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Chemical Compound Review

Pyrrodiazole     1H-1,2,4-triazole

Synonyms: s-Triazole, PubChem17626, CHEMBL15571, SureCN18296, SureCN27820, ...
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Disease relevance of 288-89-1


High impact information on 288-89-1

  • The specific activity of catalase in the BAL fluids of animals given 3-amino, 1,2,4 triazole (AT) 1 h before lavaging showed drops from 0.97 in untreated monkeys to 0.04 in FNLP-treated and 0.49 in PMA-treated monkeys [6].
  • Two 1,2,4-triazole-resistant strains bearing mutations in cysK, the structural gene for O-acetylserine sulfhydrylase A, incorporate only small quantities of O-acetyl-L-serine into 1,2,4-triazole-1-alanine in vivo [1].
  • The X-ray crystal structure of the complex between human carbonic anhydrase II and the inhibitor 1,2,4-triazole has been refined at 1.9 A resolution to a final R-factor of 0.153 [7].
  • We report the computer-aided design, chemical synthesis, and biological evaluation of a novel family of delta opioid receptor (DOR) antagonists containing a 1,2,4-triazole core structure that are structurally distinct from other known opioid receptor active ligands [8].
  • To evaluate the possibility of introducing azole nucleosides as building blocks for metal-mediated base pairs in artificial oligonucleotides, imidazole nucleoside, 1,2,4-triazole nucleoside and tetrazole nucleoside have been synthesized and characterized [9].

Chemical compound and disease context of 288-89-1


Biological context of 288-89-1


Anatomical context of 288-89-1


Associations of 288-89-1 with other chemical compounds


Gene context of 288-89-1

  • CysK and cysB mutants showed cross-resistance to azide and 1,2,4-triazole [24].
  • A new class of regulatory mutants in the cysB locus has been isolated by plating cysM strains, under anaerobic conditions, on medium containing 1,2,4-triazole [25].
  • Synthesis and some first-row transition-metal complexes of the 1,2,4-triazole-based Bis(terdentate) ligands TsPMAT and PMAT [26].
  • The inhibitor was identified as catalase based upon its elution from the columns and removal with 3-amino- 1,2,4-triazole (AT), a catalase inhibitor [27].
  • s-triazole systems. Part IV: Novel substituted thio-s-triazole derivatives [28].


  1. Studies on the mechanism of inhibition of Salmonella typhimurium by 1,2,4-triazole. Kredich, N.M., Foote, L.J., Hulanicka, M.D. J. Biol. Chem. (1975) [Pubmed]
  2. The 1.15A crystal structure of the Staphylococcus aureus methionyl-aminopeptidase and complexes with triazole based inhibitors. Oefner, C., Douangamath, A., D'Arcy, A., Häfeli, S., Mareque, D., Mac Sweeney, A., Padilla, J., Pierau, S., Schulz, H., Thormann, M., Wadman, S., Dale, G.E. J. Mol. Biol. (2003) [Pubmed]
  3. Occurrence of 1,2,4-triazole ring in actinomycetes. Imamura, N., Murata, M., Yao, T., Oiwa, R., Tanaka, H., Omura, S. J. Antibiot. (1985) [Pubmed]
  4. Selective inhibition of virus multiplication by new acylated 1,2,4-triazole derivatives. Horváth, S., Somorai, T., Szilágyi, G. Antiviral Res. (1986) [Pubmed]
  5. A comparison of some effects of phosphine, hydrogen cyanide and anoxia in the lesser grain borer, Rhyzopertha dominica (F.) (Coleoptera: Bostrychidae). Price, N.R., Walter, C.M. Comp. Biochem. Physiol. C, Comp. Pharmacol. Toxicol. (1987) [Pubmed]
  6. Experimental pulmonary inflammatory injury in the monkey. Revak, S.D., Rice, C.L., Schraufstätter, I.U., Halsey, W.A., Bohl, B.P., Clancy, R.M., Cochrane, C.G. J. Clin. Invest. (1985) [Pubmed]
  7. Crystal structure of the complex between human carbonic anhydrase II and the aromatic inhibitor 1,2,4-triazole. Mangani, S., Liljas, A. J. Mol. Biol. (1993) [Pubmed]
  8. Discovery of novel triazole-based opioid receptor antagonists. Zhang, Q., Keenan, S.M., Peng, Y., Nair, A.C., Yu, S.J., Howells, R.D., Welsh, W.J. J. Med. Chem. (2006) [Pubmed]
  9. Metal ion coordination to azole nucleosides. Müller, J., Böhme, D., Lax, P., Morell Cerdà, M., Roitzsch, M. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
  10. Genetic instability in auxotrophs of Salmonella typhimurium requiring cysteine or methionine and resistant to inhibition by 1,2,4-triazole. Kingsman, A.J., Smith, D.A., Hulanicka, M.D. Genetics (1978) [Pubmed]
  11. Solid-phase synthesis of 5-amino-1-(substituted thiocarbamoyl)pyrazole and 1,2,4-triazole derivatives via dithiocarbazate linker. Hwang, J.Y., Choi, H.S., Lee, D.H., Yoo, S.E., Gong, Y.D. Journal of combinatorial chemistry. (2005) [Pubmed]
  12. Synthesis and serotonergic activity of N,N-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine and analogues: potent agonists for 5-HT1D receptors. Street, L.J., Baker, R., Davey, W.B., Guiblin, A.R., Jelley, R.A., Reeve, A.J., Routledge, H., Sternfeld, F., Watt, A.P., Beer, M.S. J. Med. Chem. (1995) [Pubmed]
  13. Interaction of the unique competitive inhibitor imidazole and related compounds with the active site metal of carbonic anhydrase: linkage between pH effects on the inhibitor binding affinity and pH effects on the visible spectra of inhibitor complexes with the cobalt-substituted enzyme. Khalifah, R.G., Rogers, J.I., Mukherjee, J. Biochemistry (1987) [Pubmed]
  14. A comparative study of 1-substituted imidazole and 1,2,4-triazole antifungal compounds as inhibitors of testosterone hydroxylations catalysed by mouse hepatic microsomal cytochromes P-450. Ballard, S.A., Lodola, A., Tarbit, M.H. Biochem. Pharmacol. (1988) [Pubmed]
  15. Determination of 22 triazole compounds including parent fungicides and metabolites in apples, peaches, flour, and water by liquid chromatography/tandem mass spectrometry. Schermerhorn, P.G., Golden, P.E., Krynitsky, A.J., Leimkuehler, W.M. Journal of AOAC International. (2005) [Pubmed]
  16. Monocyclic L-nucleosides with type 1 cytokine-inducing activity. Ramasamy, K.S., Tam, R.C., Bard, J., Averett, D.R. J. Med. Chem. (2000) [Pubmed]
  17. Cytochemical localization of catalase activity in methanol-grown Hansenula polymorpha. van Dijken, J.P., Veenhuis, M., Vermeulen, C.A., Harder, W. Arch. Microbiol. (1975) [Pubmed]
  18. Effect of 3 amino 1,2,4 triazole administration on the early CCl4-induced ultrastructural alterations in rat liver. Bernacchi, A.S., de Castro, C.R., de Ferreyra, E.C., de Fenos, O.M., Castro, J.A. British journal of experimental pathology. (1982) [Pubmed]
  19. 1,3,4-Oxadiazole, 1,3,4-thiadiazole, and 1,2,4-triazole analogs of the fenamates: in vitro inhibition of cyclooxygenase and 5-lipoxygenase activities. Boschelli, D.H., Connor, D.T., Bornemeier, D.A., Dyer, R.D., Kennedy, J.A., Kuipers, P.J., Okonkwo, G.C., Schrier, D.J., Wright, C.D. J. Med. Chem. (1993) [Pubmed]
  20. Quantitative polyphosphate-induced "prebiotic" peptide formation in H2O by addition of certain azoles and ions. Rabinowitz, J., Hampaï, A. J. Mol. Evol. (1984) [Pubmed]
  21. Design of 5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-thiadiazoles, -1,3,4-oxadiazoles, and -1,2,4-triazoles as orally-active, nonulcerogenic antiinflammatory agents. Mullican, M.D., Wilson, M.W., Connor, D.T., Kostlan, C.R., Schrier, D.J., Dyer, R.D. J. Med. Chem. (1993) [Pubmed]
  22. Rapid liquid chromatographic determination of residual penicillin G in milk. Furusawa, N. Fresenius' journal of analytical chemistry. (2000) [Pubmed]
  23. Taurine modulates catalase, aldehyde dehydrogenase, and ethanol elimination rates in rat brain. Ward, R.J., Kest, W., Bruyeer, P., Lallemand, F., De Witte P, n.u.l.l. Alcohol Alcohol. (2001) [Pubmed]
  24. Interference of azide with cysteine biosynthesis in Salmonella typhimurium. Filutowicz, M., Cieśla, Z., Kłopotowski, T. J. Gen. Microbiol. (1979) [Pubmed]
  25. A new class of mutants of the cysB regulatory gene for cysteine biosynthesis in Salmonella typhimurium. Wiater, A., Filutowicz, M., Hulanicka, D. J. Gen. Microbiol. (1982) [Pubmed]
  26. Synthesis and some first-row transition-metal complexes of the 1,2,4-triazole-based Bis(terdentate) ligands TsPMAT and PMAT. Klingele, M.H., Moubaraki, B., Murray, K.S., Brooker, S. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
  27. The determination of myeloperoxidase activity in liver. Duval, D.L., Howard, D., McCalden, T.A., Billings, R.E. Life Sci. (1990) [Pubmed]
  28. s-triazole systems. Part IV: Novel substituted thio-s-triazole derivatives. Awad, I.M., Bakhite, E.A., Abdel-Rahman, A.E. Journal of chemical technology and biotechnology (Oxford, Oxfordshire : 1986) (1992) [Pubmed]
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