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Journal articles on the topic 'TRIAZOLO-PYRIMIDINE'

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Author: Grafiati

Published: 1 April 2023

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1

Jakubowski, Mateusz, Iwona Łakomska, Adriana Kaszuba, Andrzej Wojtczak, Jerzy Sitkowski, and Andrzej A. Jarzęcki. "Factors Affecting the Stability of Platinum(II) Complexes with 1,2,4-Triazolo[1,5-a]pyrimidine Derivatives and Tetrahydrothiophene-1-Oxide or Diphenyl Sulfoxide." International Journal of Molecular Sciences 23, no. 7 (March 26, 2022): 3656. http://dx.doi.org/10.3390/ijms23073656.

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The platinum(II) complexes of general formula [PtCl2(dstp)(S-donor)] were dstp 5,7-dimethyl-1,2,4-triazolo[1,5-a]-pyrimidine (dmtp), 5,7-ditertbutyl-1,2,4-triazolo[1,5-a]pyrimidine (dbtp), 5-methyl-7-isobutyl-1,2,4-triazolo[1,5-a]pyrimidine (ibmtp) or 5,7-diphenyl-1,2,4-triazolo[1,5-a]pyrimidine (dptp), whereas S-tetrahydrothio-phene-1-oxide (TMSO) or diphenyl sulfoxide (DPSO) were synthesized in a one-pot reaction. Here, we present experimental data (1H, 13C, 15N, 195Pt NMR, IR, X-ray) combined with density functional theory (DFT) computations to support and characterize structure–spectra relationships and determine the geometry of dichloride platinum(II) complexes with selected triazolopyrimidines and sulfoxides. Based on the experimental and theoretical data, factors affecting the stability of platinum(II) complexes have been determined.

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2

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.

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3

Badolato, Mariateresa, Fabrizio Manetti, Antonio Garofalo, and Francesca Aiello. "Triazolopyrimidinium salts: discovery of a new class of agents for cancer therapy." Future Medicinal Chemistry 12, no. 5 (March 2020): 387–402. http://dx.doi.org/10.4155/fmc-2019-0317.

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Aim: The [1,2,4]triazolo[1,5- a]pyrimidine core is highly privileged in medicinal chemistry due to its versatile pharmacological activity profile. Recently, the search for novel anticancer agents has focused on [1,2,4]triazolo[1,5- a]pyrimidine derivatives. Results: Our hit functionalization has led to the discovery of new [1,2,4]triazolo[1,5- a]pyrimidinium salts with potential anticancer activity. Among a small library of molecules, compound 9 significantly inhibits cancer cell growth in a panel of in vitro models. Molecular docking studies and preliminary binding assay have displayed that 9 could directly bind the Src homology 2 (SH2) domain of STAT3 protein. Conclusion: Compound 9 is a novel promising lead compound that motivates additional evaluation of [1,2,4]triazolo[1,5- a]pyrimidinium salts as novel potential chemotherapeutics.

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4

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.

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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.

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5

Argăseală, Aura, Cătălin Maxim, Mihaela Badea, Larisa Ioniță, Mariana Carmen Chifiriuc, Arpad Mihai Rostas, Mihaela Bacalum, et al. "Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands." Molecules 27, no. 3 (January 24, 2022): 765. http://dx.doi.org/10.3390/molecules27030765.

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In an attempt to increase the biological activity of the 1,2,4-triazolo[1,5-a]pyrimidine scaffold through complexation with essential metal ions, the complexes trans-[Cu(mptp)2Cl2] (1), [Zn(mptp)Cl2(DMSO)] (2) (mptp: 5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidine), [Cu2(dmtp)4Cl4]·2H2O (3) and [Zn(dmtp)2Cl2] (4) (dmtp: 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine), were synthesized and characterized as new antiproliferative and antimicrobial species. Both complexes (1) and (2) crystallize in the P21/n monoclinic space group, with the tetrahedral surroundings generating a square-planar stereochemistry in the Cu(II) complex and a tetrahedral stereochemistry in the Zn(II) species. The mononuclear units are interconnected in a supramolecular network through π–π interactions between the pyrimidine moiety and the phenyl ring in (1) while supramolecular chains resulting from C-H∙∙∙π interactions were observed in (2). All complexes exhibit an antiproliferative effect against B16 tumor cells and improved antibacterial and antifungal activities compared to the free ligands. Complex (3) displays the best antimicrobial activity against all four tested strains, both in the planktonic and biofilm-embedded states, which can be correlated to its stronger DNA-binding and nuclease-activity traits.

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6

Nassar, Ibrahim F., Mohammed T. Abdel Aal, Wael A. El-Sayed, Mahmoud A. E Shahin, Elsayed G. E. Elsakka, Mahmoud Mohamed Mokhtar, Maghawry Hegazy, Mohamed Hagras, Asmaa A. Mandour, and Nasser S. M. Ismail. "Discovery of pyrazolo[3,4-d]pyrimidine and pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives as novel CDK2 inhibitors: synthesis, biological and molecular modeling investigations." RSC Advances 12, no. 23 (2022): 14865–82. http://dx.doi.org/10.1039/d2ra01968j.

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A new set of pyrazolo[3,4-d]pyrimidine and pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine scaffolds (4–13) as well as the thioglycoside derivatives (14, 15) were designed, and synthesized as novel CDK2 targeting compounds.

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7

Fan, Ning-Juan, Yuan-feng Li, Shuang Liang, and Jiang-Jiang Tang. "Synthesis and cytotoxic activity of novel steroidal derivatives containing a [1,2,4]triazolo[1,5-a]pyrimidine ring." Journal of Chemical Research 41, no. 7 (July 2017): 413–15. http://dx.doi.org/10.3184/174751917x14967701767003.

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The synthesis of steroidal derivatives containing [1,2,4]triazolo[1,5- a]pyrimidine derived from progesterone is described. The Claisen condensations of Δ1,4-pregnadien-3,20-dione and 4-chloro-Δ1,4-pregnadien-3,20-dione with dimethyl oxalate afforded 21-methoxalylpregn-1,4-diene-3,20-dione and 4-chloro-21-methoxalylpregn-1,4-diene-3,20-dione, respectively. Furthermore, the reactions of these compounds with 3-amino-1,2,4-triazole yielded the corresponding [1,2,4]triazolo[1,5- a]pyrimidine derivatives. The newly synthesised compounds were evaluated in vitro by means of sulforhodamine B assays for antiproliferative activity against HeLa and MCF-7 cells.

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8

Łakomska, Iwona, Dariusz Śmiłowicz, Mateusz Jakubowski, Jerzy Sitkowski, and Andrzej Wojtczak. "Platinum(II) Complexes with Bulky Disubstitute Triazolopyrimidines as Promising Materials for Anticancer Agents." Materials 13, no. 23 (November 24, 2020): 5312. http://dx.doi.org/10.3390/ma13235312.

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Herein, we present dicarboxylate platinum(II) complexes of the general formula [Pt(mal)(DMSO)(L)] and [Pt(CBDC)(DMSO)(L)], where L is dbtp 5,7-ditertbutyl-1,2,4-triazolo[1,5-a]pyrimidine) or ibmtp (7-isobutyl-5-methyl-1,2,4- triazolo[1,5-a]pyrimidine), as prospective prodrugs. The platinum(II) complexes were synthesized in a one-pot reaction between cis-[PtCl2(DMSO)2], silver malonate or silver cyclobutane-1,1-dicarboxylate and triazolopyrimidines. All platinum(II) compounds were characterized by FT-IR, and 1H, 13C, 15N and 195Pt NMR; and their square planar geometries with one monodentate N(3)-bonded 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidine, one S-bonded molecule of dimethyl sulfoxide and one O,O-chelating malonato (1, 2) or O,O-chelating cyclobutane-1,1-dicarboxylato (3, 4) was determined. Additionally, [Pt(CBDC)(dbtp)(DMSO)] (3) exhibited (i) substantial in vitro cytotoxicity against the lung adenocarcinoma epithelial cell line (A549) (IC50 = 5.00 µM) and the cisplatin-resistant human ductal breast epithelial tumor cell line (T47D) (IC50 = 6.60 µM); and (ii) definitely exhibited low toxicity against normal murine embryonic fibroblast cells (BALB/3T3).

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9

Hossain, M. I., and M. M. H. Bhuiyan. "Synthesis and Antimicrobial Activities of Some New Thieno and Furopyrimidine Derivatives." Journal of Scientific Research 1, no. 2 (April 23, 2009): 317–25. http://dx.doi.org/10.3329/jsr.v1i2.2299.

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Fused pyrimidines, 8,9-dimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 5, 3,8,9-trimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 6, 4-benzylidinehydrazono-5,6 dimethylthieno[2,3-d]pyrimidine 7, 4-[4/-hydroxybenzylidine]hydrazono-5,6-dimethylthi-eno[2,3-d]pyrimidine 8, 4-[4/-tolylidin]hydrazono-5,6-dimethylthieno[2,3-d]pyrimidine 9, 4-[4/-nitrobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 10 and 4-[4/-chlorobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 11 are prepared in good yield by an initial treatment of 2-amino-4,5-dimethylthiophene-3-carbonitrile 1 with formic acid, affording 5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one 2, which is chlorinated with thionyl chloride and then hydrazinated with hydrazine hydrate. Finally hydrazino compound 4 is reacted with formic acid, acetic anhydrate, benzaldehyde, p-hydroxybenzaldehyde, p-toluayldehyde, p-nitrobenzaldehyde and p-chlorobenzaldehyde to give thienotriazolopyrimidines 5-6 and thienopyrimidines 7-11 respectively. All the compounds have been screened for their antimicrobial activity. Keywords: Fused pyrimidines; Hydrazino compound; Thienotriazolopyrmidines; Thienopyrimidines; Antimicrobial activity.© 2009 JSR Publications. ISSN: 2070-0237 (Print); 2070-0245 (Online). All rights reserved.DOI: 10.3329/jsr.v1i2.2299

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10

Tang, Caifei, Zhiming Li, and Quanrui Wang. "IBD-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent Dimroth rearrangement: Synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives." Beilstein Journal of Organic Chemistry 9 (November 25, 2013): 2629–34. http://dx.doi.org/10.3762/bjoc.9.298.

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Oxidative cyclization of 6-chloro-4-pyrimidinylhydrazones 4 with iodobenzene diacetate (IBD) in dichloromethane gives rise to [1,2,4]triazolo[4,3-c]pyrimidine derivatives 5a–o. These incipient products undergo feasible Dimroth rearrangement to furnish the isolated [1,2,4]triazolo[1,5-c]pyrimidines 6a–o in moderate to high yields.

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11

Hempel, Ute, Eberhard Lippmann, and Ernst Tenor. "1,2,4-Triazolo [1,5-a] pyrimidine, Darstellung 7-aminsubstituierter 6-Nitro-1,2,4-triazolo[1,5-a]-pyrimidine." Zeitschrift für Chemie 30, no. 5 (August 31, 2010): 170. http://dx.doi.org/10.1002/zfch.19900300505.

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12

Ahmed, Essam K., Johannes Fröhlich, and Fritz Sauter. "Fusion Reactions of N-Heterocyclic Moieties to Thiopyrano[4',3':4,5]thieno[2,3-d]pyrimidines." Collection of Czechoslovak Chemical Communications 61, no. 1 (1996): 147–54. http://dx.doi.org/10.1135/cccc19960147.

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Derivatives of the novel heterocyclic parent systems imidazolo[1,2-a]thiopyrano[4',3':4,5]thieno[2,3-d]pyrimidine (B) and thiopyrano[4',3':4,5]thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine (C) have been synthesized by fusing pyrimidine moieties to 2-amino-4,7-dihydro-5H-thieno[2,3-c]thiopyran-3-carboxylic acid ethyl ester (1) and -3-carbonitrile (10), followed by cyclization reactions of the title intermediates A thus obtained.

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13

Mounir, Salem, Magda Marzouk, and Naglaa Mahmoud. "Synthesis of various fused pyrimidine rings with their pharmacological and antimicrobial evaluation." Journal of the Serbian Chemical Society 79, no. 9 (2014): 1059–73. http://dx.doi.org/10.2298/jsc130528016m.

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Various fused pyrimidine such as furo[2,3-d]pyrimidine, triazolo[1,5-a]pyrimidine, tetrazolo[1,5-a]pyrimidine were synthesized from the reactions of thioxopyrimidine-6(1H)-ones with ethyl chloroacetate (under different reaction conditions), thiourea, and sodium nitrite. Pyrimidine thiones reacted with POCl3/PCl5 to give the chloro derivatives which reacted with sodium azide, and thiourea to give the tetrazolo[1,5-c]pyrimidine, pyrimido pyrimidine. Thioxopyrimidine-6(1H)-ones reacted with benzyl amine to give pyrrolo[2,3-d]pyrimidinethione. Theoretical calculation using MIDO/3, Fukui indices and the heat of formation of some compounds were carried out. The pharmacological and antimicrobial activities of some of the synthesized products were also evaluated.

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14

Yu, Guang-Xi, Ying Hu, Wei-Xin Zhang, Xin-Yi Tian, Sai-Yang Zhang, Yan Zhang, Shuo Yuan, and Jian Song. "Design, Synthesis and Biological Evaluation of [1,2,4]Triazolo[1,5-a]pyrimidine Indole Derivatives against Gastric Cancer Cells MGC-803 via the Suppression of ERK Signaling Pathway." Molecules 27, no. 15 (August 5, 2022): 4996. http://dx.doi.org/10.3390/molecules27154996.

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[1,2,4]Triazolo[1,5-a]pyrimidine and indole skeletons are widely used to design anticancer agents. Therefore, in this work, a series of [1,2,4]triazolo[1,5-a]pyrimidine indole derivatives were designed and synthesized by the molecular hybridization strategy. The antiproliferative activities of the target compounds H1–H18 against three human cancer cell lines, MGC-803, HCT-116 and MCF-7, were tested. Among them, compound H12 exhibited the most active antiproliferative activities against MGC-803, HCT-116 and MCF-7 cells, with IC50 values of 9.47, 9.58 and 13.1 μM, respectively, which were more potent than that of the positive drug 5-Fu. In addition, compound H12 could dose-dependently inhibit the growth and colony formation of MGC-803 cells. Compound H12 exhibited significant inhibitory effects on the ERK signaling pathway, resulting in the decreased phosphorylation levels of ERK1/2, c-Raf, MEK1/2 and AKT. Furthermore, compound 12 induced cell apoptosis and G2/M phase arrest, and regulated cell cycle-related and apoptosis-related proteins in MGC-803 cells. Taken together, we report here that [1,2,4]triazolo[1,5-a]pyrimidine indole derivatives, used as anticancer agents via the suppression of ERK signaling pathway and the most active compound, H12, might be a valuable hit compound for the development of anticancer agents.

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15

Salas, Juan M., Miguel Quirós, Mohammad Abul Haj, Rosa Magán, Clotilde Marín, Manuel Sáchez-Moreno, and René Faure. "Activity of Pt(II) and Ru(III) Triazolopyrimidine Complexes Against Parasites of the Genus Leishmania, Trypanosomas and Phytomonas." Metal-Based Drugs 8, no. 3 (January 1, 2001): 119–24. http://dx.doi.org/10.1155/mbd.2001.119.

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The synthesis and characterization of two Pt(II) Complexes with the isomeric ligands 4,5-dihydro-5-oxo- [1,2,4]triazolo-[ 1,5-a]pyrimidine (5HtpO) and 4,7-dihydro-7-oxo-[ 1,2,4]-triazolo-[ 1,5-a]pyrimidine (7HtpO) are described, as well as a Ru(III) complex with 7HtpO. The crystal structure of cis-[PtCl2(7HtpO)2].2H2O has been solved by X-ray diffraction analysis. In vitro activity of the new isolated complexes against the epimastigote form of T. cruzi, procyclic form of T. b. brucei and promastigote form of L. donnovani and P. characias has also been studied. The three complexes markedly affect the growth of the parasites and none of them shows cytotoxicity against macrophage of the J774.2 line at the heaviest dosages used.

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16

Abdel-Hafez, Shams H., Ragaa A. Ahmed, Mohamed A. Abdel-Azim, and Khairy M. Hassan. "Selenium containing Heterocycles: Part 1. Synthesis of Some New Substituted Pyrido[3′,2′:4,5]selenolo[3,2-d]pyrimidines and Related Fused Tetracyclic Systems." Journal of Chemical Research 2007, no. 10 (October 2007): 580–84. http://dx.doi.org/10.3184/030823407x25506.

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New series of selenolo[2,3- b]pyridine, pyrido[3′,2′:4,5]selenolo[3,2- d]pyrimidine, 7,8-dihydro-2,4-dimethylpyrrolo [1,2- a]pyrido[3′,2′:4,5]selenolo[3,2- d]pyrimidin-10(6 H)-one and 7,9-dimethylpyrido[3′,2′:4,5]selenolo[3,2- d][1,2,4] triazolo[4,3- c]pyrimidine derivatives were synthesised from 3-cyano-4,6-dimethylpyridine-2(1 H)-selenone (1). Spectroscopic (IR, 1H, MS) of the newly synthesised compounds are reported.

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17

Odabaşoğlu, Mustafa, and Orhan Büyükgüngör. "5,7-Dimethyl-1,2,4-triazolo[1,5-a]pyrimidine." Acta Crystallographica Section E Structure Reports Online 62, no. 4 (March 10, 2006): o1310—o1311. http://dx.doi.org/10.1107/s1600536806008166.

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The molecules in the title compound, C7H8N4, are linked into sheets by a combination of C—H...N hydrogen bonds and π–π interactions. The hydrogen bonds generate two-dimensional networks with a C(6) chain motif. There are two planar symmetry-independent molecules in the asymmetric unit, with a dihedral angle of 4.29 (8)° between their least-squares mean planes.

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18

Hempel, Ute, Eberhard Lippmann, and Ernst Tenor. "1,2,4-Triazolo [1,5-a] pyrimidine: Reaktionen von Amino-und Hydrazino-1,2,4-triazolo[1,5-a]pyrimidine mit Dimethylformamid-dimethylacetal." Zeitschrift für Chemie 30, no. 9 (August 31, 2010): 320–21. http://dx.doi.org/10.1002/zfch.19900300905.

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19

Biagi, Giuliana, Irene Giorgi, Oreste Livi, Federica Pacchini, and Valerio Scartoni. "New 1,2,3-triazolo[4,5-e]1,2,4-triazolo[4,3-c]pyrimidine derivatives II." Journal of Heterocyclic Chemistry 39, no. 5 (September 2002): 885–88. http://dx.doi.org/10.1002/jhet.5570390505.

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20

Ogorodnik, A. G., V. A. Yanchenko, L. S. Bobkova, N. M. Seredinska, and A. M. Demchenko. "Synthesis and anаlgеsic activity 5-methyl-3-aryl[1,2,4]triazolo[4,3-a]pyrimidin-7-oles derivatives." Farmatsevtychnyi zhurnal, no. 2 (August 14, 2018): 55–61. http://dx.doi.org/10.32352/0367-3057.2.17.07.

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Pain is a signal of inflammation and disruption of the body. It is the most important protective and adaptive mechanism that ensuring the safety of the individual. A strong and prolonged effect of "pain" irritant arising in injuries or after surgical manipulation transforms the protective reaction of the body to harmful factor that is the cause of secondary violations physiological processes. The aim of this work was the synthesis of substances in a series of 5-methyl-3-aryl [1,2,4] triazolo [4,3-a] pyrimidine-7-ol and study the analgesic effect of the synthesized compounds. The objects of our research were selected derivatives of 5-methyl-3-aryl [1,2,4] triazolo [4,3-a] pyrimidine-7-ol, which were synthesized by condensation and subsequent cyclization of 6-methyl-2-metylsulfanilpirymidyn-4-ol (1) with the corresponding substituted benzoic acid hydrazide The primary evaluation of analgesic activity conducted on thermal stimulation models («hot plate»). A number of 5-methyl-3-aryl [1,2,4] triazolo [4,3-a] pyrimidin-7-ol derivatives were synthesized, and their structure and purity were confirmed by 1H NMR spectroscopy. The analgesic activity of 5-methyl-3-aryl [1,2,4] triazolo [4,3-a] pyrimidin-7-ol was investigated in order to reveal the structure-activity relationship. The screening for analgesic activity for 5-methyl-3-aryl [1,2,4] triazolo [4,3-a] pyrimidin-7-ol derivatives in in vivo experiments on hot plate models showed that the highest activity Was noted for the compound containing the methyl group in the fourth position of the aryl substituent, which is 184.28% of the change in the latent period of the reaction, which exceeds the action of the reference preparation of ketorolac by 71.57%. The introduction of halogens into the aryl moiety leads to a decrease in the analgesic activity of the compounds. A series of 5-methyl-3-aryl [1,2,4] triazolo [4,3-a] pyrimidine-7-ol derivatives were synthesized by condensation and subsequent cyclization of 6-methyl-2-metylsulfanylpirymydyn-4-ol with relevant substituted hydrazide of benzoic acid. The structure and purity of obtained compounds were confirmed by 1H NMR spectroscopy. The analgesic activity of 5-methyl-3-aryl [1,2,4] triazolo [4,3-a] pyrimidin-7-ol was investigated in order to reveal the structure-activity relationship. The screening of analgesic activity of 5-methyl-3-aryl [1,2,4] triazolo [4,3-a] pirymidyn-7-ol derivatives in vivo models for «hot plate» shows that the highest activity was noted for compound containing methyl group in the fourth position of the aryl substituent, which is 184.28% change latent period reaction, that exceeds effect reference drug ketorolac at 71.57%. The introduction of halogens in the aryl fragment leads to a decrease analgesic activity of compounds.

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21

Abdelhamid, Abdou O., and Sobhi M. Gomha. "Synthesis of New Pyrazolo[1,5-a]pyrimidine, Triazolo[4,3-a]pyrimidine Derivatives, and Thieno[2,3-b]pyridine Derivatives from Sodium 3-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-3-oxoprop-1-en-1-olate." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/327095.

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Condensation of sodium 3-oxo-3-(1-phenyl-1H-pyrazol-4-yl)prop-1-en-1-olate (2) with several heterocyclic amines, cyanoacetamide, cyanothioacetamide, and 2-cyanoacetohydrazide gives pyrazolo[1,5-a]pyrimidines (5a–d), pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine (9), benzo[4,5]imidazo[1,2-a]pyrimidine (10), [1,2,4]triazolo[1,5-a]pyrimidine (11), and pyridine derivatives (12–14). Also, thieno[2,3-b]pyridines (15–18) were synthesized via pyridinethione (13) withα-halo ketones andα-halo ester. Structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data, alternative synthetic routes, and chemical transformation whenever possible.

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22

Łakomska, Iwona, Magdalena Babinska, Andrzej Wojtczak, Anna Kozakiewicz, Jerzy Sitkowski, and Andrzej A. Jarzęcki. "Experimental and theoretical investigation of the complexation of 5-methyl-7-isobutyl-1,2,4-triazolo[1,5-a]pyrimidine with platinum(ii) ions." New Journal of Chemistry 41, no. 15 (2017): 7775–82. http://dx.doi.org/10.1039/c7nj01112a.

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Dichlorido platinum(ii) complexes with 5-methyl-7-isobutyl-1,2,4-triazolo[1,5-a]pyrimidine (ibmtp) were synthesized and characterized by various tools: IR, ¹H, ¹³C, ¹⁵N, ¹⁹⁵Pt NMR and DFT calculations.

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23

Attanzio, Alessandro, Simone D’Agostino, Rosalia Busà, Anna Frazzitta, Simona Rubino, Maria Assunta Girasolo, Piera Sabatino, and Luisa Tesoriere. "Cytotoxic Activity of Organotin(IV) Derivatives with Triazolopyrimidine Containing Exocyclic Oxygen Atoms." Molecules 25, no. 4 (February 15, 2020): 859. http://dx.doi.org/10.3390/molecules25040859.

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In this study cytotoxicity of organotin(IV) compounds with 1,2,4-triazolo[1,5-a]pyrimidines, Me3Sn(5tpO) (1), n-Bu3Sn(5tpO) (2), Me3Sn(mtpO) (3), n-Bu3Sn(mtpO) (4), n-Bu3Sn(HtpO2) (5), Ph3Sn(HtpO2) (6) where 5HtpO = 4,5-dihydro-5-oxo-[1,2,4]triazolo-[1,5-a]pyrimidine, HmtpO = 4,7-dihydro-5-methyl-7-oxo-[1,2,4]triazolo-[1,5-a]pyrimidine, and H2tpO2 = 4,5,6,7-tetrahydro-5,7- dioxo-[1,2,4]triazolo-[1,5-a]-pyrimidine, was assessed on three different human tumor cell lines: HCT-116 (colorectal carcinoma), HepG2 (hepatocarcinoma) and MCF-7 (breast cancer). While 1 and 3 were inactive, compounds 2, 4, 5 and 6 inhibited the growth of the three tumor cell lines with IC50 values in the submicromolar range and showed high selectivity indexes towards the tumor cells (SI > 90). The mechanism of cell death triggered by the organotin(IV) derivatives, investigated on HCT-116 cells, was apoptotic, as evident from the externalization of phosphatidylserine to the cell surface, and occurred via the intrinsic pathway with fall of mitochondrial inner membrane potential and production of reactive oxygen species. While compound 6 arrested the cell progression in the G2/M cell cycle phase and increased p53 and p21 levels, compounds 2, 4 and 5 blocked cell duplication in the G1 phase without affecting the expression of either of the two tumor suppressor proteins. Compounds 1 and 2 were also investigated using single crystal X-ray diffraction and found to be, in both cases, coordination polymers forming 1 D chains based on metal-ligand interactions. Interestingly, for n-Bu3Sn(5tpO)(2) H-bonding interactions between 5tpO− ligands belonging to adjacent chains were also detected that resemble the “base-pairing” assembly and could be responsible for the higher biological activity compared to compound 1. In addition, they are the first example of bidentate N(3), O coordination for the 5HtpO ligand on two adjacent metal atoms.

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Shah, A. M., and A. J. Rojivadiya. "An Expeditious Synthesis of 1,2,4-Triazolo[1,5-a]Pyrimidine." International Letters of Chemistry, Physics and Astronomy 51 (May 2015): 1–4. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.51.1.

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A simple, efficient, and diversity oriented synthesis of library of 1,2,4-triazolo [1,5-a] pyrimidine was undertaken using 5-amino,1,2,4-triazole as a building block. The synthesized analogues were fully characterized by known spectroscopic techniques like FT-IR, 1H NMR, 13C NMR, and mass spectroscopy.

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25

Shah, A. M., and A. J. Rojivadiya. "An Expeditious Synthesis of 1,2,4-Triazolo[1,5-<i>a</i>]Pyrimidine." International Letters of Chemistry, Physics and Astronomy 51 (May 15, 2015): 1–4. http://dx.doi.org/10.56431/p-p4100a.

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A simple, efficient, and diversity oriented synthesis of library of 1,2,4-triazolo [1,5-a] pyrimidine was undertaken using 5-amino,1,2,4-triazole as a building block. The synthesized analogues were fully characterized by known spectroscopic techniques like FT-IR, 1H NMR, 13C NMR, and mass spectroscopy.

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26

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.

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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.

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27

Otero, Iran, Holger Feist, Dirk Michalik, Manfred Michalik, José Quincoces, and Klaus Peseke. "Synthesis of Iso-C-nucleoside Analogues from 1-(Methyl 2-O-benzyl-4,6- O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-ones." Zeitschrift für Naturforschung B 60, no. 11 (November 1, 2005): 1175–85. http://dx.doi.org/10.1515/znb-2005-1110.

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1-(Methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-one (3a) reacted with 3-amino-1H-1,2,4-triazole and 5-aminopyrazole-4-carboxylic acid derivatives in the presence of base to furnish the triazolo[1,5-a]pyrimidine (5) and the pyrazolo[1,5- a]pyrimidines (8a - d), respectively. Treatment of 1-(methyl 2-O-benzyl-4,6-O-benzylidene-3- deoxy-α-D-altropyranosid-3-yl)-4-phenyl-but-3-yn-2-one (3b) with cyanacetamide, 2-cyano-N- (4-methoxyphenyl)acetamide und N-aryl-3-oxo-butyramides afforded the substituted nicotinonitriles (11a - d). Furthermore, reaction of 3b with 2-benzimidazolyl-acetonitrile yielded the benz[4,5]imidazo[1,2-a]pyridine-4-carbonitrile (13). Deprotection of 8d in two steps afforded the 2-amino-N-benzyl-5-(methyl 3-deoxy-α-D-altropyranosid-3-yl-methyl)pyrazolo[1,5-a]pyrimidine- 3-carboxamide (10). Compounds 5 and 11d were treated with AcOH/H2O to furnish the 5-(methyl 2-O-benzyl-3-deoxy-α-D-altropyranosid-3-yl-methyl)[1,2,4]triazolo[1,5-a]pyrimidine (6) and the 3-acetyl-1,2-dihydro-1-(4-methoxyphenyl)-6-(methyl 2-O-benzyl-3-deoxy-α-D-altropyranosid-3-ylmethyl)- 4-phenylpyridin-2-one (12), respectively.

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28

MIYAMOTO, YOSHIKO. "Synthesis of (1,2,4)triazolo(1,5-c)pyrimidine derivatives." CHEMICAL & PHARMACEUTICAL BULLETIN 33, no. 7 (1985): 2678–87. http://dx.doi.org/10.1248/cpb.33.2678.

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29

Abarca, Belén, Rafael Ballesteros, Mimoun Chadlaoui, Javier Miralles, José Vicente Murillo, and Dimas Colonna. "The chemistry of [1,2,3]triazolo[1,5- c ]pyrimidine." Tetrahedron 57, no. 51 (December 2001): 10111–17. http://dx.doi.org/10.1016/s0040-4020(01)01053-5.

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30

Fizer, Maksym, and Mikhailo Slivka. "Synthesis of [1,2,4]triazolo[1,5-a]pyrimidine (microreview)." Chemistry of Heterocyclic Compounds 52, no. 3 (March 2016): 155–57. http://dx.doi.org/10.1007/s10593-016-1851-5.

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31

Chechina, Natal’ya V., Nadezhda N. Kolos, Irina V. Omelchenko, and Vladimir I. Musatov. "Synthesis of functionalized triazolo[1,5-a]pyrimidine derivatives." Chemistry of Heterocyclic Compounds 54, no. 1 (January 2018): 58–62. http://dx.doi.org/10.1007/s10593-018-2230-1.

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32

El Ashry, E. S. H., Y. El Kilany, N. Rashed, A. Mousaad, and H. Assafir. "Synthesis and Dimroth Rearrangement of 6-Cyano-l,2,4-triazolo- [4,3-a]pyrimidin-5- and 7-ones. A Novel Alkylation with Orthoesters and a New Participation of the Cyano Group in the Rearrangement." Zeitschrift für Naturforschung B 53, no. 10 (October 1, 1998): 1203–12. http://dx.doi.org/10.1515/znb-1998-1017.

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AbstractThe cyclization products of 5-cyano-2-hydrazino-6-phenyl-3,4-dihydropyrimidin-4-one (6) with one carbon inserting agents have been confirmed to be of the 1,2,4-triazolo[4,3-a]pyrimidin- 5(8H)-ones type and not the respective 7-ones, by comparing their alkylated derivatives 10a, 11a, 27 and 28 with the product from the cyclization of the 3-methyl and 3-benzyl derivatives of 6. A novel alkylation process was found when triethyl orthoformate was used as a cyclizing agent. Dimroth rearrangement of 8, 14, 15, 24, 34 and 36 with 2% ethanolic KOH gave the respective triazolo[1,5-a]pyrimidinone 13, 18, 19, 25, 38 and 40, respectively. Using 10% ethanolic KOH led to a novel participation of the cyano group in the rearrangement whereby 8a gave 7-imino-5-phenyl-l,2,4-triazolo[1,5-a]pyrimidine 22

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33

Swelam, Samira, Abd El-Salam, and Magdi Zaki. "Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives." Journal of the Serbian Chemical Society 64, no. 11 (1999): 655–62. http://dx.doi.org/10.2298/jsc9911655s.

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Reaction of 2 with different reagents, namely formic acid, acetic anhydride and trichloroacetonitrile, yielded pyrazolo[3,4-d]pyrimidine derivatives 3, 5 and 6, respectively. Pyrazolo[3,4-d]pyrimidine m-thiazine(7) and 2,4-(1H,3H)dithione (8) derivatives were formed by the action of carbon disulfide on 2, depending on the reaction medium. Interaction of 7 with hydrazine hydrate yielded the aminoimino derivative 9 which reacted with acetic anhydride, triethyl orthoacetate and/or appropriate aldehydes to give 11, 12 and 13a,b, respectively. Methylation of compound 8 gave 14, which reacted with hydrazine hydrate to afford the monohydrazino derivative 15. Reaction of 15, with formic acid and nitrous acid afforded pyrazolo[4,3-e]triazolo[1,5-c]pyrimidine (16) and pyrazolo[4,3-e]tetrazolo-[1,5-c]pyrimidine (17) derivatives, respectively. The structures of products 3-17 were identified in light of their elemental analyses and spectra data.

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34

Gami, Sagar P., Kalpesh V. Vilapara, Hasmukh R. Khunt, Jayesh S. Babariya, and Yogesh T. Naliapara. "Synthesis and Antimicrobal Activities of some Novel Triazolo[1,5-a]Pyrimidine Derivatives." International Letters of Chemistry, Physics and Astronomy 30 (March 2014): 127–34. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.30.127.

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A convenient synthesis of substituted 1,2,4-triazolo[1,5-a]pyrimidine was carried out by the reaction of various ketene dithioacetals with 5-amino 1,2,4-triazole in methanol in presence of sodium methoxide. The newly synthesized compound were characterized by 1H NMR, 13C NMR, IR, MS, elemental analysis and screened for their antimicrobial activity against various strains of bacteria and fungi.

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35

Gami, Sagar P., Kalpesh V. Vilapara, Hasmukh R. Khunt, Jayesh S. Babariya, and Yogesh T. Naliapara. "Synthesis and Antimicrobal Activities of some Novel Triazolo[1,5-a]Pyrimidine Derivatives." International Letters of Chemistry, Physics and Astronomy 30 (March 12, 2014): 127–34. http://dx.doi.org/10.56431/p-2r9pl7.

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A convenient synthesis of substituted 1,2,4-triazolo[1,5-a]pyrimidine was carried out by the reaction of various ketene dithioacetals with 5-amino 1,2,4-triazole in methanol in presence of sodium methoxide. The newly synthesized compound were characterized by 1H NMR, 13C NMR, IR, MS, elemental analysis and screened for their antimicrobial activity against various strains of bacteria and fungi.

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36

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.

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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.

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37

Surdykowski, A., E. Szłyk, and S. Larsen. "5,7-Diphenyl[1,2,4]triazolo[1,5-a]pyrimidine at 122K." Acta Crystallographica Section C Crystal Structure Communications 55, no. 8 (August 15, 1999): 1337–39. http://dx.doi.org/10.1107/s0108270199004631.

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38

Yavolovskii, A. A., E. I. Ivanov, A. V. Mazepa, and Yu E. Ivanov. "Synthesis of [1,2,3]Triazolo[4,5-d]pyrimidine 3-Oxides." Russian Journal of General Chemistry 73, no. 9 (September 2003): 1486–88. http://dx.doi.org/10.1023/b:rugc.0000016004.71832.bb.

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39

Fettouhi, M., A. Boukhari, B. El Otmani, and E. M. Essassi. "7-Ethoxycarbonylmethyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine." Acta Crystallographica Section C Crystal Structure Communications 52, no. 4 (April 15, 1996): 1031–32. http://dx.doi.org/10.1107/s0108270195013680.

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40

Salas, Juan M., M. Angustias Romero, M. Purificación Sánchez, and Miguel Quirós. "Metal complexes of [1,2,4]triazolo-[1,5-a]pyrimidine derivatives." Coordination Chemistry Reviews 193-195 (October 1999): 1119–42. http://dx.doi.org/10.1016/s0010-8545(99)00004-1.

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41

Hori, Mikio, Kiyomi Tanaka, Tadashi Kataoka, Hiroshi Shimizu, Eiji Imai, Kazuhiko Kimura, and Yoshinobu Hashimoto. "Thermolysis of [1,2,4]triazolo[1,5-a]pyrimidine n-ylides." Tetrahedron Letters 26, no. 10 (January 1985): 1321–22. http://dx.doi.org/10.1016/s0040-4039(00)94882-2.

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42

Rusinov, V. L., T. L. Pilicheva, and O. N. Chupakhin. "Synthesis of indolyl derivatives of triazolo[1,5-a]pyrimidine." Chemistry of Heterocyclic Compounds 21, no. 9 (September 1985): 1058. http://dx.doi.org/10.1007/bf00515036.

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43

Lokaj, Jan, Viktor Kettmann, Svetozár Katuščák, Petra Černuchová, Viktor Milata, and Fridrich Gregáň. "5-Methyl-1,2,4-triazolo[1,5-a]pyrimidine-6-carbonitrile." Acta Crystallographica Section E Structure Reports Online 62, no. 4 (March 8, 2006): o1252—o1253. http://dx.doi.org/10.1107/s1600536806007240.

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The title compound, C7H5N5, was designed and synthesized as a potential antitumour agent. The molecules are located on crystallographic mirror planes. The electron-accepting 6-cyano group has no effect on the π-electron cloud of the heterocyclic system. The molecular packing is governed by C—H...N intermolecular hydrogen bonds, which link the molecules into chains running along the c axis.

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44

Brazeau, Jean-Francois, and Gerard Rosse. "Triazolo[4,5-d]pyrimidine Derivatives as Inhibitors of GCN2." ACS Medicinal Chemistry Letters 5, no. 4 (February 12, 2014): 282–83. http://dx.doi.org/10.1021/ml500052f.

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45

Gründler, Peter, Waldemar Hofmann, and Gunther Fischer. "Die anodischen Polarogramme der symm.-Triazolo [1,5-a]pyrimidine." Zeitschrift für Chemie 14, no. 11 (September 1, 2010): 442. http://dx.doi.org/10.1002/zfch.19740141113.

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46

Jaenecke, Günter, Lieselotte Meister, Lisa Dressel, Renate Richter, and Harry Voigt. "Synthese substituierter 3H,5H-1,2,4-Triazolo[1,5-a]pyrimidine." Zeitschrift für Chemie 29, no. 10 (August 31, 2010): 378–79. http://dx.doi.org/10.1002/zfch.19890291005.

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47

Fischer, Gunther. "Synthese und Eigenschaften der s-Triazolo[1,5-a]pyrimidine." Zeitschrift für Chemie 30, no. 9 (August 31, 2010): 305–15. http://dx.doi.org/10.1002/zfch.19900300902.

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48

Shankar, Ravi B., and R. Garth Pews. "Synthesis of 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamides." Journal of Heterocyclic Chemistry 30, no. 1 (January 1993): 169–72. http://dx.doi.org/10.1002/jhet.5570300130.

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49

Kleschick, William A., Mark J. Costales, Joseph E. Dunbar, Richard W. Meikle, William T. Monte, Norman R. Pearson, Sigrid W. Snider, and Anna P. Vinogradoff. "New herbicidal derivatives of 1,2,4-triazolo [1,5-a] pyrimidine." Pesticide Science 29, no. 3 (1990): 341–55. http://dx.doi.org/10.1002/ps.2780290309.

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50

Dooley, Michael J., Ronald J. Quinn, Wyona C. Patalinghug, and Allan H. White. "Synthesis of a pyrimidine by elimination of nitrogen from a triazolo[4,5-d]pyrimidine." Tetrahedron Letters 31, no. 42 (January 1990): 6103–4. http://dx.doi.org/10.1016/s0040-4039(00)98041-9.

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