Synthesis and antitubercular activity of monocyclic nitroimidazoles: Insights from econazole

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 5, 2011, Pages 1515-1518

  Lee, Sang Ho ^a   Kim, Suhyun ^a,c   Yun, Min Han ^a   Lee, Yong Sup ^c   Cho, Sang Nae ^b   Oh, Taegwon ^b   Kim, Pilho ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b Yonsei University College of Medicine   (South Korea)

^c Kyung Hee University   (South Korea)

Author keywords

Anaerobic activity; Econazole; Nitroimidazole; Tuberculosis

Indexed keywords

4 NITRO ECONAZOLE; ECONAZOLE; MONOCYCLIC NITROIMIDAZOLE; NITROIMIDAZOLE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTITUBERCULAR ACTIVITY; ARTICLE; CANDIDA ALBICANS; CONCENTRATION RESPONSE; CYTOTOXICITY TEST; DRUG ACTIVITY; DRUG DESIGN; DRUG MECHANISM; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN;

ANTIFUNGAL AGENTS; ANTITUBERCULAR AGENTS; CYCLIZATION; DRUG DESIGN; ECONAZOLE; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; NITROIMIDAZOLES;

MYCOBACTERIUM TUBERCULOSIS;

EID: 79951723342     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.12.128     Document Type: Article

References (19)

1. http://www.who.int/mediacentre/factsheets/fs104/en/index.html.
2. http://clinicaltrials.gov/ct2/show/NCT00567840.
3. http://clinicaltrials.gov/ct2/show/NCT00685360.
4. C.E. Barry 3rd, H.I. Boshoff, and C.S. Dowd Curr. Pharm. Des. 10 2004 3239
5. H.S. Sutherland, A. Blaser, I. Kmentova, S.G. Franzblau, B. Wan, Y. Wang, Z. Ma, B.D. Palmer, W.A. Denny, and A.M. Thompson J. Med. Chem. 53 2010 855
6. B.D. Palmer, A.M. Thompson, H.S. Sutherland, A. Blaser, I. Kmentova, S.G. Franzblau, B. Wan, Y. Wang, Z. Ma, and W.A. Denny J. Med. Chem. 53 2010 282
7. P. Kim, L. Zhang, U.H. Manjunatha, R. Singh, S. Patel, J. Jiricek, T.H. Keller, H.I. Boshoff, C.E. Barry 3rd, and C.S. Dowd J. Med. Chem. 52 2009 1317
8. P. Kim, S. Kang, H.I. Boshoff, J. Jiricek, M. Collins, R. Singh, U.H. Manjunatha, P. Niyomrattanakit, L. Zhang, M. Goodwin, T. Dick, T.H. Keller, C.S. Dowd, and C.E. Barry 3rd J. Med. Chem. 52 2009 1329
9. K.J. McLean, K.R. Marshall, A. Richmond, I.S. Hunter, K. Fowler, T. Kieser, S.S. Gurcha, G.S. Besra, and A.W. Munro Microbiology 148 2002 2937
10. C.J. Jackson, D.C. Lamb, D.E. Kelly, and S.L. Kelly FEMS Microbiol. Lett. 192 2000 159
11. Z. Ahmad, S. Sharma, and G.K. Khuller FEMS Microbiol. Lett. 261 2006 181
12. Z. Ahmad, S. Sharma, G.K. Khuller, P. Singh, J. Faujdar, and V.M. Katoch Int. J. Antimicrob. Agents 28 2006 543
13. Z. Ahmad, S. Sharma, and G.K. Khuller Nanomed. Nanotechnol. Biol. Med. 3 2007 239
14. Z. Ahmad, R. Pandey, S. Sharma, and G.K. Khuller Int. J. Antimicrob. Agents 31 2008 142
15. Baker, W. R.; Shaopei, C.; Keeler, E. L. U.S. Patent 6,087,358, 2000.
16. L.A. Collins, and S.G. Franzblau Antimicrob. Agents Chemother. 41 1997 1004
17. L.A. Collins, M.N. Torrero, and S.G. Franzblau Antimicrob. Agents Chemother. 42 1998 344
18. Wayne, L. G.; Hayes, L. G. Infect. Immun. 1996, 64, 2062. The detailed experimental procedure for the MIC under anaerobic conditions is as follows: Mtb H37Rv-GFP was grown in tight-sealed test tube with 0.5-head space ratio for 14 days. Initial compound solution was prepared in DMSO, and two fold serial dilutions were made in DMSO in a microplate. The serially-diluted compound solution was dispensed in a microplate, and Mtb H37Rv-GFP in non-replicating phase was dispensed in the plate in an anaerobic chamber. The plates containing compounds dilutions and Mtb H37Rv-GFP were incubated at 37 °C for 7 days in the anaerobic chamber. After exposure Mtb H37Rv-GFP was diluted 10 fold in fresh media, and incubated for 2 days. The fluorescence was measured in a Fluostar Optima microplate fluorometer (BMG Labtech., Germany) in the bottom-reading mode with excitation at 485 nm and emission at 520 nm. The MIC against non-replicating Mtb was defined as the lowest concentration of compounds that inhibited fluorescence by 80%, compared to the fluorescence of bacteria only wells.
19. R.N. Tiballi, X. He, L.T. Zarins, S.G. Revankar, and C.A. Kauffman J. Clin. Microbiol. 33 1995 915