An efficient synthesis of aryloxyphenyl cyclopropyl methanones: A new class of anti-mycobacterial agents

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 20, 2005, Pages 4526-4530

  Dwivedi, Namrata ^a   Tewari, Neetu ^a   Tiwari, V K ^a   Chaturvedi, Vinita ^a   Manju, Y K ^a   Srivastava, A ^a   Giakwad, A ^a   Sinha, S ^a   Tripathi, R P ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Phenyl cyclopropyl methanones; Tetrabutylammonium bromide; Tuberculosis; Wolf Kishner reduction

Indexed keywords

ALCOHOL; ANTIMYCOBACTERIAL AGENT; BUTYROPHENONE DERIVATIVE; CARBENE; CYCLOPROPANE DERIVATIVE; ETHAMBUTOL; ISONIAZID; RIFAMPICIN;

ANIMAL CELL; ANIMAL MODEL; ARTICLE; DRUG SYNTHESIS; EVALUATION; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MOUSE; MULTIDRUG RESISTANCE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROVOCATION; TUBERCULOSIS;

ANIMALS; ANTITUBERCULAR AGENTS; METHANE; MICE; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS;

EID: 24344447290     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.07.007     Document Type: Article

References (38)

1. E. Stokstad Science 287 2000 2391
2. WHO Global tuberculosis programme-Tuberculosis Fact Sheet, 2002. World Health Organisation. Global Tuberculosis Control, WHO Report 2001.
3. World Health Organisation, Geneva, Switzerland, WHO/CDS/TB/2001, 287. http://www.who.int/mediacentre/factsheets/who104/en/index.html.
4. N. Mooran Nat. Med. 2 1996 377
5. C. Dye, S. Scheele, P. Dolin, V. Pathania, and M.C. Raviglione J. Am. Med. Assoc. 282 1999 677
6. S.W. Dooley, W.R. Jarvis, W.J. Martone, and D.E. Snyder Jr. Ann. Int. Med. 117 1992 257
7. M.C. Raviglione, D.E. Snider Jr., and A. Kochi JAMA 273 1995 220
8. P. Farmer, J. Bayona, M. Beccera, J. Henry, C. Furin, H.;. Hiarr, J.Y. Kim, C. Mimic, E. Nardell, and S. Shin Int. J. Tuberc. Lung. Dis. 2 1998 869
9. Hudson, A.; Imamura, T.; Gutteridge, W.; Kanyok, T.; Nunn, P. The current anti-TB drug research and development pipeline WHO TDR/PRD/03.1W Geneva, 2003.
10. R.P. Tripathi, N. Tewari, N. Dwivedi, and V.K. Tiwari Med. Res. Rev. 25 2005 93
11. I. Chopra, and P. Brennan Tubercle Lung Dis. 78 2 1988 89
12. J.S. Blanchard Ann. Rev. Biochem. 65 1996 215
13. D. Mitchison, and P. Nunn Am. Rev. Resp. Dis. 133 1986 423
14. S.T. Cole, R. Brosch, J. Parkhill, T. Garnier, C. Churcher, D. Harris, S.V. Gordon, K. Eiglmeier, S. Gas, C.E. Barry, F. Tekaia, K. Badcock, D. Basham, D. Brown, T. Chillingworth, R. Conner, R. Davies, K. Devlin, T. Feltwell, S. Gentless, N. Hamlin, S. Holrod, T. Hornsby, K. Jagels, A. Krogh, J. Mclean, S. Moule, L. Murphy, K. Oliver, S.J. Osborne, M.A. Quail, M.A. Rajandream, J. Rogers, S. Rutter, K. Seeger, J. Skeleton, R. Squares, S. Squares, J.E. Sulston, K. Taylor, S. Whitehead, and B.G. Barrel Nature 393 1998 537 and references cited therein
15. J.H. Richard, W.W. Stephen, and O.R. Charles Progr. Lipid Res. 40 2001 467
16. L. Rajabi, C. Courreges, J. Montoya, R.J. Aguilera, and T.P. Primm Lett. Appl. Microbiol. 40 2005 212
17. Y.M. Lin, Y. Zhou, M.T. Flavin, L.M. Zhou, W. Nie, and F.C. Chen Bioorg. Med. Chem. 10 2002 2795
18. M.A. Morgan, K.A. Doerr, H.O. Hampel, N.L. Goodman, and G.D. Roberts J. Clin. Microbiol. 21 1985 634
19. N. Rastogi, K.S. Goh, and H.L. David Res. Microbiol. 140 1989 419
20. Novel phenyl cyclopropyl methanones useful as antitubercular agents. Grover, R. K.; Mishra, R. C.; Verma, S. S.;Tripathi, R. P.; Roy, R.; Srivastava, R.; Srivastava, A. Chaturvedi, V.; Krishana, M.Y.; Srivasatava, B. S.; Lal, J.; Gupta, R.C 036DEL2004 Filing Date 31/3/04 New Delhi.
21. C.E. Barry III, R.E. Lee, and K. Mdluli Progr. Lipid Res. 37 1998 143
22. C. Hansch, P.G. Sammes, J.B. Taylor, and C.J. Dryton Comprehensive Medicinal Chemistry Vol. 6 1990 Pergamon Oxford, UK
23. A.M.P. Koshikenen, and H. Hassila Acta Chem. Scan. 50 1996 323
24. M. Shi, Y.H. Yang, and B. Xu Tetrahedron 61 2005 1893 and references cited therein
25. H.M.L. Davies Tetrahedron 49 1993 5203
26. J. Mann Tetrahedron 42 1986 4611
27. E. Peirs B.M. Trost Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford 899 971
28. T. Hudlicky, R. Fan, J. Reed, and K.G. Gadasetty Org. React. 41 1992 1
29. R.E. Taylor, F.C. Engelhardt, and M.J. Schmitt Tetrahedron 59 2003 5623
30. R.K. Grover, R.C. Mishra, B. Kundu, R.P. Tripathi, and R. Roy Tetrahedron Lett. 43 2004 7331
31. 2F (270): C, 75.55; H, 5.55; Found: C, 75.31; H, 5.64.
32. 2F (272): C, 75.00; H, 6.25; Found: C, 74.89; H, 6.50.
33. 17OF (256): C, 79.68; H, 6.64; Found: C, 79.80; H, 6.89.
34. 3F (327): C, 73.39; H, 6.11; Found: C, 73.50; H, 6.31.
35. U. Gerhard, J.P. Mackay, R.A. Maplestone, and D.H. Williams J. Am. Chem. Soc. 115 1993 232
36. G.H. Caughey, W.W. Raymond, E. Bucci, R.J. Lamberdy, and R.R. Tidwell J. Pharmacol. Exp. Ther. 264 1993 676
37. M. Garcia, X. del. Rio, S. Silvestre, M. Rubiralta, E. Lozoya, V. Segarra, D. Fernandez, M. Miralpeix, M. Aparici, and A. Diez Org. Biomol. Chem. 2 2004 1633
38. V.K. Tiwari, N. Tewari, D. Katiyar, R.P. Tripathi, K. Arora, S. Gupta, A.K. Srivastava, M.A. Khan, and P.K. Murthy Bioorg. Med. Chem. 11 2003 1789