l-Proline-catalysed facile green protocol for the synthesis and antimycobacterial evaluation of [1,4]-thiazines

European Journal of Medicinal Chemistry

Volumn 44, Issue 12, 2009, Pages 4978-4984

  Indumathi, Sethuraman ^a   Perumal, Subbu ^a   Banerjee, Debjani ^b   Yogeeswari, Perumal ^b   Sriram, Dharmarajan ^b  

^a MADURAI KAMARAJ UNIVERSITY   (India)

^b BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

Author keywords

Antimycobacterial activity; l Proline; Multi drug resistant tuberculosis; Mycobacterium smegmatis; Mycobacterium tuberculosis; Thiazine; Tuberculosis

Indexed keywords

ANTIMYCOBACTERIAL AGENT; ETHYL 3,5 DI(2 BROMOPHENYL) 6 (4 CHLOROBENZOYL) 4 METHYL 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 4 BENZYL 6 (4 CHLOROBENZOYL) 1,1 DIOXO 3,5 DIPHENYL 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 4 BENZYL 6 (4 CHLOROBENZOYL) 3,5 DI(3 FLUOROPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 4 BENZYL 6 (4 CHLOROBENZOYL) 3,5 DI(4 CHLOROPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 4 BENZYL 6 (4 CHLOROBENZOYL) 3,5 DI(4 FLUOROPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 4 BENZYL 6 (4 CHLOROBENZOYL) 3,5 DI(4 METHOXYLPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 4 BENZYL 6 (4 CHLOROBENZOYL) 3,5 DI(4 METHYLPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 1,1 DIOXO 3,5 DI(2 THIENYL) 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 1,1 DIOXO 3,5 DIPHENYL 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 3,5 DI(1 NAPHTHYL) 1,1 DIOXO 1M4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 3,5 DI(2 FURYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 3,5 DI(2 FURYL) 4 METHYL 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 3,5 DI(2 METHOXYPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 3,5 DI(2 NITROPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 3,5 DI(2,4 DICHLOROPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 3,5 DI(3 FLUOROPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 3,5 DI(3 NITROPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 3,5 DI(4 CHLOROPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 3,5 DI(4 CHLOROPHENYL) 4 METHYL 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 3,5 DI(4 METHOXYPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 3,5 DI(4 NITROPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 3,5 DI[4 (DIMETHYLAMINO)PHENYL] 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 4 METHYL 1,1 DIOXO 3,5 DIPHENYL 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 4 METHYL 3,5 DI(2 METHYLPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 4 METHYL 3,5 DI(3 NITROPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ETHYL 6 (4 CHLOROBENZOYL) 4 METHYL 3,5 DI(4 METHYLPHENYL) 1,1 DIOXO 1,4 THIAZINANE 2 CARBOXYLATE; ISONIAZID; RIFAMPICIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AGAR DILUTION; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; BACTERIUM CULTURE; CATALYST; CHEMICAL REACTION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MULTIDRUG RESISTANCE; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; SUBSTITUTION REACTION;

ANTI-BACTERIAL AGENTS; ANTITUBERCULAR AGENTS; CATALYSIS; DRUG RESISTANCE, MULTIPLE, BACTERIAL; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; PROLINE; THIAZINES;

EID: 70449631071     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.09.001     Document Type: Article

References (24)

1. de Souza M.V.N. Recent Pat. Anti-infect. Drug Discov. 1 (2006) 33-44
2. de Souza M.V.N. Curr. Opin. Pulm. Med. 12 (2006) 167-171
3. http://www.who.int/tdr/diseases/tb/default.htm
4. Honer zu Bentrup K., and Russell D.G. Trends Microbiol. 9 (2001) 597-605
5. Agerton T.B., Valway S.E., Blinkhorn R.J., Shilkret K.L., Reves R., Schluter W.W., Gore B., Pozsik C.J., Plikaytis B.B., Woodley C., and Onorato I.M. Clin. Infect. Dis. 29 (1999) 85-92
6. Dye C., Williams B.G., Espinal M.A., and Raviglione M.C. Science 295 (2002) 2042-2046
7. Ranjith Kumar R., Perumal S., Senthilkumar P., Yogeeswari P., and Sriram D. Bioorg. Med. Chem. Lett. 17 (2007) 6459-6462
8. Ranjith Kumar R., Perumal S., Senthilkumar P., Yogeeswari P., and Sriram D. Tetrahedron 64 (2008) 2962-2971
9. Ranjith Kumar R., Perumal S., Senthilkumar P., Yogeeswari P., and Sriram D. Eur. J. Med. Chem. 44 (2009) 3821-3829
10. Ranjith Kumar R., Perumal S., Senthilkumar P., Yogeeswari P., and Sriram D. J. Med. Chem. 51 (2008) 5731-5735
11. Karthikeyan S.V., Perumal S., Krithika A.S., Yogeeswari P., and Sriram D. Bioorg. Med. Chem. Lett. 19 (2009) 3006-3009
12. K. Balamurugan, S. Perumal, A. Sunil Kumar Reddy, P. Yogeeswari, D. Sriram, Tetrahedron Lett., in press.
13. Alcaide B., Almendros P., Luna A., and Torres M.R. J. Org. Chem. 71 (2006) 4818-4822
14. Janey J.M., Hsiao Y., and Armstrong III J.D. J. Org. Chem. 71 (2006) 390-392
15. Kotrusz P., and Toma S. Molecules 11 (2006) 197-205
16. Chen H., Wang Y., Wei S., and Sun J. Tetrahedron: Asymmetry 18 (2007) 1308-1312
17. Ramachary D.B., Chowdari N.S., and Barbas III C.F. Angew. Chem. 115 (2003) 4365-4369
18. Kim I., Kim S.G., Choi J., and Lee G.H. Tetrahedron 64 (2008) 664-671
19. Yadav J.S., Kumar S.P., Kondaji G., Rao R.S., and Nagaiah K. Chem. Lett. 33 (2004) 1168-1169
20. Mabry J., and Ganem B. Tetrahedron Lett. 47 (2006) 55-56
21. Srinivasan M., and Perumal S. Tetrahedron 63 (2007) 2865-2874
22. S. Indumathi, S. Perumal, Unpublished results.
23. Reddy D.B., Reddy M.M., and Reddy P.V.R. Indian J. Chem. 32B (1993) 1018-1023
24. Sriram D., Yogeeswari P., Dinakaran M., and Thirumurugan R. J. Antimicrob. Chemother. 59 (2007) 1194-1196