Synthesis of 5-amino-1,2,4-triazole-3-one through the nitroreduction of 5-nitro-1,2,4-triazole-3-one. Comparison between chemical and microbiological catalysis

Biocatalysis and Biotransformation

Volumn 17, Issue 1, 1999, Pages 37-44

  Le Campion, Laurence ^a   Ouazzani, Jamal ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

Bacillus licheniformis; Biotransformation; Nitroreduction; Nitrotriazolone; Penicillium sp.

Indexed keywords

AMINES; AROMATIC COMPOUNDS; CARBON; CATALYSIS; CATALYSTS; FUNGI; HYDROGENATION; METHANOL; MICROORGANISMS; PALLADIUM; REDUCTION;

BIOTRANSFORMATION; NITROREDUCTION; NITROTRIAZOLE;

BIOSYNTHESIS;

AMINE; AMINOTRIAZOLE; CARBON; METHANOL; PALLADIUM;

AQUEOUS SOLUTION; ARTICLE; BACILLUS LICHENIFORMIS; BIOTRANSFORMATION; CATALYSIS; CHEMICAL REACTION; COMPARATIVE STUDY; HYDROGENATION; INDUSTRIAL WASTE; MICROBIOLOGY; MICROORGANISM; NONHUMAN; REDUCTION; SYNTHESIS;

EID: 0032896217     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.3109/10242429909003205     Document Type: Article

References (30)

1. Aguilar, E.G., De Abranz, C.K., De Toranzo, E.G.D. and Castro, J.A. (1985) Benznidazole and nifurtimox nitroreductase activity in liver microsomes from male rats preinduced with phenobarbital or 3-methylcholanthrene. Res. Commun. Chem. Parhol. Pharmacol., 50, 443-446.
2. Al Shaar, A.H.M., Gilmour, D.W., Lythgoe, D.J., McClenaghan, I. and Ramsden, C.A. (1992) Preparation, structure and addition reactions of 4- and 5-nitroimidazoles. J. Chem. Soc. Perkin Trans I, 2779-2788.
3. Becuwe, A. and Delclos, A. (1993) Low-sensitivity explosive compounds for low vulnerability warheads. Propellants, Explosives, Pyrotechnies, 18, 1-10.
4. Bellamy, F.D. and Ou, K. (1984) Selective reduction of aromatic nitro compounds with stannous chloride in non acidic and non aqueous medium. Tetrahedron Letters, 25(8), 839-842.
5. Buehler, C.A. and Pearson, D.A. (1970) In "Survey of Organic Syntheses". Interscience: New York, N.Y.
6. Chipen, G.I., Bokalder, R.P. and Grinshtein, V.Ya. (1966) 1,2,4-triazol-3-one and its nitro and amino derivatives. Khimiya Geterotsiklicheskikh Soedinenii, 2(1), 110-116.
7. Djuric, Z. (1989) Reductive metabolism and DNA binding of misonodazole. Toxicol. Appl. Pharmacol., 101, 47-54.
8. Ehlhardt, W.J., Beaulieu, B.B. and Goldman, P. Jr. (1987) Formation of an amino reduction product of metronidazole in bacterial cultures: lack of bactericidal activity. Biochem. Pharmacol., 36(2), 259-264.
9. Farah, S.F. and McClelland, R.A. (1992) Preparation and reactions of bromo-2-nitro- and bromo-2-aminoimidazoles. Can. J. Chem., 71, 427-432.
10. Feller, D.R., Morita, M. and Gillette, J.R. (1971) Enzymatic reduction of niridazole by rat liver microsomes. Biochem. Pharmacol., 20, 203-215.
11. Godfrey, L.E.A. and Kurzer, F. (1960) Heterocyclic compounds from urea derivatives. Part I. A new synthesis of 3-amino-5-mercapto (and -hydroxy)-1,2,4-triazoles. J. Chem. Soc., 3437-3444.
12. Griffin, R.J., Meek, M.A., Schwalbe, C.H. and Stevens, M.F.G. (1989) Structural studies on bioactive compounds. 8. Synthesis, Crystal structure, and biological properties of a new series of 2,4-diamino-5-aryl-6-ethylpyrimidine dihydrofolate reductase inhibitors with in vivo activity against a methotrexate-resistant tumor cell line. J. Med. Chem., 32, 2468-2474.
13. Hanaya, K., Muramatsu, T., Kudo, H. and Chow, Y.L. (1979) Reduction of aromatic nitro-compounds to amines with sodium borohydride-copper(II) acetylacetonate. J. Chem. Soc. Perkin I, 2409-2410.
14. Iwata, N., Fukuhara, K., Suzuki, K., Miyata, N. and Takahashi, A. (1992) Reduction properties of nitrated naphthalenes: relationship between electrochemical reduction potential and the enzymatic reduction by microsomes or cytosol from rat liver. Chem. Biol. Interact., 85, 187-197.
15. Manchot, W. and Noll, R. (1905) Liehigs Ann. Chem., 343, 1.
16. Manning, B.W., Campbell, W.L., Franklin, W., Delclos, K.B. and Cerniglia, C.E. (1988) Metabolism of 6-nitrochrysene by intestinal microflora. Appl. Environ. Microbiol., 54(1), 197-203.
17. Marvin-Sikkema, F.D. and de Bont, J.A.M. (1994) Degradation of nitroaromatic compounds by microorganisms. Appl. Microbiol. Biotechnol., 42, 499-507.
18. 2 inhibition of nitroreductase. Biochem. Biophys. Res. Commun., 67(4), 1267-1274.
19. Michael, J., Larson, S.B., Vaghefi, M.M. and Robins, R.K. (1990) Synthesis of certain 1,2,5-triazole nucleoside derivatives. J. Heterocyclic Chem., 27, 1063-1071.
20. Osby, J.O. and Ganem, B. (1985) Rapid and efficient of aliphatic nitro compounds to amines. Tetrahedron Letters, 26(52), 6413-6416.
21. Petrini, M., Ballini, R. and Rosini, G. (1987) Reduction of aliphatic and aromatic compounds with sodium borohydride in tetrahydrofuran using 10% palladium-on-carbon as catalyst. Synthesis, 8, 713-714.
22. Pevzner, M.S., Kulibabina, T.N., Povarova, N.A. and Kilina, L.V. (1979) Heterocyclic nitro compounds. Nitration of 5-amino-1,2,4-triazole and 5-acetamido-1,2,4-triazole with acetyl nitrate and nitronium salts. Khim. Geterotsikl. Soedin., 8, 1132-1135.
23. Ram, S. and EhrenKaufer, R.E. (1984) A general procedure for mild and rapid reduction of aliphatic nitro compounds using ammonium formate as a catalytic hydrogen transfer agent. Tetrahedron Letters, 25(32), 3415-3418.
24. Rampulla, R.A. and Russell, R.K. (1986) Selective reduction of nitroarylhydrazones by catalytic transfer hydrogenation with cyclohexene. Synthetic Communications, 16(10), 1229-1232.
25. Sudarsanam, V., Nagarajan, K. and Gokhale, N.G. (1982) Nitroimidazoles: PART XVII-5-aminoimidazoles. Indian J. Chem., 21B, 1087-1091.
26. Sullivan, C.E., Tally, P.P., Goldin, B.R. and Vouros, P. (1982) Synthesis of 1-(2-hydroxyelhyl)-2-methyl-5-aminoimidazole: a ring-intact reduction product of metronidazole. Biochem. Pharmacol., 31(16), 2689-2691.
27. Walton, M.I. and Workman, P. (1987) Nitroimidazole bioreductive metabolism - Quantitation and characterisation of mouse tissue benznidazole nitroreductases in vivo and in vitro. Biochem. Pharmacol., 36(6), 887-896.
28. Walton, M.I., Blechen, N.M. and Workman, P. (1987) Heat-stimulated nitroreductive bioactivation of the 2-nitroimidazole benznidazole in vitro. Biochem. Pharmacol., 36, 2627-2632.
29. Wardman, P. and Clarke, E.D. (1976) Oxygen inhibilion of nitroreductase: electron transfer from nitro radical-anions to oxygen. Biochem. Biophys. Res. Commun., 69, 942-949.
30. Wheeler, L.A., Soderberg, F.B. and Goldman, P. (1975) The relationship between nitro group reduction and the intestinal microflora. J. Pharmacol. Exp. Tiler., 194, 135-144.