Generation and exploration of new classes of antitubercular agents: The optimization of oxazolines, oxazoles, thiazolines, thiazoles to imidazo[1,2-a]pyridines and isomeric 5,6-fused scaffolds

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 7, 2012, Pages 2214-2220

  Moraski, Garrett C ^a   Markley, Lowell D ^a   Chang, Mayland ^a   Cho, Sanghyun ^b   Franzblau, Scott G ^b   Hwang, Chang Hwa ^b   Boshoff, Helena ^c   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^c NATIONAL INSTITUTE OF ALLERGY AND INFECTIOUS DISEASES   (United States)

Author keywords

5,6 Fused heteroaromatics; Imidazo 1,2 a pyridine; MDR TB; Mycobacterium tuberculosis; XDR TB

Indexed keywords

IMIDAZO[1,2 A]PYRIDINE DERIVATIVE; IMIDAZO[1,2 A]PYRIMIDINE DERIVATIVE; IMIDAZO[1,2 C]PYRIMIDINE DERIVATIVE; ISONIAZID; OXAZOLE DERIVATIVE; OXAZOLINE DERIVATIVE; PYRIMIDINE DERIVATIVE; RIFAMPICIN; THIAZOLE DERIVATIVE; THIAZOLINE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CONTROLLED STUDY; DRUG POTENCY; DRUG RESISTANCE; DRUG SENSITIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN;

ANTITUBERCULAR AGENTS; ISOMERISM; ISOXAZOLES; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; OXAZOLES; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

MYCOBACTERIUM TUBERCULOSIS;

EID: 84863416201     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.02.025     Document Type: Article

References (25)

1. Global tuberculosis control WHO report 2011. WHO/HTM/TB/2011.16.
2. Snider, D. E. Jr.; Raviglione, M.; Kochi, A. Global Burden of Tuberculosis, Tuberculosis: Pathogenesis, Protection, and Control, ASM Press: Washington, D.C., 1994.
3. J.C. Sacchettini, E.J. Rubin, and J.S. Freundlich Nat. Rev. Microbiol. 6 2008 41
4. Tuberculosis: A global emergency. 1993. World Health Forum 14:438.
5. G.C. Moraski, M. Chang, A. Villegas-Estrada, S. Franzblau, U. Möllmann, and M.J. Miller Eur. J. Med. Chem. 45 2010 1703
6. G.C. Moraski, S.G. Franzblau, and M.J. Miller Heterocycles 80 2009 977
7. Miller, M. J.; Hu, J. US Patent 6,403,623 B1, 2002.
8. G.C. Moraski, L.D. Markley, P.A. Hipskind, H. Boshoff, S. Cho, S.G. Franzblau, and M.J. Miller Med. Chem. Lett. 2 2011 466
9. Miller, M. J.; Moraski, G. C.; Markley, L. D.; Davis, G. E. WO 2011/057145 A2, 2011.
10. A.J. Phillips, Y. Uto, P. Wipf, M.J. Reno, and D.R. Williams Org. Lett. 2 2000 1165
11. D.R. Williams, P.D. Lowder, Y.G. Gu, and D.A. Brooks Tetrahedron Lett. 38 1997 331
12. Bergeron, R. J. US Patent 6,559,315 B1, 2003.
13. L. Collins, and S.G. Franzblau Antimicrob. Agents Chemother. 41 1997 1004
14. J.J. De Voss, K. Rutter, B.G. Schroeder, H. Su, Y. Zhu, and C.E. Barry Proc. Nat. Acad. Sci. U.S.A. 97 2000 1252
15. K. Pethe, P.C. Sequeira, S. Agarwalla, K. Rhee, K. Kuhen, W.Y. Phong, V. Patel, D. Beer, J.R. Walker, J. Duraiswamy, J. Jiricek, T.H. Keller, A. Chatterjee, M.P. Tan, M. Ujjini, S.P.S. Roa, L. Camacho, P. Bifani, P.A. Mak, I. Ma, and S.W. Barnes Nat. Commun. 57 2010 1
16. S.H. Cho, S. Warit, B. Wan, C.H. Hwang, G.F. Pauli, and S.G. Franzblau Antimicrob. Agents Chemother. 51 2007 1380
17. A.A. Minnick, J.A. McKee, E.K. Dolence, and M.J. Miller Antimicrob Agents Chemother. 36 1992 840
18. M.J. Miller, G. Zhao, S. Vakulenko, S. Franzblau, and U. Möllmann Org. Biomol. Chem. 4 2006 4178
19. A. Lilienkampf, M. Pieroni, B. Wan, Y. Wang, S.G. Franzblau, and A.P. Kozikowski J. Med. Chem. 53 2010 678
20. Simulated gastric fluid and simulated intestinal fluid. In The United States Pharmacopeia 23, The National Formulary 18. The United States Pharmacopeial Convention, Inc., Rockville, MD, 1995, 2053.
21. L.R. Odell, M.T. Nilsson, J. Gising, O. Lagerlund, D. Muthas, A. Nordqvist, A. Karlen, and M. Larhed J. Med. Chem. Lett. 19 2009 4790
22. T.H. Al-Tel, and R.A. Al-Qawasmeh Eur. J. Med. Chem. 45 2010 5848
23. G. Harth, and M.A. Horwitz J. Exp. Med. 189 1999 1425
24. C.K. Stover, P. Warrener, D.R. VanDevanter, D.R. Sherman, T.M. Arain, M.H. Langhorne, S.W. Anderson, J.A. Towell, Y. Yuan, D.N. McMurray, B.N. Kreiswirth, C.E. Barry, and W.R. Baker Nature 405 2000 962
25. U.H. Manjunatha, H. Boshoff, C.S. Dowd, L. Zhang, T.J. Albert, J.E. Norton, L. Daniels, T. Dick, S.S. Pang, and C.E. Barry Proc. Natl. Acad. Sci. U.S.A. 103 2006 431