." Acta Crystallographica Section C Structural Chemistry 73, no. 11 (October 24, 2017): 1010–16. http://dx.doi.org/10.1107/s2053229617012943.

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Because of their versatile coordination modes and strong coordination ability for metals, triazole ligands can provide a wide range of possibilities for the construction of metal–organic frameworks. Three transition-metal complexes, namely bis(μ-1,2,4-triazol-4-ide-3-carboxylato)-κ3 N 2,O:N 1;κ3 N 1:N 2,O-bis[triamminenickel(II)] tetrahydrate, [Ni2(C3HN3O2)2(NH3)6]·4H2O, (I), catena-poly[[[diamminediaquacopper(II)]-μ-1,2,4-triazol-4-ide-3-carboxylato-κ3 N 1:N 4,O-[diamminecopper(II)]-μ-1,2,4-triazol-4-ide-3-carboxylato-κ3 N 4,O:N 1] dihydrate], {[Cu2(C3HN3O2)2(NH3)4(H2O)2]·2H2O} n , (II), (μ-5-amino-1,2,4-triazol-1-ide-3-carboxylato-κ2 N 1:N 2)di-μ-hydroxido-κ4 O:O-bis[triamminecobalt(III)] nitrate hydroxide trihydrate, [Co2(C3H2N4O2)(OH)2(NH3)6](NO3)(OH)·3H2O, (III), with different structural forms have been prepared by the reaction of transition metal salts, i.e. NiCl2, CuCl2 and Co(NO3)2, with 1,2,4-triazole-3-carboxylic acid or 3-amino-1,2,4-triazole-5-carboxylic acid hemihydrate in aqueous ammonia at room temperature. Compound (I) is a dinuclear complex. Extensive O—H...O, O—H...N and N—H...O hydrogen bonds and π–π stacking interactions between the centroids of the triazole rings contribute to the formation of the three-dimensional supramolecular structure. Compound (II) exhibits a one-dimensional chain structure, with O—H...O hydrogen bonds and weak O—H...N, N—H...O and C—H...O hydrogen bonds linking anions and lattice water molecules into the three-dimensional supramolecular structure. Compared with compound (I), compound (III) is a structurally different dinuclear complex. Extensive N—H...O, N—H...N, O—H...N and O—H...O hydrogen bonding occurs in the structure, leading to the formation of the three-dimensional supramolecular structure.

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12

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.

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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).

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13

Maliszewska-Guz, Alicja, Monika Wujec, Monika Pitucha, Maria Dobosz, Anna Chodkowska, Ewa Jagiełło-Wójtowicz, Liliana Mazur, and Anna E. Kozioł. "Cyclization of 1-{[(4-Methyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetyl}thiosemicarbazides to 1,2,4-Triazole and 1,3,4-Thiadiazole Derivatives and Their Pharmacological Properties." Collection of Czechoslovak Chemical Communications 70, no. 1 (2005): 51–62. http://dx.doi.org/10.1135/cccc20050051.

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By the reaction of 4-methyl-4H-1,2,4-triazole-3-thiol with ethyl bromoacetate, ethyl [(4-methyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetate (1) was obtained. This compound was converted to [(4-methyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetohydrazide (2). In the reaction of 2 with isothiocyanates, new thiosemicarbazides 3a-3g were obtained. The cyclization of 3a-3g in 2% aqueous solution of sodium hydroxide led to the formation of 4H-1,2,4-triazole-3(2H)-thione derivatives 4a-4g, whereas the cyclization in acid media led to the formation of 2-amino-1,3,4-thiadiazole derivatives 5a-5g. Molecular structure was confirmed by X-ray structure analysis of 3a, 4g, 5a and 5g. Compounds 4a, 4b and 4g were investigated pharmacologically to determine their effect on the central nervous system (CNS) in mice.

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Pavlov, Dmitry, Taisiya Sukhikh, Evgeny Filatov, and Andrei Potapov. "Facile Synthesis of 3-(Azol-1-yl)-1-adamantanecarboxylic Acids—New Bifunctional Angle-Shaped Building Blocks for Coordination Polymers." Molecules 24, no. 15 (July 26, 2019): 2717. http://dx.doi.org/10.3390/molecules24152717.

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For the first time, orthogonally substituted azole-carboxylate adamantane ligands were synthesized and used for preparation of coordination polymers. The angle-shaped ligands were prepared by the reaction of 1-adamantanecarboxylic acid and azoles (1H-1,2,4-triazole, 3-methyl-1H-1,2,4-triazole, 3,5-dimethyl-1H-1,2,4-triazole, 1H-tetrazole, 5-methyl-1H-tetrazole) in concentrated sulfuric acid. Variation of the solvent and substituents in azole rings allowed to prepare both 1D and 2D copper(II) and nickel(II) coordination polymers, [Cu2(trzadc)4(H2O)0.7]∙DMF∙0.3H2O, [Cu(trzadc)2(MeOH)]∙MeOH, [Ni(trzadc)2(MeOH)2] and [Cu2(mtrzadc)3(MeOH)]+NO3– (trzadc-3-(1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid; mtrzadc-3-(3-methyl-1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid) which were structurally characterized by single crystal X-ray diffraction. Complex [Cu(trzadc)2(MeOH)]∙MeOH was shown to act as a catalyst in the Chan-Evans-Lam arylation reaction.

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Yin, Ping, Jiaheng Zhang, Damon A. Parrish, and Jean'ne M. Shreeve. "Energetic fused triazoles – a promising C–N fused heterocyclic cation." Journal of Materials Chemistry A 3, no. 16 (2015): 8606–12. http://dx.doi.org/10.1039/c5ta01329a.

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A family of new energetic 3,6,7-triamino-7H-[1,2,4]triazolo[5,1-c][1,2,4]triazol-2-ium salts was developed as promising energetic materials with a high-nitrogen C–N fused framework as the energetic cation.

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Chandrasekhar, Attoor, Venkatachalam Ramkumar, and Sethuraman Sankararaman. "Palladium catalyzed carbonylative annulation of the C(sp2)–H bond of N,1-diaryl-1H-tetrazol-5-amines and N,4-diaryl-4H-triazol-3-amines to quinazolinones." Organic & Biomolecular Chemistry 16, no. 44 (2018): 8629–38. http://dx.doi.org/10.1039/c8ob02516a.

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Pd(ii) catalyzed direct C–H carbonylative annulation of N,1-diaryl-1H-tetrazol-5-amines and N,4-diaryl-4H-1,2,4-triazol-3-amines gave the corresponding triazole and tetrazole fused quinazolinones in good yields.

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Yilmaz, Fatih. "Synthesis and Characterisation of Some New Hybrid Molecules Containing Thiophene, Triazole and Coumarin Rings under Microwave Conditions." Journal of Chemical Research 42, no. 7 (July 2018): 361–65. http://dx.doi.org/10.3184/174751918x15314831778603.

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In this work, a new series of N‘-{[4-amino-5-oxo-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl}-2-oxo-2H-1-benzopyran-3-carbohydrazides (thiophene–triazole–coumarin hybrid molecules) was synthesised from the reaction of 2-[4-amino-5-oxo-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide and 3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-ones by using microwave irradiation and conventional heating procedures and their results were compared. The reaction was performed using a very small amount of organic solvent and without using a catalyst.

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Holota, Serhii, Yaroslav Shylych, Halyna Derkach, Olexandr Karpenko, Andrzej Gzella, and Roman Lesyk. "Synthesis of 4-(2H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one via Ring-Switching Hydrazinolysis of 5-Ethoxymethylidenethiazolo [3,2-b][1,2,4]triazol-6-one." Molbank 2018, no. 4 (October 1, 2018): M1022. http://dx.doi.org/10.3390/m1022.

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4-(1H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one (4) was synthesized with a yield of 55% via ring-switching hydrazinolysis of 5-ethoxymethylidenethiazolo[3,2-b][1,2,4] triazol-6-one (3) in ethanol medium. The initial 1H-[1,2,4]-triazole-3-thiol (1) was modified via a two-step reaction: S-alkylation with chloroacetic acid under Williamson reaction conditions, and further one-pot cyclization–condensation with triethylorthoformate in the acetic anhydride medium, yielding compound 3. The structures of compounds 3 and 4 were confirmed by LC-MS, NMR spectra and a single X-ray diffraction analysis (for compound 4).

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Bai, Hui, Xuelian Liu, Pengfei Chenzhang, Yumei Xiao, Bin Fu, and Zhaohai Qin. "Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety." Molecules 25, no. 24 (December 11, 2020): 5852. http://dx.doi.org/10.3390/molecules25245852.

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A series of novel 1,2,4-triazole derivatives containing oxime ether and phenoxy pyridine moiety were designed and synthesized. The new compounds were identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS). Compound (Z)-1-(6-(4-nitrophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a18) was further confirmed by X-ray single crystal diffraction. Their antifungal activities were evaluated against eight phytopathogens. The in vitro bioassays indicated that most of the title compounds displayed moderate to high fungicidal activities. Compound (Z)-1-(6-(4-bromo-2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a4) exhibited a broad-spectrum antifungal activities with the EC50 values of 1.59, 0.46, 0.27 and 11.39 mg/L against S. sclerotiorum, P. infestans, R. solani and B. cinerea, respectively. Compound (Z)-1-(6-(2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-benzyl oxime (5b2) provided the lowest EC50 value of 0.12 mg/L against S. sclerotiorum, which were comparable to the commercialized difenoconazole. Moreover, homologous modeling and molecular docking disclosed possible binding modes of compounds 5a4 and 5b2 with CYP51. This work provided useful guidance for the discovery of new 1,2,4-triazole fungicides.

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20

Shcherbyna, Roman, Volodymyr Parchenko, Boris Varynskyi, and Andriy Kaplaushenko. "The development of HPLC-DAD method for determination of active pharmaceutical ingredient in the potassium 2-((4-amino-5-(morpholinomethyl)-4H-1,2,4-triazol-3-yl)thio) acetate substance." Current Issues in Pharmacy and Medical Sciences 32, no. 1 (March 1, 2019): 5–9. http://dx.doi.org/10.2478/cipms-2019-0001.

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Abstract Derivatives of 1,2,4-triazole are actively researched by scientists and synthetic pharmacologists. The last studies have shown that potassium 2-((4-amino-5-(morpholinomethyl)-4H-1,2,4-triazol-3-yl)thio)acetate with low toxicity series exhibits antioxidant and hepatoprotective properties. Therefore, the purpose of this work was to develop a method for determining the API in the potassium 2-((4-amino-5-(morpholinomethyl)-4H-1,2,4-triazol-3-yl)thio)acetate substance using the method of high-performance liquid chromatography with diode array detection (HPLC-DAD). As a result of this work, it is shown that the developed method is specific and meets the requirements of linearity, accuracy and precision. The results of determining the contents of the API in real samples indicate that the method can be proposed to control the quality of the potassium 2-((4-amino-5-(morpholinomethyl)-4H-1,2,4-triazol-3-yl)thio)acetate substance.

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21

Rjabova, Jekaterina, Vitālijs Rjabovs, Antonio Moreno Vargas, Elena Clavijo, and Māris Turks. "Synthesis of novel 3-deoxy-3-C-triazolylmethyl-allose derivatives and evaluation of their biological activity." Open Chemistry 10, no. 2 (April 1, 2012): 386–94. http://dx.doi.org/10.2478/s11532-012-0002-9.

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AbstractRecently, monosaccharide-triazole conjugates have proved to possess a large variety of useful biological activities. This paper describes synthesis of a new series of 3-deoxy-3-C-triazolylmethyl-allose derivatives. These new compounds are obtained from acetonide-protected 3-deoxy-3-azidomethyl allose and commercial alkynes via Cu(I) catalyzed 1,3-dipolar cycloaddition. The obtained molecular scaffolds differ from those described earlier by the presence of a methylene linker (-CH2-) between the C(3) of allose and the triazole moiety. It was demonstrated that acetonide-protected monosaccharide, 3-deoxy-3-C-(4-phenyl-1H-1,2,3-triazol-1-yl)methyl-1,2:5,6-di-O-isopropylidene-α-d-allofuranose, inhibited α-L-fucosidase for 26% at 0.1 mM concentration, but a deprotected analog, 3-deoxy-3-C-(4-(4-tert-butylphenyl)-1H-1,2,3-triazol-1-yl)methyl-β-d-allofuranose, showed 15% inhibition of β-glucosidase at 1 mM concentration.

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22

Yang, Tingting, Xin Shi, Libing Guo, Shaohua Gu, Weiwei Zhang, Guiqing Xu, Wei Li, and Yuqin Jiang. "Design, synthesis, and antitumor activity of novel paeonol derivatives containing the 1,4-benzoxazinone and 1,2,3-triazole moieties." Journal of Chemical Research 43, no. 7-8 (July 2019): 241–47. http://dx.doi.org/10.1177/1747519819857479.

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A new series of paeonol derivatives containing the 1,4-benzoxazinone and 1,2,3-triazole moieties were synthesized and evaluated for their cytotoxicity in vitro against human non-small cell lung cancer NCI-H1299 cells and human cervical carcinoma HeLa cells. Among them, compared with that of paeonol, compounds 8-acetyl-4-{[(1-(5-chloro-2-nitrophenyl)-1 H-1,2,3-triazol-4-yl]methyl}-5-methoxy-2 H-1,4-benzoxazin-3(4 H)-one, 8-acetyl-4-[(1-mesityl-1 H-1,2,3-triazol-4-yl)methyl]-5-methoxy-2 H-1,4-benzoxazin-3(4 H)-one, and 8-acetyl-5-methoxy-4-{[(1-(naphthalen-1-yl)-1 H-1,2,3-triazol-4-yl]methyl}-2 H-1,4-benzoxazin-3(4 H)-one exhibited significant inhibitory activity toward the human non-small cell lung cancer NCI-H1299 cells (IC50 = 13.36 ± 0.003, 19.75 ± 0.3, 15.79 ± 0.05 μg mL−1). The last compound also exhibited significant inhibitory activity toward the human cervical carcinoma HeLa cells (IC50 = 19.73 ± 1.0 μg mL−1).

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23

Stankovičová, Henrieta, Renata Gašparová, Margita Lácová, and Jarmila Chovancová. "Reaction of 4-Oxochromene-3-carboxaldehydes with Primary Amides and Benzotriazole or 1H-1,2,4-Triazole." Collection of Czechoslovak Chemical Communications 62, no. 5 (1997): 781–90. http://dx.doi.org/10.1135/cccc19970781.

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N-[(6-substituted-4-oxochromen-3-yl)(1,2,4-triazol-3-yl)methyl]amides 5 and N-[(6-substituted-4-oxochromen-3-yl)(benzotriazol-1-yl)methyl]amides 6 were prepared by the reaction of 6-substituted 4-oxochromene-3-carboxaldehydes 1 with primary amides and 1H-1,2,4-triazole or 1H-benzotriazole. 6-Substituted 3-[hydroxy(1,2,4-triazol-1-yl)methyl]chromen-4-one 2 and 6-substituted 3-[hydroxy(benzotriazol-1-yl)methyl]chromen-4-one 3 were isolated as stable intermediates of these reactions. Beneficial effect of microwave irradiation on length of reaction time was observed. Some reactions of these derivatives with O, S, and N nucleophiles are described.

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24

Dobosz, Maria, Monika Pitucha, Izabela Dybala, and Anna E. Kozioł. "Cyclization of Semicarbazide Derivatives of 3-Methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazole-4-acetic Acid." Collection of Czechoslovak Chemical Communications 68, no. 4 (2003): 792–800. http://dx.doi.org/10.1135/cccc20030792.

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By the reaction of hydrazide of 3-methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazole-4-acetic acid (1) with isocyanates, 3-methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazole-4-acetosemicarbazide derivatives 2 were obtained. Cyclization of these compounds in the presence of 2% NaOH led to the formation of 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives 3, which was confirmed by X-ray analysis of 3b.

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25

Khomenko, D., R. Doroschuk, I. Odarych, I. Raspertova, and R. Lampeka. "CATECHOLASE ACTIVITY OF A COPPER(II) COMPLEX WITH THE 2-(5-(1,2,4)TRIAZOLE-1-ILMETHYL-1H-(1,2,4)-TRIAZOLE-3-IL)-PYRIDYL." Bulletin of Taras Shevchenko National University of Kyiv. Chemistry, no. 1 (57) (2020): 19–22. http://dx.doi.org/10.17721/1728-2209.2020.1(57).5.

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Methods of the synthesis of 2-(5-(1,2,4)triazol-1-ylmethyl-1H-(1,2,4)-triazol-3-yl)-pyridine and a binuclear copper complex are described. The structure of the complex is established by X-ray structural analysis. The complex is a centrosymmetric [Cu2(L)2(NO3)2·2H2O]·H2O dimer. The Cu-Cu distance is 4.0408 (3) Å. In the complex the ligand is in a deprotonated state. Due to this, the triazole fragment acts as a bridge between the two metal centers. Copper ions are in an octahedral environment. The equatorial plane is formed by three triazole nitrogen atoms and one pyridyl nitrogen atom. The axial positions are occupied by a water molecule and a nitrate ion. Isotropic patterns corresponding to binuclear copper particles of the [Cu2L2-H]+ composition were registered in the ESI mass spectra of the solution of the [Cu2(L)2(NO3)2(H2O)2]·H2O complex. These data confirm the presence of a binuclear complex in solution. The catecholoxidase activity of the binuclear copper (II) complex based on 2-(5-(1,2,4)triazol-1-ylmethyl-1H-(1,2,4)-triazol-3-yl)-pyridine was studied. The kinetics of model reactions of the catecholase type were investigated by the method of initial velocities using a model substrate of 3,5-di-tert-butyl catechol (3,5-DTBK). At low concentrations of 3,5-DTBK, the dependence of the initial oxidation rate on the concentration of the substrate is linear, which corresponds to the first order of the reaction on the substrate. However, the dependence graph at higher concentrations of 3,5-DTBK is nonlinear and indicates the saturation of the catalyst with the substrate. The form of the dependence of the initial reaction rate on the substrate concentration is explained within the framework of the Michaelis-Menten model, which well describes the behavior of natural metaloenzymes.

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26

Hamdi, Maamar, Oualid Talhi, Artur Silva, Nawel Lechani, Baya Kheddis-Boutemeur, Yacine Laichi, and Khaldoun Bachari. "Synthetic Approach Toward Heterocyclic Hybrids of [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazines." Synlett 29, no. 11 (April 23, 2018): 1502–4. http://dx.doi.org/10.1055/s-0036-1591991.

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The synthesis of novel heterocyclic [1,2,4]triazolo[3,4-b][1,3,4]thiadiazine hybrids by a bimolecular reaction of 2-(4-amino-5-mercapto-4H-[1,2,4]triazol-3-yl)phenol with an aromatic or heterocyclic α-bromoacetyl derivatives is described. This synthetic procedure starts from an unprotected phenol.

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27

Lakshman, Mahesh K., Manish K. Singh, Mukesh Kumar, Raghu Ram Chamala, Vijayender R. Yedulla, Domenick Wagner, Evan Leung, Lijia Yang, Asha Matin, and Sadia Ahmad. "Facile synthesis of 1-alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents, mechanistic studies, and synthetic applications." Beilstein Journal of Organic Chemistry 10 (August 19, 2014): 1919–32. http://dx.doi.org/10.3762/bjoc.10.200.

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(1H-Benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), 1H-benzo[d][1,2,3]triazol-1-yl 4-methylbenzenesulfonate (Bt-OTs), and 3H-[1,2,3]triazolo[4,5-b]pyridine-3-yl 4-methylbenzenesulfonate (At-OTs) are classically utilized in peptide synthesis for amide-bond formation. However, a previously undescribed reaction of these compounds with alcohols in the presence of a base, leads to 1-alkoxy-1H-benzo- (Bt-OR) and 7-azabenzotriazoles (At-OR). Although BOP undergoes reactions with alcohols to furnish 1-alkoxy-1H-benzotriazoles, Bt-OTs proved to be superior. Both, primary and secondary alcohols undergo reaction under generally mild reaction conditions. Correspondingly, 1-alkoxy-1H-7-azabenzotriazoles were synthesized from At-OTs. Mechanistically, there are three pathways by which these peptide-coupling agents can react with alcohols. From 31P{1H}, [18O]-labeling, and other chemical experiments, phosphonium and tosylate derivatives of alcohols seem to be intermediates. These then react with BtO− and AtO− produced in situ. In order to demonstrate broader utility, this novel reaction has been used to prepare a series of acyclic nucleoside-like compounds. Because BtO− is a nucleofuge, several Bt-OCH2Ar substrates have been evaluated in nucleophilic substitution reactions. Finally, the possible formation of Pd π–allyl complexes by departure of BtO− has been queried. Thus, alpha-allylation of three cyclic ketones was evaluated with 1-(cinnamyloxy)-1H-benzo[d][1,2,3]triazole, via in situ formation of pyrrolidine enamines and Pd catalysis.

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28

Weil, Matthias, and Markus Fürst. "Crystal structure of (1,4-diphenyl-4H-1,2,4-triazol-3-yl)phenylamine difluorophosphate, and a survey of the difluorophosphate anion (PO2F2 −)." Acta Crystallographica Section E Crystallographic Communications 76, no. 7 (June 2, 2020): 1003–6. http://dx.doi.org/10.1107/s2056989020006933.

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Nitron is the trivial name of (1,4-diphenyl-4H-1,2,4-triazol-3-yl)phenylamine (C20H16N4), a triazole derivative used as an analytical reagent for gravimetric analysis of the nitrate anion. The crystal structure of the difluorophosphate salt of Nitron, 3-anilino-1,4-diphenyl-1H-1,2,4-triazol-4-ium difluorophosphate, C20H17N4 +·PO2F2 −, is reported here. Within the protonated Nitron molecule, the triazole ring, one of the phenyl rings and the NHPh moiety are virtually co-planar, with the third phenyl ring inclined to the least-squares plane of the other three rings by 56.07 (3)°. Intermolecular N—H...O and C—H...O hydrogen bonds between cations and difluorophosphate anions lead to the formation of a three-dimensional network that is consolidated by additional π–π stacking interactions between the triazole ring and one of the phenyl rings. Database surveys on inorganic, metal–organic and organic structures comprising the tetrahedral PO2F2 group reveal mean bond lengths of P—O = 1.459 (27) Å, P—F = 1.530 (21) Å, and angles of O—P—O = 121.2 (2.9)°, O—P—F = 108.7 (6)°, and F—P—F = 98.5 (2.6)°, using a dataset of 67 independent PO2F2 − anions or PO2F2 entities.

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29

Youssif, Bahaa G. M., Yaseen A. M. Mohamed, Mohammed T. A. Salim, Fuyuhiko Inagaki, Chisato Mukai, and Hajjaj H. M. Abdu-Allah. "Synthesis of some benzimidazole derivatives endowed with 1,2,3-triazole as potential inhibitors of hepatitis C virus." Acta Pharmaceutica 66, no. 2 (June 1, 2016): 219–31. http://dx.doi.org/10.1515/acph-2016-0014.

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Abstract New derivatives of 2-thiobenzimidazole incorporating triazole moiety were synthesized, characterized and tested in vitro for antiviral activity against hepatitis C virus (HCV) and hepatitis B virus (HBV). Their cytotoxicity was determined by the reduction in the number of viable cell. All of the synthesized compounds are inactive against HBV and some showed activity against HCV. In particular, two compounds showed significant activity, 2-{4-[(1-benzoylbenzimidazol-2-ylthio)methyl]-1H-1,2,3-triazol-1-yl}-N-(p-nitro-phenyl)-acetamide (13) and 2-(4-{[1-(p-chlorobenzoyl)-benzimidazol-2-ylthio)methyl]-1H-1,2,3-triazol-1-yl}-N-(p-nitrophenyl)-acetamide (17). The results give an insight into the importance of the substituent at position 2 of benzimidazole for the inhibition of HCV.

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30

Nguyen Tien, Cong, Duc Tran Thi Cam, Ha Bui Manh, and Dat Nguyen Dang. "Synthesis and Antibacterial Activity of Some Derivatives of 2-Methylbenzimidazole Containing 1,3,4-Oxadiazole or 1,2,4-Triazole Heterocycle." Journal of Chemistry 2016 (2016): 1–6. http://dx.doi.org/10.1155/2016/1507049.

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5-[(2-Methyl-1H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazole-2-thiol or 5-[(2-methyl-1H-benzimidazol-1-yl)methyl]-4-(4-methylphenyl)-1,2,4-triazol-3-thiol which were prepared starting from 2-methylbenzimidazole in the reaction with appropriateN-aryl-2-chloroacetamides afforded two series ofN-aryl-2-{5-[(2-methyl-1H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazol-2-yl}sulfanylacetamides andN-aryl-2-{5-[(2-methyl-1H-benzimidazol-1-yl)methyl]-4-(4-methylphenyl)-4H-1,2,4-triazol-3-ylthio}acetamides, respectively. The structures of the compounds were elucidated on the basis of IR, MS,1H-NMR, and13C-NMR spectral data. The compounds containing 1,3,4-oxadiazole or 1,2,4-triazole heterocycle also were tested for their antimicrobial activity against bacteria, mold, and yeast.

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Mao, Wen-Zhao, and Jing Chen. "A one-dimensional coordination polymer of 5-(pyridin-2-yl)-3,3′-bi(4H-1,2,4-triazole) with Cd(NO3)2." Acta Crystallographica Section C Crystal Structure Communications 69, no. 9 (August 3, 2013): 1006–9. http://dx.doi.org/10.1107/s0108270113019999.

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In the title coordination polymer,catena-poly[[(methanol-κO)(nitrato-κO)cadmium(II)]-μ-3-(pyridin-2-yl)-5-(1H-1,2,4-triazol-5-yl)-4H-1,2,4-triazol-4-ido], [Cd(C9H6N7)(NO3)(CH3OH)]n, the asymmetric unit is composed of one CdIIcentre, one nitrate anion, one deprotonated 5-(pyridin-2-yl)-3,3′-bi(4H-1,2,4-triazole) ligand, denoted HBPT−, and one coordinated methanol molecule. Each CdIIion shows an octahedral geometry and is surrounded by four N atoms from two HBPT−ligands in the equatorial plane, and by two O atoms from a monodentate nitrate ligand and a methanol ligand. The structure is a one-dimensional polymeric chain, which is further extended to a three-dimensional supramolecular networkviaa combination of hydrogen-bonding and aromatic stacking interactions.

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32

Wurfer, Flavius-Gabriel, and Valentin Badea. "(R,S)-2-{[4-(4-Methoxyphenyl)-5-phenyl-4H-1,2,4-triazol-3-yl] thio}-1-phenyl-1-ethanol." Molbank 2021, no. 2 (June 8, 2021): M1231. http://dx.doi.org/10.3390/m1231.

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4-(4-Methoxyphenyl)-5-phenyl--4H-1,2,4-triazole-3-thiol (4) was alkylated to 2-{[4-(-4-methoxyphenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]thio}-1-phenylethan-1-one (5) in alkaline conditions using 2-bromo-1-phenylethanone. The alkylated compound (5) was reduced at the carbonyl group to the corresponding racemic secondary alcohol with an asymmetric carbon, (R,S)-2-{[4-(4-methoxyphenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol (6). Both synthesized compounds, ketone (5) and secondary alcohol (6), are new and have not been reported yet in the literature. All the synthesized compounds were characterized by IR, 1D and 2D NMR 1H-1H, 1H-13C and 1H-15N-NMR spectroscopy and by elemental analysis.

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33

Safonov, A. A. "Synthesis, physico-chemical properties of 2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)acetohyd-razides." Farmatsevtychnyi zhurnal, no. 5 (August 14, 2018): 31–36. http://dx.doi.org/10.32352/0367-3057.5.16.03.

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The value of the class of 1,2,4-triazole derivatives to create a low-toxic and highly active substances is huge. There are a lot of facts about the high biological activity among a number of substances. The 2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)acetohydrazides derivatives causes of particular interest in this direction. The aim of the work was to synthesize 2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)acetohydrazides and their derivatives, studying of their physico-chemical properties. 2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)-N'-R-acetohydrazides were synthesized by of 2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)acetohydrazides with aldehydes and ketones in the i-propanol with the addition of hydrochloric acid. The melting point was determined by an automatic device for determining the melting point OptiMelt Stanford Research Systems MPA100 (US). The elemental composition of compounds found in elemental analyzer Elementar Vario L cube (CHNS) (standard ‒ sulfonamides). Chromatography-mass spectral studies conducted on gas-liquid chromatograph Agilent 1260 Infinity HPLC with equipped mass spectrometer Agilent 6120, 1H-NMR-spectra were registered on spectrometer Mercury 400 A series of new 2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)-N'-R-acetohydrazides derivatives were synthesized, R-2-chloro-6-fluorobenzylidene, 3-nitrobenzylidene, 4-hydroxybenzylidene, 2-nitrobenzylidene, 2,4-dimethylbenzylidene, 3,5-dimethoxybenzylidene, 3-bromo-4-fluorobenzylidene, 2,3-dimethoxybenzylidene, 2-bromobenzylidene, 2-fluorobenzylidene, 4-(dimethylamino)benzylidene, pyridin-2-ylmethylene, 5-nitrofuran-2-ylmethylene, 4-methoxybenzylidene, 2-hydroxybenzylidene, 4-methoxyphenyl)ethylidene, 1-(thiophen-2-yl)ethylidene. The structure of these compounds was established by modern physico-chemical analysis methods (elemental analysis, 1H-NMR spectroscopy). Individuality was proved by HPLC-MS.

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34

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.

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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.

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35

Xu, Xue-Tang, Xian-Li Ma, Wen-Gui Duan, Li Chen, Bo Cen, Qi-Jin Mo, and Jian-Yi Wang. "Synthesis and fungicidal activity of dehydroabietyl-1,2,4-triazolo-thiazolidinones." Holzforschung 67, no. 1 (January 1, 2013): 107–12. http://dx.doi.org/10.1515/hf-2012-0026.

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Abstract In search of novel potent bioactive compounds, a series of novel dehydroabietic acid derivatives bearing 1,2,4-triazolo-thiazolidinone moieties were designed and synthesized. Seven compounds were synthesized of the type 6-substituted benzylidene-3-dehydroabietyl-thiazolo[2,3-c][1,2,4]triazol-5-ones. To this purpose a condensation reaction was performed with 3-dehydroabietyl-thiazolo[2,3-c][1,2,4]triazol-5-one and various aromatic aldehydes. All the title compounds were analyzed and characterized by means of IR, MS, 1H NMR, 13C NMR, and elemental analysis. A preliminary bioassay showed that, at a concentration of 50 μg ml-1, the target compounds exhibited the best fungicidal activity against Fusarium graminearum (F. graminearum) of the five fungi tested (F. oxysporum f. cucumerinum, Alternaria solani, Physalospora piricola, Cercospora arachidicola, and F. graminearum).

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Miethchen, Ralf, Helga Albrecht, and Edeltraud Rachow. "Die Jodierung von 1,2,4-Triazol und 1,2,3-Triazol zu 3, 5-Dijod-1,2,4-triazol bzw. 4,5-Dijod-1,2,3-triazol." Zeitschrift für Chemie 10, no. 6 (September 1, 2010): 220–21. http://dx.doi.org/10.1002/zfch.19700100606.

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37

Hajri, Azhar, and Mohamed Lamjed Marzouki. "Simple and efficient approach to synthesis of [1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine- 1-oxides from N-triazol-3-ylamidines." Heterocyclic Communications 23, no. 2 (April 1, 2017): 97–100. http://dx.doi.org/10.1515/hc-2017-0003.

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AbstractA facile method for the synthesis of [1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxides 3a–h is presented. The approach involves a reaction between N-triazol-3-ylamidines 2a–h and thionyl chloride in the presence of pyridine. The structures of the synthesized compounds were confirmed by spectral studies including IR, 1H NMR, 13C NMR, MS and elemental analysis.

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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.

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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.

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39

Unnamatla, M. V. Basavanag, Marco A. García-Eleno, and Erick Cuevas Yáñez. "Ionic Liquid Mediated Ugi/SN2 Cyclization: Synthesis of 1,2,3-Triazole Containing Novel 2,5-Diketopiperazines." Proceedings 41, no. 1 (November 16, 2019): 75. http://dx.doi.org/10.3390/ecsoc-23-06657.

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The Ugi four-component reaction is versatile multicomponent reaction for generation of complex diversity, herein, we developed a novel methodology by using 4-((1-((tetrahydrofuran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methoxy)benzaldehyde as one of the components in Ugi 4CR that contains 1,2,3-triazole moiety which is a privileged molecule in medicinal chemistry to obtain Ugi adducts under room temperature ionic liquids as medium of solvent, then followed SN2 pathway cyclization to get triazole containing 2,5-diketopiperazine derivatives in good yield using basic ionic liquids as a catalyst.

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40

Szpakiewicz, Barbara, and Maria Grzegożek. "Vicarious nucleophilic amination of nitroquinolines with 4-amino-1,2,4-triazole." Canadian Journal of Chemistry 86, no. 7 (July 1, 2008): 682–85. http://dx.doi.org/10.1139/v08-051.

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3-, 5-, 6-, 7- and 8-Nitroquinolines react with 4-amino-1,2,4-triazole in basic medium (potassium tert-butoxide-dimethyl sulfoxide) giving amino products of the vicarious nucleophilic substitution (VNS) of hydrogen, predominantly at ortho position to the nitro group, except 8-nitroquinoline, which reacts at para position. Additionally, furazano[3,4-f]- and furazano[3,4-h]quinoline were obtained in the case of 5- and 8- nitroquinoline, respectively. 2-Nitroquinoline was aminated to 2-quinolino(1,2,4-triazol-4-yl)amine in these conditions.Key words: nitroquinolines, vicarious nucleophilic substitution (VNS), 4-amino-1,2,4-triazole.

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41

Sarragiotto, Maria, George Brand, Carla Gomes, Willian Costa, Mary Foglio, and Ana Ruiz. "Synthesis and Antitumor Activity of Novel 1-Substituted 3-(4,5-Substituted 1,2,4-Triazol-3-yl)-β-carboline Derivatives." Synthesis 51, no. 02 (September 26, 2018): 573–77. http://dx.doi.org/10.1055/s-0037-1610291.

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Schiff bases, 1,2,4-triazolo[4,3-d][1,2,3,4]thiatriazoles, and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles carrying the β-carboline nucleus were synthesized from 3-(4-amino-5-mercapto-1,2,4-triazol-3-yl)-β-carbolines. The compounds were evaluated for their in vitro antitumor activity against eight human cancer cell lines. The 1,2,4-triazolo[4,3-d][1,2,3,4]thiatriazole derivatives showed a broad spectrum of antitumor activity, with GI50 values lower than 13 μM for all cell lines tested. In general, all tested compounds showed potent activity against the breast (MCF-7) cancer cell line, with GI50 values in the range of 2.07 to 4.58 μM.

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42

Jia, Li-Hui, Zu-Li Liu, and Wei Liu. "4-(1H-1,2,4-Triazol-3-yl)-4H-1,2,4-triazole monohydrate." Acta Crystallographica Section E Structure Reports Online 63, no. 5 (April 30, 2007): o2766. http://dx.doi.org/10.1107/s1600536807020272.

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43

Moreno-Fuquen, Rodolfo, Kevin Arango-Daraviña, Diana Becerra, Juan-Carlos Castillo, Alan R. Kennedy, and Mario A. Macías. "Catalyst- and solvent-free synthesis of 2-fluoro-N-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide through a microwave-assisted Fries rearrangement: X-ray structural and theoretical studies." Acta Crystallographica Section C Structural Chemistry 75, no. 3 (February 25, 2019): 359–71. http://dx.doi.org/10.1107/s2053229619002572.

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An efficient approach for the regioselective synthesis of (5-amino-3-methylsulfanyl-1H-1,2,4-triazol-1-yl)(2-fluorophenyl)methanone, C10H9FN4OS, (3), from the N-acylation of 3-amino-5-methylsulfanyl-1H-1,2,4-triazole, (1), with 2-fluorobenzoyl chloride has been developed. Heterocyclic amide (3) was used successfully as a strategic intermediate for the preparation of 2-fluoro-N-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide, C10H9FN4OS, (4), through a microwave-assisted Fries rearrangement under catalyst- and solvent-free conditions. Theoretical studies of the prototropy process of (1) and the Fries rearrangement of (3) to provide (4), involving the formation of an intimate ion pair as the key step, were carried out by density functional theory (DFT) calculations. The crystallographic analysis of the intermolecular interactions and the energy frameworks based on the effects of the different molecular conformations of (3) and (4) are described.

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44

Bihdan, O. A., and V. V. Parchenko. "Synthesis and physical-chemical properties of some 5-(3-fluorophenyl)-4-methyl-1,2,4-triazole-3-thiol derivatives." Farmatsevtychnyi zhurnal, no. 2 (August 14, 2018): 38–47. http://dx.doi.org/10.32352/0367-3057.2.17.05.

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There are engaged scientists practically from all over the world to the 1,2,4-triazole system research but the greatest attention deserve the achievements of domestic scientists who managed from the very beginning to register new original medicines in Ukraine. There is no doubt that the original attempt of combining various typical fragments with the nucleus of 1,2,4-triazole is gaining popularity among researchers. The purpose of our work was to synthesized and investigate a row of new 5-(3-fluorophenyl)-4-methyl-1,2,4-triazole-3-thiols by a Sulfur atom, to study the physical-chemical properties of previously unsubscribed compounds. The chemical names of the compounds are given in accordance with the IUPAC nomenclature (1979) and the IUPAC recommendations (1993). Investigations of the physical-chemical properties of the obtained compounds were carried out according to the methods which are given in the State Pharmacopoeia of Ukraine. The melting point was determined on an automatic device for determining the melting point OptiMelt Stanford Research Systems MPA100 (USA). The elemental structure of the new compounds was established on the element analyzer Elementar Vario L cube (CHNS) (standard - sulfanilamide). The data of elemental analysis correspond to the calculated. The 1Н NMR-spectra of the compounds were recorded using a «Mercury 400» spectrometer, the solvent DMSO-d6, the internal standard – tetramethylsilane (TMS) and decrypted using the SpinWorks computer program. Chromate-mass spectra were recorded on an Agilent 6890N/5973N/FID spectrometer produced by Agilent Technologies with a Dean microflow switch. By the experiment results there were obtained eleven previously unidentified individual compounds light yellow and white color which are soluble in organic solvents and insoluble in water. The crystallization process was carried out in isopropanol. Using a complex approach with the use of modern physical-chemical methods of analysis we confirmed the structure of 5-(3-fluorophenyl)-4-methyl-1,2,4-triazole-3-thiol, 3-alkylthio-5-(3-fluorophenyl)-4-methyl-1,2,4-triazole, 1,4-bis((5-(3-fluorophenyl)-4-methyl-1,2,4-triazole-3-yl)thio)propane and 1,4-bis((5-(3-fluorophenyl)-4-methyl-1,2,4-triazole-3-yl)thio)butane. The individuality of the synthesized compounds was confirmed chromatographically, the constants peaks of the pseudo molecular ions of the synthesized compounds coincide with the calculated values of the molecular masses. We first synthesized 5-(3-fluorophenyl)-4-methyl-1,2,4-triazol-3-thiol which was further used as a starting material in the synthesis of new 3-alkylthio-5-(3-fluorophenyl)-4-methyl-1,2,4-triazole, 1,4-bis((5-(3-fluorophenyl)-4-methyl-1,2,4-triazol-3-yl)thio)propane and 1,4-bis((5-(3-fluorophenyl)-4-methyl-1,2,4-triazol-3-yl)thio)butane. Complex physical-chemical methods of analysis confirmed the structure of synthesized compounds.

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45

Lobo, Prajwal L., Boja Poojary, Kumsi Manjunatha, and Nalilu Suchetha Kumari. "Synthesis and Antimicrobial Evaluation of Some New 2-(6-Oxo-5,6- dihydro[1,3]thiazolo[3,2-b]-2-aryloxymethyl-1,2,4-triazol-5-yl)-Narylacetamides." Zeitschrift für Naturforschung B 65, no. 5 (May 1, 2010): 617–24. http://dx.doi.org/10.1515/znb-2010-0512.

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A series of 2-(6-oxo-5,6-dihydro[1,3]thiazolo[3,2-b]-2-aryloxymethyl-1,2,4-triazol-5-yl)-Narylacetamides 6 were synthesized in good yield by condensing 5-aryloxymethyl-4H-1,2,4-triazole- 3-thiol 5 with various substituted N-phenyl-maleimides in acetic acid media. The newly synthesized compounds were characterized by spectral data and tested for their in vitro antibacterial and antifungal activity against a variety of microorganisms.

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46

Castiñeiras, Alfonso, Isabel García-Santos, and Manuel Saa. "Synthesis and Structural Assessment of Methyl 2-(4-Phenyl-5-(Pyridin-2-yl)-4H-1,2,4-Triazol-3-yl)Thioacetate (phpy2NS) and Its Complex with HgCl2." Proceedings 2, no. 14 (September 7, 2018): 1115. http://dx.doi.org/10.3390/iecc_2018-05249.

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Reaction of 2-cyanopyridine with N-phenylthiosemicarbazide afforded the 4-phenyl-5-(pyridin-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione. Methyl 2-((4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl)thio)acetate (phpy2NS, 1), derived from this 1,2,4-triazole-3-thione, was obtained by reaction with chloroacetic acid followed by an acid-catalyzed esterification of the carboxylic acid with methyl alcohol. Synthesis of a Hg(II) complex, [Hg(phpy2NS)Cl2] (2), has been performed using the ligand (1) and HgCl2. The molecular and supramolecular structures of the ligand and the complex were studied by X-ray diffractometry.

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47

Chalenko, N. M., P. A. Bezugly, A. O. Sirova, I. S. Chekman, and A. M. Demchenko. "Synthesis and antiexudative activityof pyrolin derivatives 2 - ((4-amino-5- (furan-2-yl)-1,2,4-triazol-4H-3-il)-sulfanil)-N-acetamides." Farmatsevtychnyi zhurnal, no. 5 (October 29, 2019): 65–74. http://dx.doi.org/10.32352/0367-3057.5.19.07.

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The continuous research of new effective drugs is associated with a significant number of diseases, pathological conditions. Conventional treatment with existing drugs could be ineffective, or addictive, and have a large number of side effects. Therefore, the aim of modern pharmacy is to minimize the toxicity of drugs and create new modern domestic medicine that would be more effective in relation to their activity and relatively non-toxic. Derivatives of 1,2,4-triazol have considerable synthetic, pharmacological potential. That’s why study of the synthetic methods of the new structures obtain, its physical, physico-chemical, biological properties may become the basic for their spector of the synthesized derivatives and biological activity widening. The aim of the work: choice on the investigation ground in silico the basic structures 1,2,4-triazol-3-thione and the special purpose synthesis of the new potential biological active compounds, definition its structure and physic-chemical properties mark of antiexudative activity. The synthesis of pyroline derivatives of 2-((4-amino-5-(furan-2-il)-1,2,4-triazol-4H-3-il)-sulfanyl)-N-acetamides was accomplished by stages. The article describes the synthesis of new pyrolin derivatives 2-((4-amino-5(furan-2-yl)-1,2,4-triazol-4H-3-il)-sulfanyl)-N-acetamide. Acetamides were obtained by alkylation of 2-((4-amino-5(furan-2-yl)-1,2,4-triazol-3-thione N-aryl-substituted α-chloroacetamides in the presence of KOH. Using Paal-Knorr condensation of the amino group at 4th position of the triazole ring modified into pyrolium fragment. Physical and chemical characteristics, chemical structure and anti-exudative activity of the obtained compounds were established. Anti-exudative activity of compounds was investigated in the experiments on the white rats in the doses 10 mg/kg comparately with reference drug-diclophenac natrium in formalin edema modulation. The paw size was measured by pletismography before drugs introduction. For the first time 24 compounds have been synthesized: 4 pyroline derivatives 2-((4-amino-5-(furan-2-il)-1,2,4-triazol-4H-3-il)-sulfanyl)-N-acetamides. In 91% of the new synthesized derivatives the antiexudative properties have been found, 5 compounds (10.9, 10.10, 10.15, 10.21, 10.1) by anti-exudative activity have exceeded the reference drug. It is considered that the investigations of these compounds by presence or absence analgesics activities are perspective.

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48

Fang, Zi-Yi, Li Zhang, Jian-Ping Ma, Long Zhao, Shi-Ling Wang, Nan-Hua Xie, Yi-Qin Liu, Xiao-Ying Guo, and Jie Qin. "Dinuclear cobalt and nickel complexes of a mercaptoacetic acid substituted 1,2,4-triazole ligand: syntheses, structures and urease inhibitory studies." Acta Crystallographica Section C Structural Chemistry 75, no. 12 (November 25, 2019): 1658–65. http://dx.doi.org/10.1107/s2053229619015602.

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Because of its versatile coordination modes and strong coordination ability, the mercaptoacetic acid substituted 1,2,4-triazole 2-{[5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid (H2L) was synthesized and characterized. Treatment of H2L with cobalt and nickel acetate afforded the dinuclear complexes {μ-3-[(carboxylatomethyl)sulfanyl]-5-(pyridin-2-yl)-4H-1,2,4-triazol-4-ido-κ2 N 1,N 5:N 2,O}bis[aqua(methanol-κO)cobalt(II)] methanol disolvate, [Co2(C9H6N4O2S)2(CH3OH)2(H2O)2]·2CH3OH (1), and {μ-3-[(carboxylatomethyl)sulfanyl]-5-(pyridin-2-yl)-4H-1,2,4-triazol-4-ido-κ2 N 1,N 5:N 2,O}bis[diaquanickel(II)] methanol disolvate dihydrate, [Ni2(C9H6N4O2S)2(H2O)4]·2CH3OH·2H2O (2), respectively. Complex 1 crystallized in the monoclinic space group P21/c, while 2 crystallized in the tetragonal space group I41/a. Single-crystal X-ray diffraction studies revealed that H2L is doubly deprotonated and acts as a tetradentate bridging ligand in complexes 1 and 2. For both of the obtained complexes, extensive hydrogen-bond interactions contribute to the formation of their three-dimensional supermolecular structures. Hirshfeld surface analysis was used to illustrate the intermolecular interactions. Additionally, the urease inhibitory activities of 1, 2 and H2L were investigated against jack bean urease, where the two complexes revealed strong urease inhibition activities.

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49

Varynskyi, Borys, and Andriy Kaplaushenko. "Metabolism study of morpholinium 2- ((4- (2-methoxyphenyl)-5-(pyridin-4-yl) -4H-1,2,4-triazole-3-yl)thio) acetate." Current Issues in Pharmacy and Medical Sciences 33, no. 2 (June 1, 2020): 72–75. http://dx.doi.org/10.2478/cipms-2020-0014.

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AbstractAim. The purpose of this study is to reveal the determination of the structure of the main metabolite of morpholinium 2-(4-(2-methoxyphenyl)-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-yl)thio)acetate (an active pharmaceutical ingredient – API) by way of chromatography through mass spectrometry detection, utilizing the liquid chromatography system Agilent 1260 Infinity and mass spectrometry detector (single quadrupole detector Agilent 6120). In the work, the graph of the change in the area of the peak of the metabolite from time after the introduction of the API solution was constructed. Moreover, the charges on the atoms of 2-((4-(2-methoxyphenyl)-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio) acetate were calculated and the structure of the methyl derivative was proposed. We saw that the methylation of the active substance during metabolism formed a 5-((carboxymethyl)thio)-4-(2-methoxyphenyl)-1-methyl-3-(pyridin-4-yl)-4H-1,2,4-triazol-1-um cation through N-methyltransferase.

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50

Raabe, Gerhard, Klaus Breuer, Dieter Enders, and J. Henrique Teles. "The Role of Conjugative Interaction in Stable Carbenes of the 1,2,4-Triazol-5-ylidene Type and their Energy of Dimerization. An Ab Initio Study." Zeitschrift für Naturforschung A 51, no. 1-2 (February 1, 1996): 95–101. http://dx.doi.org/10.1515/zna-1996-1-214.

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Abstract The role of conjugative interaction in stable carbenes of the 1,2,4-triazol-5-ylidene type was studied at different levels of ab initio theory employing model compounds. In the case of parent 4,5-dihydro-1 H-1,2,4-triazol-5-ylidene this type of interaction was found to be of similar importance as in 1,2,4-triazole and pyridine.Five stationary points were located on the hypersurface of the dimer (C2N3H3)2 . ΔE for all considered dimerization reactions was found to be negative, and the change of energy associated with the formation of the most stable isomer is about -9.5 kcal/mol. In spite of a high value for the singlet-triplet gap of about 90 kcal/mol for the carbene, the heavy atom skeleton of the most stable dimer is close to planarity. This finding is in perfect accordance with the predictions of other authors regarding the geometry of dimers from singlet carbenes stabilized by π-conjugation.

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Journal articles on the topic 'Triazol'

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