Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: Novel antibacterial agents against Mycobacterium tuberculosis

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 21, 2010, Pages 6306-6309

  Li, Xiaokai ^a   Liu, Nina ^a   Zhang, Huaning ^a   Knudson, Susan E ^b   Slayden, Richard A ^b   Tonge, Peter J ^a  

^a STONY BROOK UNIVERSITY   (United States)

^b Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

1,4 Benzoxazine; 1,4 Dihydroxy 2 naphthoyl CoA synthase; Menaquinone; MenB; Mycobacterium tuberculosis

Indexed keywords

1,4 BENZOXAZINE; ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

ANTITUBERCULAR AGENTS; BENZOXAZINES; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; OXO-ACID-LYASES; STRUCTURE-ACTIVITY RELATIONSHIP;

MYCOBACTERIUM TUBERCULOSIS;

EID: 77957886578     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.08.076     Document Type: Article

References (20)

1. A. Kochi Tubercle 72 1991 1
2. B.R. Bloom, and C.J.L. Murray Science 257 1992 1055
3. T.P. Begley, C. Kinsland, S. Taylor, M. Tandon, R. Nicewonger, M. Wu, H.J. Chiu, N. Kelleher, N. Campobasso, and Y. Zhang F.J. Leeper, J.C. Vederas, Biosynthesis - Polyketides and Vitamins. Topics in Current Chemistry Vol. 195 1998 Springer Berlin 93
4. R. Meganathan Vitam. Horm. 61 2001 173
5. J.J. Truglio, K. Theis, Y. Feng, R. Gajda, C. Machutta, P.J. Tonge, and C. Kisker J. Biol. Chem. 278 2003 42352
6. K. Kobayashi, S.D. Ehrlich, A. Albertini, G. Amati, K.K. Andersen, M. Arnaud, K. Asai, S. Ashikaga, S. Aymerich, P. Bessieres, F. Boland, S.C. Brignell, S. Bron, K. Bunai, J. Chapuis, L.C. Christiansen, A. Danchin, M. Debarbouille, E. Dervyn, E. Deuerling, K. Devine, S.K. Devine, O. Dreesen, J. Errington, S. Fillinger, S.J. Foster, Y. Fujita, A. Galizzi, R. Gardan, C. Eschevins, T. Fukushima, K. Haga, C.R. Harwood, M. Hecker, D. Hosoya, M.F. Hullo, H. Kakeshita, D. Karamata, Y. Kasahara, F. Kawamura, K. Koga, P. Koski, R. Kuwana, D. Imamura, M. Ishimaru, S. Ishikawa, I. Ishio, D. Le Coq, A. Masson, C. Mauel, R. Meima, R.P. Mellado, A. Moir, S. Moriya, E. Nagakawa, H. Nanamiya, S. Nakai, P. Nygaard, M. Ogura, T. Ohanan, M. O'Reilly, M. O'Rourke, Z. Pragai, H.M. Pooley, G. Rapoport, J.P. Rawlins, L.A. Rivas, C. Rivolta, A. Sadaie, Y. Sadaie, M. Sarvas, T. Sato, H.H. Saxild, E. Scanlan, W. Schumann, J. Seegers, J. Sekiguchi, A. Sekowska, S.J. Seror, M. Simon, P. Stragier, R. Studer, H. Takamatsu, T. Tanaka, M. Takeuchi, H.B. Thomaides, V. Vagner, J.M. van Dijl, K. Watabe, A. Wipat, H. Yamamoto, M. Yamamoto, Y. Yamamoto, K. Yamane, K. Yata, K. Yoshida, H. Yoshikawa, U. Zuber, and N. Ogasawara Proc. Natl. Acad. Sci. U.S.A. 100 2003 4678
7. X.Q. Lu, H.N. Zhang, P.J. Tonge, and D.S. Tan Bioorg. Med. Chem. Lett. 18 2008 5963
8. Y. Tian, D.H. Suk, F. Cai, D. Crich, and A.D. Mesecar Biochemistry 47 2008 12434
9. M. Kurosu, P. Narayanasamy, K. Biswas, R. Dhiman, and D.C. Crick J. Med. Chem. 50 2007 3973
10. J.J. Truglio, K. Theis, Y.G. Feng, R. Gajda, C. Machutta, P.J. Tonge, and C. Kisker J. Biol. Chem. 278 2003 42352
11. W.E. O'Brien Anal. Biochem. 76 1976 423
12. C.W. Lindsley, Z.J. Zhao, W.H. Leister, R.G. Robinson, S.F. Barnett, D. Defeo-Jones, R.E. Jones, G.D. Hartman, J.R. Huff, H.E. Huber, and M.E. Duggan Bioorg. Med. Chem. Lett. 15 2005 761
13. L.E. Seitz, W.J. Suling, and R.C. Reynolds J. Med. Chem. 45 2002 5604
14. R. Fringuelli, N. Giacche, L. Milanese, E. Cenci, A. Macchiarulo, A. Vecchiarelli, G. Costantino, and F. Schiaffella Bioorg. Med. Chem. 17 2009 3838
15. W. He, M.R. Myers, B. Hanney, A.P. Spada, G. Bilder, H. Galzcinski, D. Amin, S. Needle, K. Page, Z. Jayyosi, and M.H. Perrone Bioorg. Med. Chem. Lett. 13 2003 3097
16. D.S. La, J. Belzile, J.V. Bready, A. Coxon, T. DeMelfi, N. Doerr, J. Estrada, J.C. Flynn, S.R. Flynn, R.F. Graceffa, S.P. Harriman, J.F. Larrow, A.M. Long, M.W. Martin, M.J. Morrison, V.F. Patel, P.M. Roveto, L. Wang, M.M. Weiss, D.A. Whittington, Y. Teffera, Z.Y. Zhao, A.J. Polverino, and J.C. Harmanget J. Med. Chem. 51 2008 1695
17. V. Gein, N. Rassudikhina, and E. Voronina Pharm. Chem. J. 40 2006 554
18. A. Babenysheva, N. Lisovskaya, I. Belevich, and N. Lisovenko Pharm. Chem. J. 40 2006 611
19. V. Gein, N. Rassudikhina, N. Shepelina, M. Vakhrin, E. Babushkina, and E. Voronina Pharm. Chem. J. 42 2008 529
20. I. Mashevskaya, I. Tolmacheva, É. Voronova, T. Odegova, G. Aleksandrova, A. Goleneva, S. Kol'tsova, and A. Maslivets Pharm. Chem. J. 36 2002 32