Anti-tubercular agents. Part 5: Synthesis and biological evaluation of benzothiadiazine 1,1-dioxide based congeners

European Journal of Medicinal Chemistry

Volumn 45, Issue 10, 2010, Pages 4545-4553

  Kamal, Ahmed ^a   Shetti, Rajesh V C R N C ^a   Azeeza, Shaik ^a   Ahmed, S Kaleem ^a   Swapna, P ^a   Reddy, A Malla ^a   Khan, Inshad Ali ^b   Sharma, Sandeep ^b   Abdullah, Sheikh Tasduq ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

Author keywords

Anti tubercular agents; Benzothiadiazine 1,1 dioxides; M. tuberculosis; MDR and XDR TB

Indexed keywords

2,3 DIHYDRO 2 METHYL 6 NITRO 2 [4 [4 (4 TRIFLUOROMETHOXYPHENOXY) 1 PIPERIDINYL]PHENOXYMETHYL]IMIDAZO[2,1 B]OXAZOLE; 3 (N BOC PIPERAZINYL) 4 PHENYL 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 (N ISONIPICOTINIC METHYL ESTER) 4 ETHYL 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 (N ISONIPICOTINIC METHYL ESTER) 4 METHYL 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 (N ISONIPICOTINIC METHYL ESTER) 4 PHENYL 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 [4 [(5 NITRO 2 FURYL)CARBONYL]PIPERAINYL] 4 ETHYL 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 [4 [(5 NITRO 2 FURYL)CARBONYL]PIPERAINYL] 4 METHYL 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 [4 [(5 NITRO 2 FURYL)CARBONYL]PIPERAINYL] 4 PHENYL 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 [4 [(5 NITRO 2 FURYL)METHYL]PIPERAZINYL] 4 ETHYL 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 [4 [(5 NITRO 2 FURYL)METHYL]PIPERAZINYL] 4 METHYL 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 [4 [(5 NITRO 2 FURYL)METHYL]PIPERAZINYL] 4 PHENYL 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 [4 [(5 NITRO 2 THIENYL)METHYL]PIPERAZINYL] 4 ETHYL 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 [4 [(5 NITRO 2 THIENYL)METHYL]PIPERAZINYL] 4 METHYL 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 [4 [(5 NITRO 2 THIENYL)METHYL]PIPERAZINYL] 4 PHENYL 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 6,7 DIHYDRO 2 NITRO 6 (4 TRIFLUOROMETHOXYBENZYLOXY) 5H IMIDAZO[2,1 B][1,3]OXAZINE; AMPHOTERICIN; BENZOTHIADIAZINE 1,1 DIOXIDE; CIPROFLOXACIN; N 4 [1 (5 NITRO 2 FURYL)METHYLIDENE] 1 (4 ETHYL 1,1 DIOXO 1,4 DIHYDRO1,2,4 BENZOTHIADAZIN 3 YL) 4 PIPERDIN CARBOHYDRAZIDE; N 4 [1 (5 NITRO 2 FURYL)METHYLIDENE] 1 (4 METHYL 1,1 DIOXO 1,4 DIHYDRO1,2,4 BENZOTHIADAZIN 3 YL) 4 PIPERDIN CARBOHYDRAZIDE; N 4 [1 (5 NITRO 2 FURYL)METHYLIDENE] 1 (4 PHENYL 1,1 DIOXO 1,4 DIHYDRO1,2,4 BENZOTHIADAZIN 3 YL) 4 PIPERDIN CARBOHYDRAZIDE; RIFAMPICIN; STREPTOMYCIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; IN VIVO STUDY; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; TUBERCULOSIS;

ANIMALS; ANTITUBERCULAR AGENTS; BACTERIA; BENZOTHIADIAZINES; CELL LINE; CELL SURVIVAL; FEMALE; FUNGI; HUMANS; MICE; MICE, INBRED BALB C; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; TUBERCULOSIS;

EID: 77956189502     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.07.015     Document Type: Article

References (29)

1. J. Boogaard, G.S. Kibiki, E.R. Kisanga, M.J. Boeree, and R.E. Aarnoutse Antimicrob. Agents Chemother. 53 2009 849 862
2. World Health Organization Tuberculosis Facts 2008 http://www.who.int/tb
3. C. Dye Nat. Rev. Microbiol. 7 2009 81 87
4. A.M. Ginsberg Semin. Respir. Crit. Care Med. 29 2008 552 559
5. H. Tomioka, Y. Tatano, K. Yasumoto, and T. Shimizu Expert ReV. Resp. Med. 2 2008 455 471
6. D.A. Mitchison Am. J. Resp. Crit. Care Med. 171 2005 699 706
7. V. Claire, C. Nicholas, A. David, D. Vincent, R.B. Alain, and F.D. Yves Langmuir 25 2009 4324 4327
8. D. Chatterjee Curr. Opin. Chem. Biol. 1 1997 579 588
9. D. Alsteens, C. Verbelen, E. Dague, D. Raze, A. Baulard, and Y.F. Dufrene Pflug. Arch. Eur. J. Phys. 456 2008 117 125
10. A. Banerjee, E. Dubnau, A. Quemard, V. Balasubramanian, K.S. Um, T. Wilson, D. Collins, G. Delisle, and W.R. Jacobs Science 263 1994 227 230
11. A. Kamal, A.H. Babu, A.V. Ramana, R. Sinha, J.S. Yadav, and S.K. Arora Bioorg. Med. Chem. Lett. 15 2005 1923 1926
12. A. Kamal, A.A. Shaik, R. Sinha, J.S. Yadav, and S.K. Arora Bioorg. Med. Chem. Lett. 15 2005 1927 1929
13. A. Kamal, K.S. Reddy, S.K. Ahmed, M.N.A. Khan, R.K. Sinha, J.S. Yadav, and S.K. Arora Bioorg. Med. Chem. 14 2006 650 658
14. A. Kamal, S.K. Ahmed, K.S. Reddy, M.N.A. Khan, R.V.C.R.N.C. Shetti, B. Siddhardha, U.S.N. Murthy, I.A. Khan, M. Kumar, S. Sharma, and A.B. Ram Bioorg. Med. Chem. Lett. 17 2007 5419 5422
15. A. Kamal, S. Azeeza, M.S. Malik, and S. Faazil Int. J. Med. Biol. Front. 16 2010 535 568
16. A. Kamal, S. Azeeza, M.S. Malik, A.A. Shaik, M.V. Rao, and J. Pharm Pharmaceut. Sci. 11 2008 56s 80s
17. C.K. Stover, P. Warrener, D.R. VanDevanter, D.R. Sherman, T.M. Arain, M.H. Langhorne, S.W. Anderson, J.A. Towell, Y. Yuan, D.N. McMurray, B.N. Kreiswirth, C.E. Barry, and W.R. Baker Nature 405 2000 962 966
18. M. Matsumoto, H. Hashizume, T. Tomishige, M. Kawasaki, H. Tsubouchi, H. Sasaki, Y. Shimokawa, and Y. Komatsu PLoS Med. 3 2006 2131 2144
19. R. Maccari, R. Ottana, F. Monforte, and M.G. Vigorita Antimicrob. Agents Chemother. 46 2002 294 299
20. B.M. Saunder, and C. Cheers Infect. Immun. 63 1995 2282 2287
21. S.G. Franzblau, R.S. Witzig, J.C. MeLaughlin, P. Torres, G. Madico, A. Harmendez, and R.H. Degnan J. Clin. Microbiol. 36 1998 362 366
22. L.E. Bermudez, C.B. Inderlied, P. Kolonoski, M. Wu, P. Aralar, and L.S. Young Antimicrob. Agents Chemother. 45 2001 2210 2214
23. M. Kumar, I.A. Khan, V. Verma, N. Kalyan, and G.N. Qazi Diag. Microbiol. Infect. Dis. 53 2005 121 124
24. Clinical and Laboratory Standards Institute Methods for antimicrobial susceptibility testing of aerobic bacteria (M07-A8) Approved Standard ninth ed. 2008 National Committee for Clinical Laboratory Standards Wayne, PA
25. S.B. Levy, and B. Marshall Nat. Med. 10 2004 S122 S129
26. D.J. Payne, M.N. Gwynn, D.J. Holmes, and D.J. Pompliano Nat. Rev. Drug Discov. 6 2006 29 40
27. R.J. Wallace Jr., D.R. Nash, L.C. Steele, and V. Steingrube J. Clin. Microbiol. 24 1986 976 981
28. M.E. Lindy Practical Introduction to Microbiology 1962 E&F.N. Spon Ltd pp. 177)
29. K. Falzari, Z.H. Zhu, D.H. Pan, H.W. Liu, P. Hongmanee, and S.G. Franzblau Antimicrob. Agents Chemother. 49 2005 1447 1454