Identification of a novel class of quinoline-oxadiazole hybrids as anti-tuberculosis agents

Bioorganic and Medicinal Chemistry Letters

Volumn 26, Issue 2, 2016, Pages 645-649

  Jain, Puneet P ^a   Degani, Mariam S ^a   Raju, Archana ^a   Anantram, Aarti ^a   Seervi, Madhav ^a   Sathaye, Sadhana ^a   Ray, Muktikanta ^b   Rajan, M G R ^b  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b TATA MEMORIAL HOSPITAL   (India)

Author keywords

Bedaquiline; Isosterism; Mycobacterium tuberculosis; Oxadiazole; Quinoline

Indexed keywords

2 CHLORO 3 FORMYLQUINOLINE; 2 METHOXY 3 FORMYLQUINOLINE; 3 (2 METHOXYQUINOLIN 3 YL)ACRYLONITRILE; BEDAQUILINE; CYTOTOXIC AGENT; DIAZEPAM; DOXORUBICIN; ISONIAZID; OXADIAZOLE DERIVATIVE; QUINOLINE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; QUINOLINE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BINDING AFFINITY; COMPARATIVE STUDY; CONTROLLED STUDY; CYTOTOXICITY; DRUG IDENTIFICATION; DRUG SCREENING; DRUG SYNTHESIS; HEPG2 CELL LINE; IN VITRO STUDY; KNOEVENAGEL CONDENSATION; LIVER MICROSOME; METABOLIC STABILITY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR HYBRIDIZATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; ANIMAL; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; HEP-G2 CELL LINE; HUMAN; METABOLISM; MICROBIAL SENSITIVITY TEST; TUBERCULOSIS;

ANIMALS; ANTITUBERCULAR AGENTS; CELL SURVIVAL; HEP G2 CELLS; HUMANS; MICROBIAL SENSITIVITY TESTS; MICROSOMES, LIVER; MYCOBACTERIUM TUBERCULOSIS; OXADIAZOLES; QUINOLINES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; TUBERCULOSIS;

EID: 84952989199     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2015.11.057     Document Type: Article

References (30)

1. WHO Global Tuberculosis Report 2014 (WHO/HTM/TB/2014.08) 2014 World Health Organization Geneva, Switzerland
2. WHO Multidrug and Extensively Drug-Resistant TB (M/XDR-TB); Global Report on Surveillance and Response 2010 World Health Organization Geneva, Switzerland
3. Z.F. Udwadia, R.A. Amale, K.K. Ajbani, and C. Rodrigues Clin. Infect. Dis. 54 2012 579
4. A. Koul, E. Arnoult, N. Lounis, J. Guillemont, and K. Andries Nature 469 2011 483
5. R. Mahajan Int. J. Appl. Basic Med. Res. 3 2013 1
6. K. Andries, P. Verhasselt, J. Guillemont, H.W.H. Göhlmann, J.-M. Neefs, H. Winkler, J. Van Gestel, P. Timmerman, M. Zhu, E. Lee, P. Williams, D. de Chaffoy, E. Huitric, S. Hoffner, E. Cambau, C. Truffot-Pernot, N. Lounis, and V. Jarlier Science 307 2005
7. R.S. Upadhayaya, S.V. Lahore, A.Y. Sayyed, S.S. Dixit, P.D. Shinde, and J. Chattopadhyaya Org. Biomol. Chem. 8 2010 2180
8. J. Mao, H. Yuan, Y. Wang, B. Wan, M. Pieroni, Q. Huang, R.B. van Breemen, A.P. Kozikowski, and S.G. Franzblau J. Med. Chem. 52 2009 6966
9. K.D. Thomas, A.V. Adhikari, I.H. Chowdhury, T. Sandeep, R. Mahmood, B. Bhattacharya, and E. Sumesh Eur. J. Med. Chem. 46 2011 4834
10. P.P. Jain, M.S. Degani, A. Raju, M. Ray, and M.G.R. Rajan Bioorg. Med. Chem. Lett. 23 2013 6097
11. Z. Todres Chalcogenadiazoles: Chemistry and Applications 2011 CRC Press Boca Raton 32
12. G.A. Patani, and E.J. LaVoie Chem. Rev. 96 1996 3147
13. T.J. Ritchie, S.J.F. Macdonald, S. Peace, S.D. Pickett, and C.N. Luscombe MedChemComm 3 2012 1062
14. M.E. Welsch, S.a. Snyder, and B.R. Stockwell Curr. Opin. Chem. Biol. 14 2010 347
15. Schrodinger Release 2012: QikProp, Version 3.5 2012 Schrodinger, LLC New York, NY
16. S. Boyer, C.H. Arnby, L. Carlsson, J. Smith, V. Stein, and R.C. Glen J. Chem. Inf. Model. 47 2007 583
17. http://www-metaprint2d.ch.cam.ac.uk/metaprint2d.
18. O. Meth-Cohn, B. Narine, and B. Tarnowski J. Chem. Soc., Perkin Trans. 1 1981 1520
19. J.T. Kuethe, A. Wong, C. Qu, J. Smitrovich, I.W. Davies, and D.L. Hughes J. Org. Chem. 70 2005 2555
20. J.A. Montgomery, S. Niwas, J.D. Rose, J.a. Secrist, Y.S. Babu, C.E. Bugg, M.D. Erion, W.C. Guida, and S.E. Ealick J. Med. Chem. 36 1993 55
21. G.E. Stokker, W.F. Hoffman, A.W. Alberts, E.J. Cragoe, A.A. Deana, J.L. Gilfillan, J.W. Huff, F.C. Novello, J.D. Prugh, and R.L. Smith J. Med. Chem. 28 1985 347
22. B. Kaboudin, and K. Navaee Heterocycles 60 2003 2287
23. A.R. Katritzky, Y. Zhang, and S.K. Singh Synthesis (Stuttg) 6 2003 2795
24. A. Katritzky, A. Shestopalov, and K. Suzuki ARKIVOC 2005 2005 36
25. J.-C. Palomino, a. Martin, M. Camacho, H. Guerra, J. Swings, and F. Portaels Antimicrob. Agents Chemother. 46 2002 2720
26. a. Martin, M. Camacho, F. Portaels, and J.C. Palomino Antimicrob. Agents Chemother. 47 2003 3616
27. V. Vichai, and K. Kirtikara Nat. Protoc. 1 2006 1112
28. K. Iyer, P. Walawalkar, and P. Serai Indian J. Pharm. Sci. 68 2006 262
29. C.M. Masimirembwa, U. Bredberg, and T.B. Andersson Clin. Pharmacokinet. 42 2003 515
30. R.J. Riley, and K. Grime Drug Discovery Today Technol. 1 2004 365