Antimycobacterial activities of novel 2-(sub)-3-fluoro/nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]quinoline-6 -carboxylic acid

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 6, 2008, Pages 3408-3418

  Dinakaran, Murugesan ^a   Senthilkumar, Palaniappan ^a   Yogeeswari, Perumal ^a   China, Arnab ^b   Nagaraja, Valakunja ^a   Sriram, Dharmarajan ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

^b INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Antimycobacterial activity; Antitubercular activity; Benzothiazoloquinolone; Tuberculosis

Indexed keywords

2 (1,4 DIOXA 8 AZASPIRO[4.5]DEC 8 YL) 3 NITRO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 (2 CARBOXY 5,6 DIHYDROIMIDAZO[1,2 A]PYRAZIN 7(8H) 3 NITRO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 (2,6 DIMETHYLMORPHOLINO) 3 FLUORO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 (3,4 DIHYDRO 6,7 DIMETHOXYISOQUINOLIN 2(1H) YL) 3 NITRO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 (4 METHYL 3 PHENYLPIPERAZIN 1 YL) 3 NITRO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 (6 TERT BUTOXYCARBONYLAMINO 3 AZABICYCLO[3.1.0]HEX 3 YL) 3 NITRO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 [1 (TERT BUTYLCARBAMOYL) 3,4 DIHYDROISOQUINOLIN 2(1H)YL] 3 FLUORO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 [3 (2,6 DIFLUOROPHENYL)5 METHYLISOXAZOL 4 OYL](PIPERAZIN 1 YL) 3 FLUORO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 [3 (DIETHYLCARBAMOYL)PIPERIDIN 1 YL)]3 FLUORO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 [3 (DIETHYLCARBAMOYL)PIPERIDIN 1 YL] 3 FLUORO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 [4 (2 FUROYL)PIPERAZIN 1 YL] 3 NITRO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 [4 (4 CHLOROPHENYL) 4 HYDROXYPIPERIDIN 1 YL] 3 FLIORO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 [4 (6 CHLORO 1,2 DIHYDRO 2 OXOBENZO[D]IMIDAZOL 3 YL)PIPERIDIN 1 YL] 3 NITRO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 [4 (PIPERIDIN 1 YL)PIPERIDIN 1 YL] 3 NITRO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 [4 [(4 CHLOROPHENYL)(PHENYL)METHYL]PIPERAZIN 1 YL] 3 FLUORO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 [4 [(BENZO[D][1,3]DIOXO 6 YL)METHYL]PIPERAZIN 1 YL] 3 FLUORO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 [8 (4 METHOXYBENZYL) 3,4,5,6,7,8 HEXAHYDROISOQUINOLIN 2(1H) YL] 3 FLUORO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; 2 THIOMORPHOLINO 3 NITRO 5,12 DIHYDRO 5 OXOBENZOTHIAZOLO[3,2 A]QUINOLINE 6 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; DNA TOPOISOMERASE (ATP HYDROLYSING); GATIFLOXACIN; ISONIAZID; LOMEFLOXACIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG EFFICACY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; FEMALE; IN VITRO STUDY; IN VIVO STUDY; LUNG PARENCHYMA; MOUSE; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PHOTOTOXICITY; SINGLE DRUG DOSE; SPLEEN; TOXICITY TESTING; TUBERCULOSIS;

ANIMALS; ANTITUBERCULAR AGENTS; DRUG RESISTANCE, MULTIPLE, BACTERIAL; LUNG; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; QUINOLINES; SPLEEN; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA; BACTERIA (MICROORGANISMS); MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS;

EID: 41049108613     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.11.016     Document Type: Article

References (18)

1. World Health Organization, Tuberculosis fact sheet 2007.
2. Zignol M., Hosseini M.S., Wright A., Weezenbeek C.L., Nunn P., Watt C.J., Williams C.G., and Dye C. J. Infect. Dis. 194 (2006) 479
3. Sriram D., Yogeeswari P., Thirumurugan R., and Pavana R.K. J. Med. Chem. 49 (2006) 3448
4. Sriram D., Yogeeswari P., Dinakaran M., and Thirumurugan R. J. Antimicrob. Chemother. 59 (2007) 1194
5. Kubendiran G., Paramasivan C.N., Sulochana S., and Mitchison D.A. J. Chemother. 18 (2006) 617
6. Renau T.E., Sanchez J.P., Shapiro M.A., Dever J.A., Gracheck S.J., and Domagala J.M. J. Med. Chem. 38 (1995) 2974
7. Kondo H., Taguchi H., Inoue Y., Sakamoto F., and Tsukamoto G. J. Med. Chem. 33 (1990) 2012
8. Tsuzuki Y., Tomita K., Shibamori K., Sato Y., Kashimoto S., and Chiba K. J. Med. Chem. 47 (2004) 2097
9. National Committee for Clinical Laboratory Standards. Antimycobacterial susceptibility testing for Mycobacterium tuberculosis. Proposed standard M24-T. National Committee for Clinical Laboratory Standards, Villanova, Pa., 1995.
10. Gundersen L.L., Nissen-Meyer J., and Spilsberg B. J. Med. Chem. 45 (2002) 1383
11. Sriram D., Yogeeswari P., Basha J.S., Radha D.R., and Nagaraja V. Bioorg. Med. Chem. 13 (2005) 5774
12. Levine C.H., Hiasa A., and Marians K.J. Biochim. Biophys. Acta 1400 (1998) 29
13. Manjunatha U.H., Madhusudan K., Sandhya S.Visweswariah., and Nagaraja V. Curr. Sci. 79 (2000) 968
14. Ferguson J., Walker E.M., and Johnson B.E. British J. Dermat. 120 (1989) 291
15. Domagala J.M. J. Antimicrob. Chemother. 33 (1994) 685-706
16. Takayama S., Hirohashi M., Kato M., and Shimada H. J. Toxicol. Environ. Health 45 (1995) 1
17. Mayne T.N., Johnson N.J., Kluwe W.M., Lencoski D.L., and Polzer R.J. J. Antimicrob. Chemother. 39 (1997) 67
18. Manjunatha U.H., Dalal M., Chatterji M., Radha D.R., Visweswariah S.S., and Nagaraja V. Nucleic Acids Res. 30 (2002) 2144