Identification of potent type I MetAPs inhibitors by simple bioisosteric replacement. Part 2: SAR studies of 5-heteroalkyl substituted TCAT derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 18, 2005, Pages 4130-4135

  Cui, Yong Mei ^a   Huang, Qing Qing ^a   Xu, Jie ^a   Chen, Ling Ling ^a   Li, Jing Ya ^a   Ye, Qi Zhuang ^a,b   Li, Jia ^a   Nan, Fa Jun ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b UNIVERSITY OF KANSAS   (United States)

Author keywords

Bioisosteric replacement; Type I MetAPs inhibitors

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; METAL ION; METHIONYL AMINOPEPTIDASE INHIBITOR; PEPTIDE HYDROLASE INHIBITOR; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; DRUG IDENTIFICATION; ESCHERICHIA COLI; MOLECULAR SIZE; NONHUMAN; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION;

ALKYLATION; AMINOPEPTIDASES; INHIBITORY CONCENTRATION 50; ISOMERISM; MOLECULAR STRUCTURE; PROTEASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 23644441909     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.06.005     Document Type: Article

References (22)

1. R.A. Bradshaw, W.W. Brickey, and K.W. Walker Trends Biochem. Sci. 23 1998 263
2. S.M. Arfin, R.L. Kendall, L. Hall, L.H. Weaver, A.E. Stewart, B.W. Matthews, and R.A. Bradshaw Proc. Natl. Acad. Sci. U.S.A. 92 1995 7714
3. W.T. Lowther, and B.W. Matthews Chem. Rev. 102 2002 4581
4. J.T. Prchal, D.P. Cashman, and Y.W. Kan Proc. Natl. Acad. Sci. U.S.A. 83 1986 24
5. J.P. Boissel, T.J. Kasper, S.C. Shah, J.I. Malone, and H.F. Bunn Proc. Natl. Acad. Sci. U.S.A. 82 1985 8448
6. J.Y. Tso, M.A. Hermodson, and H. Zalkin J. Biol. Chem. 257 1982 3532
7. S.Y. Chang, E.C. McGary, and S. Chang J. Bacteriol. 171 1989 4071
8. C.G. Miller, A.M. Kukral, J.L. Miller, and N.R. Movva J. Bacteriol. 171 1989 5215
9. X. Li, and Y.H. Chang Proc. Natl. Acad. Sci. U.S.A. 92 1995 12357
10. E.C. Griffith, Z. Su, S. Niwayama, C.A. Ramsay, Y.H. Chang, and O.J. Liu Proc. Natl. Acad. Sci. U.S.A. 95 1998 15183
11. N. Sin, L. Meng, M.Q. Wang, J.J. Wen, W.G. Bornmann, and C.M. Crews Proc. Natl. Acad. Sci. U.S.A. 94 1997 6099
12. M.D. Vaughan, P.B. Sampson, and J.F. Honek Curr. Med. Chem. 9 2002 385
13. Q.L. Luo, J.Y. Li, Z.Y. Liu, L.L. Chen, J. Li, Z. Qian, Q. Shen, Y. Li, G.H. Livingston, Q.Z. Ye, and F.J. Nan J. Med. Chem. 46 2003 2631
14. Q.L. Luo, J.Y. Li, Z.Y. Liu, L.L. Chen, J. Li, Q.Z. Ye, and F.J. Nan Bioorg. Med. Chem. Lett. 15 2005 635
15. Q.L. Luo, J.Y. Li, L.L. Chen, J. Li, Q.Z. Ye, and F.J. Nan Bioorg. Med. Chem. Lett. 15 2005 639
16. A. Barton, S.P. Breukelman, P.T. Kaye, G. Denis Meakins, and D.J. Morgan J. Chem. Soc. Perkin. Trans. 1 1982 159
17. Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, and K.B. Sharpless J. Am. Chem. Soc. 109 1987 5765
18. Y. Gao, and K.B. Sharpless J. Org. Chem. 53 1988 4081
19. K.W. Walker, and R.A. Bradshaw Protein Sci. 7 1998 2684
20. V.M. D'souza, and R.C. Holz Biochemistry 38 1999 11079
21. V.M. D'souza, S.I. Swierczek, N.J. Cosper, L. Meng, S. Ruebush, A.J. Copik, R.A. Scott, and R.C. Holz Biochemistry 41 2002 13096
22. Q.Z. Ye, S.X. Xie, M. Huang, W.J. Huang, J.P. Lu, and Z.Q. Ma J. Am. Chem. Soc. 126 2004 13940