Synthesis and in vitro antimycobacterial activity of 8-OCH3 ciprofloxacin methylene and ethylene isatin derivatives

European Journal of Medicinal Chemistry

Volumn 46, Issue 1, 2011, Pages 341-348

  Feng, Lian Shun ^a   Liu, Ming Liang ^a   Zhang, Shu ^b   Chai, Yun ^a   Wang, Bo ^a   Zhang, Yi Bin ^a   Lv, Kai ^a   Guan, Yan ^a   Guo, Hui Yuan ^a   Xiao, Chun Ling ^a  

^a INSTITUTE OF MEDICINAL BIOTECHNOLOGY   (China)

^b BEIJING UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

8 OCH3 ciprofloxacin derivatives; Antimycobacterial activity; Synthesis

Indexed keywords

1 CYCLOPROPYL 6 FLUOR O 8 METHOXY 7 [4 (BETA METHOXYIMINOISATINYL)METHYLPIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 (2 ISATINYLETHYL)PIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 (5 FLUORINISATINYL BETA ETHOXYIMINO)METHYLPIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 (5 FLUORINISATINYL BETA HYDROXIMINO)METHYLPIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 (5 FLUORINISATINYL BETA METHOXYIMINO)METHYLPIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 (5 FLUORINISATINYL BETA SEMICARBAZO)METHYLPIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 (5 FLUOROISATINYLMETHYL)PIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 (BETA ETHOXYIMINOISATINYL)METHYLPIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 (BETA HYDROXIMINOISATINYL)METHYLPIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 (BETA SEMICARBAZOISATINYL)METHYLPIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 (BETA THIOSEMICARBAZOISATINYL)METHYLPIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 (ISATINYLMETHYL)PIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 [2 (5 FLUORINISATINYL BETA ETHOXYIMINO)ETHYL]PIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 [2 (5 FLUORINISATINYL BETA HYDROXIMINO)ETHYL]PIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 [2 (5 FLUORINISATINYL BETA METHOXYIMINO)ETHYL]PIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 [2 (5 FLUORINISATINYL BETA SEMICARBAZO)ETHYL]PIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 [2 (5 FLUORINISATINYL BETA THIOSEMICARBAZO)ETHYL]PIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 [2 (5 FLUOROISATINYL)ETHYL]PIPERAZIN 1 YL]1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 [2 (BETA ETHOXYIMINOISATINYL)ETHYL]PIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 [2 (BETA METHOXYIMINOISATINYL)ETHYL]PIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 [2 (BETA SEMICARBAZOISATINYL)ETHYL]PIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 [2 (BETA THIOSEMICARBAZOISATINYL)ETHYL]PIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; ANTIMYCOBACTERIAL AGENT; CIPROFLOXACIN; CYCLOPROPYL 6 FLUORO 8 METHOXY 7 [4 [2 (BETA HYDROXIMINOISATINYL)ETHYL]PIPERAZIN 1 YL] 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; ISATIN DERIVATIVE; ISONIAZID; RIFAMPICIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; LIPOPHILICITY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM SMEGMATIS; NONHUMAN;

ANIMALS; ANTI-BACTERIAL AGENTS; CERCOPITHECUS AETHIOPS; CIPROFLOXACIN; ISATIN; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM; OXIMES; SEMICARBAZONES; VERO CELLS;

EID: 78650516933     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.11.023     Document Type: Article

References (23)

1. X.M. Wei, A.D. Rodríguez, Y.H. Wang, and S.G. Franzblau Bioorg. Med. Chem. Lett. 18 2008 5448 5450
2. WHO Global Tuberculosis Control a Short Update to the 2009 Report 2009 World Health Organization Geneva
3. WHO 2009 Update Tuberculosis Facts 2009 World Health Organization Geneva
4. R.P. Tripathi, N. Saxena, V.K. Tiwari, S.S. Verma, V. Chaturvedi, Y.K. Manju, A.K. Srivastva, A. Gaikwadc, and S. Sinha Bioorg. Med. Chem. 14 2006 8186 8196
5. D. Sriram, P. Yogeeswari, and S.P. Reddy Bioorg. Med. Chem. Lett. 16 2006 2113 2116
6. K. Duncan, and C.E. Barry Curr. Opin. Microbiol. 7 2004 460 465
7. D.C. Hooper, and J.S. Wolfson N. Engl. J. Med. 32 1991 384 394
8. A.M. Emmerson, and A.M. Jones J. Antimicrob. Chemother. 51 2003 13 20
9. P.S. Charifson, A.L. Grillot, T.H. Grossman, J.D. Parsons, M. Badia, S. Bellon, D.D. Deininger, J.E. Drumm, C.H. Gross, A. LeTiran, Y.S. Liao, N. Mani, D.P. Nicolau, E. Perola, S. Ronkin, D. Shannon, L.L. Swenson, Q. Tang, P.R. Tessier, S.K. Tian, M. Trudeau, T.S. Wang, Y.Y. Wei, H. Zhang, and D. Stamos J. Med. Chem. 51 2008 5243 5263
10. A. Aubry, X.S. Pan, L.M. Fisher, V. Jarlier, and C. Emmanuelle Antimicrob. Agents Chemother. 48 2004 1281 1288
11. G. Anquetiin, J. Greiner, N. Mahmoud, M.H. Santillana, R. Gozalbes, K. Farhati, F. Derouin, E. Cambau, and P. Vierling Eur. J. Med. Chem. 41 2006 1478 1493
12. D. Sriram, P. Yogeeswari, J.S. Basha, D.R. Radha, and V.J. Nagaraja Bioorg. Med. Chem. 13 2005 5774 5778
13. Guidelines for the Management of Drug-Resistant Tuberculosis WHO/TB/96-210 (Rev.1) 1997 World Health Organization Geneva
14. S.H. Zhao, R. Pine, J. Domagala, and K. Drlica Antimicrob. Agents Chemother. 43 1999 661 666
15. A.S. Ginsburg, J.H. Grosset, and W.R. Bishai Lancet Infect. Dis. 3 2003 432 442
16. J.P. Sanchez, R.D. Gogliotti, J.M. Domagala, S.J. Gracheck, M.D. Huband, J.A. Sesnie, M.A. Cohen, and M.A. Shapiro J. Med. Chem. 38 1995 4478 4487
17. H. Koga, A. Itoh, S. Murayama, S. Suzue, and T. Irikura J. Med. Chem. 23 1980 1358 1363
18. Z. Dang, Y.S. Yang, R.Y. Ji, and S.H. Zhang Bioorg. Med. Chem. Lett. 17 2007 4523 4526
19. L.L. Shen, L.A. Mitscher, P.N. Sharma, T.J. Odonnell, D.W.T. Chu, C.S. Cooper, T. Rosen, and A.G. Pernet Biochemistry 28 1989 3886 3894
20. D. Sriram, A. Aubry, P. Yogeeswaria, and L.M. Fisher Bioorg. Med. Chem. Lett. 16 2006 2982 2985
21. L.S. Feng, M.L. Liu, B. Wang, Y. Chai, X.Q. Hao, S. Meng, and H.Y. Guo Eur. J. Med. Chem. 45 2010 3407 3412
22. E. Piscopo, M.V. Diurno, R. Gogliadi, M. Cucciniello, and G. Veneruso Boll. Soc. Ital. Biol. Sper. 63 1987 827 832
23. Y. Chai, Z.L. Wan, B. Wang, H.Y. Guo, and M.L. Liu Eur. J. Med. Chem. 44 2009 4063 4069