Design, synthesis, and biological evaluation of 4-(5-nitrofuran-2-yl)prop- 2-en-1-one derivatives as potent antitubercular agents

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 21, 2010, Pages 6175-6178

  Tawari, Nilesh R ^a   Bairwa, Ranjeet ^a   Ray, M K ^b   Rajan, M G R ^b   Degani, Mariam S ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b TATA MEMORIAL HOSPITAL   (India)

Author keywords

4 (5 Nitrofuran 2 yl)prop 2 en 1 one; Antitubercular; Lowest unoccupied molecular orbital (LUMO); Molecular electrostatic profile (MESP)

Indexed keywords

3 (5 NITROFURAN 2 YL) 1 (4 (PIPERIDIN 1 YL)PHENYL)PROP 2 EN 1 ONE); 4 (5 NITROFURAN 2 YL)PROP 2 EN 1 ONE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG DESIGN; DRUG SELECTIVITY; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS;

ANIMALS; ANTITUBERCULAR AGENTS; CELL SURVIVAL; CERCOPITHECUS AETHIOPS; DRUG DESIGN; FURANS; INDICATORS AND REAGENTS; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MYCOBACTERIUM TUBERCULOSIS; PROPIOPHENONES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS;

MYCOBACTERIUM TUBERCULOSIS;

EID: 77957881436     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.08.127     Document Type: Article

References (25)

1. J.F. Murray Respiration 65 1998 335
2. C. Dye, S. Scheele, P. Dolin, V. Pathania, and M.C. Raviglione J. Am. Med. Assoc. 282 1999 677
3. http://www.who.int/mediacentre/factsheets/fs104/en/index.html.
4. B.R. Bloom, Tuberculosis: Pathogenesis, Protection, and Control 1994 ASM Press Washington, DC
5. M. Zignol, M.S. Hosseini, A. Wright, C.L. Weezenbeek, P. Nunn, C.J. Watt, B.G. Williams, and C. Dye J. Infect. Dis. 194 2006 479
6. S.T. Cole, R. Brosch, J. Parkhill, T. Garnier, C. Churcher, D. Harris, S.V. Gordon, K. Eiglmeier, S. Gas, C.E. Barry III, F. Tekaia, K. Badcock, D. Basham, D. Brown, T. Chillingworth, R. Connor, R. Davies, K. Devlin, T. Feltwell, S. Gentles, N. Hamlin, S. Holroyd, T. Hornsby, K. Jagels, A. Krogh, J. McLean, S. Moule, L. Murphy, K. Oliver, J. Osborne, M.A. Quail, M.A. Rajandream, J. Rogers, S. Rutter, K. Seeger, J. Skelton, R. Squares, S. Squares, J.E. Sulston, K. Taylor, S. Whitehead, and B.G. Barrell Nature 393 1998 537
7. R.D. Fleischmann, D. Alland, J.A. Eisen, L. Carpenter, O. White, J. Peterson, R. DeBoy, R. Dodson, M. Gwinn, D. Haft, E. Hickey, J.F. Kolonay, W.C. Nelson, L.A. Umayam, M. Ermolaeva, S.L. Salzberg, A. Delcher, T. Utterback, J. Weidman, H. Khouri, J. Gill, A. Mikula, W. Bishai, W.R. Jacobs Jr., J.C. Venter, and C.M. Fraser J. Bacteriol. 184 2002 5479
8. C.E. Barry III, H.I. Boshoff, and C.S. Dowd Curr. Pharm. Des. 10 2004 3239
9. R.F. Anderson, S.S. Shinde, A. Maroz, M. Boyd, B.D. Palmer, and W.A. Denny Org. Biomol. Chem. 6 2008 1973
10. R. Singh, U. Manjunatha, H.I.M. Boshoff, Y.H. Ha, P. Niyomrattanakit, R. Ledwidge, C.S. Dowd, I.Y. Lee, P. Kim, L. Zhang, S. Kang, T.H. Keller, J. Jiricek, and C.E. Barry III Science 322 2008 1392
11. S. Dharmarajan, Y. Perumal, D. Prathiba, S. Palaniappan, B. Debjani, and H.M. Thimmappa Bioorg. Med. Chem. Lett. 19 2009 1152
12. Lee, R.; Tangallapally, R. P.; McNeil, M. R.; Anne, L. WO 2005/007625.
13. G. Devaux, A. Nuhrich, R. Dargelos, and M. Capdepuy Eur. J. Med. Chem. 12 1977 21
14. N.R. Tawari, and M.S. Degani J. Comput. Chem. 31 2010 739
15. C.A. Valdez, J.C. Tripp, Y. Miyamoto, J. Kalisiak, P. Hruz, Y.S. Andersen, S.E. Brown, K. Kangas, L.V. Arzu, B.J. David, F.D. Gillin, J.A. Upcroft, P. Upcroft, V.V. Fokin, D.K. Smith, K.B. Sharpless, and L. Eckmann J. Med. Chem. 13 2009 4038
16. Jaguar, version 7.5 Schrödinger, LLC, New York, NY.
17. R - 5.46.
18. J.C. Palomino, A. Martin, M. Camacho, H. Guerra, J. Swings, and F. Portaels Antimicrob. Agents Chemother. 46 2002 2720
19. R. Bairwa, M. Kakwani, N.R. Tawari, J. Lalchandani, M.K. Ray, M.G.R. Rajan, and M.S. Degani Bioorg. Med. Chem. Lett. 20 2010 1623
20. M. Matsumoto, H. Hashizume, T. Tomishige, M. Kawasaki, H. Tsubouchi, H. Sasaki, Y. Shimokawa, and M. Komatsu PLoS Med. 3 2006 2131
21. P. Kim, L. Zhang, U.H. Manjunatha, R. Singh, S. Patel, J. Jiricek, T.H. Keller, H.I. Boshoff, C.E. Barry III, and C.S. Dowd J. Med. Chem. 52 2009 1317
22. Phase, version 2.0 Schrödinger, LLC, New York, NY.
23. S. Bag, N.R. Tawari, S.F. Queener, M.S. Degani, J. Enzyme Inhib. Med. Chem. doi: 10.3109/14756360903179443.
24. R.P. Tangallapally, D. Sun, Rakesh, N. Budha, R.E.B. Lee, A.J.M. Lenaerts, B. Meibohm, and R.E. Lee Bioorg. Med. Chem. Lett. 17 2007 6638
25. G.R. Brown, A.J. Foubister, and P.D. Ratcliffe Tetrahedron Lett. 40 1999 1219