Design, synthesis and antifungal activity of isosteric analogues of benzoheterocyclic N-myristoyltransferase inhibitors

European Journal of Medicinal Chemistry

Volumn 45, Issue 9, 2010, Pages 3531-3540

  Sheng, Chunquan ^a   Xu, Hui ^a   Wang, Wenya ^a   Cao, Yongbing ^a   Dong, Guoqiang ^a   Wang, Shengzheng ^a   Che, Xiaoying ^a   Ji, Haitao ^b   Miao, Zhenyuan ^a   Yao, Jianzhong ^a   Zhang, Wannian ^a  

^a SECOND MILITARY MEDICAL UNIVERSITY   (China)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

Antifungal activity; Benzoxazole; Indole; N Myristoyltransferase inhibitors

Indexed keywords

2 (CHLOROMETHYL)BENZOXAZOL 4 OL; 2 AMINOBENZENE 1,3 DIOL; 3 [2 (PHENOXYMETHYL)BENZOXAZOL 4 YLOXY] N (PYRIDIN 3 YLMETHYL)PROPAN 1 AMINE; 3 [2 [(2 FLUOROPHENOXY)METHYL]BENZOXAZOL 4 YLOXY] N (PYRIDIN 3 YLMETHYL) PROPAN 1 AMINE; 3 [2 [(2,4 DIFLUOROPHENOXY)METHYL]BENZOXAZOL 4 YLOXY} N (PYRIDIN 3 YL METHYL)PROPAN 1 AMINE; 3 [2 [(3 NITROPHENOXY)METHYL]BENZOXAZOL 4 YLOXY] N (PYRIDIN 3 YLMETHYL) PROPAN 1 AMINE; 3 [2 [(4 FLUOROPHENOXY)METHYL]BENZOXAZOL 4 YLOXY] N (PYRIDIN 3 YLMETHYL) PROPAN 1 AMINE; 3-[2-[(2,6 DIFLUOROPHENOXY)METHYL]BENZOXAZOL 4 YLOXY] N (PYRIDIN 3 YL METHYL)PROPAN 1 AMINE; BENZOXAZOLE DERIVATIVE; FLUCONAZOLE; N (PYRIDIN 3 YLMETHYL) 3 {2 [(2,3,4 TRIFLUOROPHENOXY) METHYL]BENZOXAZOL 4 YLOXY}PROPAN 1 AMINE; N (PYRIDIN 3 YLMETHYL) 3 {2 [(2,4,6 TRIFLUOROPHENOXY) METHYL]BENZOXAZOL 4 YLOXY]PROPAN 1 AMINE; PROTEIN N MYRISTOYLTRANSFERASE INHIBITOR; TERT BUTYL 2 (CHLOROMETHYL)BENZOXAZOL 4 YL CARBONATE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; HUMAN; HYDROGEN BOND; HYDROGENATION; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; NONHUMAN;

ACYLTRANSFERASES; ANTIFUNGAL AGENTS; BENZOXAZOLES; CANDIDA ALBICANS; CATALYTIC DOMAIN; DRUG DESIGN; ENZYME INHIBITORS; INDOLES; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77955557244     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.03.007     Document Type: Article

References (28)

1. S.K. Fridkin, and W.R. Jarvis Clin. Microbiol. Rev. 9 1996 499 511
2. J.P. Latge Clin. Microbiol. Rev. 12 1999 310 350
3. J.N. Steenbergen, and A. Casadevall J. Clin. Microbiol. 38 2000 1974 1976
4. M.B. Edmond, S.E. Wallace, D.K. McClish, M.A. Pfaller, R.N. Jones, and R.P. Wenzel Clin. Infect. Dis 29 1999 239 244
5. A. Minari, R. Husni, R.K. Avery, D.L. Longworth, M. DeCamp, M. Bertin, R. Schilz, N. Smedira, M.T. Haug, A. Mehta, and S.M. Gordon Transpl. Infect. Dis 4 2002 195 200
6. H.A. Gallis, R.H. Drew, and W.W. Pickard Rev. Infect. Dis. 12 1990 308 329
7. D.J. Sheehan, C.A. Hitchcock, and C.M. Sibley Clin. Microbiol. Rev. 12 1999 40 79
8. D.W. Denning J. Antimicrob. Chemother. 49 2002 889 891
9. I.A. Casalinuovo, P. Di Francesco, and E. Garaci Eur. Rev. Med. Pharmacol. Sci. 8 2004 69 77
10. J.A. Boutin Cell. Signal. 9 1997 15 35
11. T.A. Farazi, G. Waksman, and J.I. Gordon J. Biol. Chem. 276 2001 39501 39504
12. N.H. Georgopapadakou Expert Opin. Investig. Drugs 11 2002 1117 1125
13. B. Devadas, S.K. Freeman, C.A. McWherter, N.S. Kishore, J.K. Lodge, E. Jackson-Machelski, J.I. Gordon, and J.A. Sikorski J. Med. Chem. 41 1998 996 1000
14. B. Devadas, S.K. Freeman, M.E. Zupec, H.F. Lu, S.R. Nagarajan, N.S. Kishore, J.K. Lodge, D.W. Kuneman, C.A. McWherter, D.V. Vinjamoori, D.P. Getman, J.I. Gordon, and J.A. Sikorski J. Med. Chem. 40 1997 2609 2625
15. B. Devadas, M.E. Zupec, S.K. Freeman, D.L. Brown, S. Nagarajan, J.A. Sikorski, C.A. McWherter, D.P. Getman, and J.I. Gordon J. Med. Chem. 38 1995 1837 1840
16. S.R. Nagarajan, B. Devadas, M.E. Zupec, S.K. Freeman, D.L. Brown, H.F. Lu, P.P. Mehta, N.S. Kishore, C.A. McWherter, D.P. Getman, J.I. Gordon, and J.A. Sikorski J. Med. Chem. 40 1997 1422 1438
17. L.A. Paige, G.Q. Zheng, S.A. DeFrees, J.M. Cassady, and R.L. Geahlen Biochemistry 29 1990 10566 10573
18. K. Parang, E.E. Knaus, L.I. Wiebe, S. Sardari, M. Daneshtalab, and F. Csizmadia Arch. Pharm. (Weinheim) 329 1996 475 482
19. H. Ebiike, M. Masubuchi, P. Liu, K. Kawasaki, K. Morikami, S. Sogabe, M. Hayase, T. Fujii, K. Sakata, H. Shindoh, Y. Shiratori, Y. Aoki, T. Ohtsuka, and N. Shimma Bioorg. Med. Chem. Lett. 12 2002 607 610
20. K. Kawasaki, M. Masubuchi, K. Morikami, S. Sogabe, T. Aoyama, H. Ebiike, S. Niizuma, M. Hayase, T. Fujii, K. Sakata, H. Shindoh, Y. Shiratori, Y. Aoki, T. Ohtsuka, and N. Shimma Bioorg. Med. Chem. Lett. 13 2003 87 91
21. M. Masubuchi, H. Ebiike, K. Kawasaki, S. Sogabe, K. Morikami, Y. Shiratori, S. Tsujii, T. Fujii, K. Sakata, M. Hayase, H. Shindoh, Y. Aoki, T. Ohtsuka, and N. Shimma Bioorg. Med. Chem. 11 2003 4463 4478
22. M. Masubuchi, K. Kawasaki, H. Ebiike, Y. Ikeda, S. Tsujii, S. Sogabe, T. Fujii, K. Sakata, Y. Shiratori, Y. Aoki, T. Ohtsuka, and N. Shimma Bioorg. Med. Chem. Lett. 11 2001 1833 1837
23. K. Yamazaki, Y. Kaneko, K. Suwa, S. Ebara, K. Nakazawa, and K. Yasuno Bioorg. Med. Chem. 13 2005 2509 2522
24. S. Ebara, H. Naito, K. Nakazawa, F. Ishii, and M. Nakamura Biol. Pharm. Bull. 28 2005 591 595
25. S. Sogabe, M. Masubuchi, K. Sakata, T.A. Fukami, K. Morikami, Y. Shiratori, H. Ebiike, K. Kawasaki, Y. Aoki, N. Shimma, A. D'Arcy, F.K. Winkler, D.W. Banner, and T. Ohtsuka Chem. Biol. 9 2002 1119 1128
26. C. Sheng, J. Zhu, W. Zhang, M. Zhang, H. Ji, Y. Song, H. Xu, J. Yao, Z. Miao, Y. Zhou, and J. Lu Eur. J. Med. Chem. 42 2007 477 486
27. C. Sheng, W. Zhang, H. Ji, M. Zhang, Y. Song, H. Xu, J. Zhu, Z. Miao, Q. Jiang, J. Yao, Y. Zhou, and J. Lu J. Med. Chem. 49 2006 2512 2525
28. Insight II, 2000, Accelrys Inc., 10188 Telesis Court, Suite 100, San Diego, CA 92121. Phone: (858) 799-5000. fax: (858) 799-5100. Website: http://www.accelrys.com/.