Synthesis and antiviral property of allophenylnorstatine-based HIV protease inhibitors incorporating d-cysteine derivatives as P2/P3 moieties

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 15, 2007, Pages 4213-4217

  Ami, Ei'ichi ^a   Nakahara, Koichiro ^b   Sato, Akihiko ^b   Nguyen, Jeffrey Tri ^a   Hidaka, Koushi ^a   Hamada, Yoshio ^a   Nakatani, Shingo ^a   Kimura, Tooru ^a   Hayashi, Yoshio ^a   Kiso, Yoshiaki ^a  

^a Center for Frontier Research in Medicinal Science   (Japan)

^b SHIONOGI AND CO LTD   (Japan)

Author keywords

Allophenylnorstatine; d Cysteine; Drug resistant HIV strain; HIV protease; Protease inhibitor

Indexed keywords

ALLOPHENYLNORSTATINE; CYSTEINE DERIVATIVE; DEXTRO CYSTEINE DERIVATIVE; KNI 1931; KNI 1932; KNI 1933; KNI 1946; KNI 1947; KNI 1961; KNI 1964; KNI 1965; KNI 1966; KNI 1969; KNI 1986; KNI 1990; KNI 764; KYNOSTATIN 272; NELFINAVIR; PROTEINASE; PROTEINASE INHIBITOR; RITONAVIR; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS; NONHUMAN; STRUCTURE ANALYSIS; VIRUS STRAIN;

AMIDES; CELL LINE; CYSTEINE; HIV; HIV PROTEASE INHIBITORS; HUMANS; MODELS, MOLECULAR; PHENYLBUTYRATES; THIAZOLES;

EID: 34347390406     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.05.039     Document Type: Article

References (25)

1. Wlodawer A., Miller M., Jaskilolski M., Sathyanarayana B.K., Baldwin E., Weber I.T., Selk L., Clawson L., Schneider J., and Kent S.B.H. Science 245 (1989) 616
2. Navia M.A., Fitzgerald P.M.D., McKeever B.M., Leu C.-T., Heimbach J.C., Herber W.K., Sigal I.S., Darke P.L., and Springer J.P. Nature 337 (1989) 615
3. Lappoto R., Blundell T., Hemmings A., Overington J., Wilderspin A., Wood S., Merson J.R., Whittle P.J., Danley D.E., Geoghegan K.F., Hawrylik S.J., Lee S.E., Scheld K.G., and Hobart P.M. Nature 342 (1989) 299
4. Kohl N.E., Emini E.A., Schleif W.A., Davis L.J., Heimbach J.C., Dixon R.A.F., Scolnick E.M., and Sigal I.S. Proc. Natl. Acad. Sci. U.S.A. 85 (1988) 4686
5. Chrusciel R.A., and Strohbach J.W. Curr. Top. Med. Chem. 4 (2004) 1097
6. Randolph J.T., and DeGoey D. Curr. Top. Med. Chem. 4 (2004) 1079
7. Lebon F., and Ledecq M. Curr. Med. Chem. 7 (2000) 455
8. Huff J.R., and Kahn J. Adv. Protein Chem. 56 (2001) 213
9. AIDS Info-A service of the U.S. Department of Health and Human Services (http://aidsinfo.nih.gov/).
10. Tamamura H., Koh Y., Ueda S., Sasaki Y., Yamasaki T., Aoki M., Maeda K., Watai Y., Arikuni H., Otaka A., Mitsuya H., and Fujii N. J. Med. Chem. 46 (2003) 1764
11. Grabar S., Pradier C., Corfec E.L., Lancar R., Allavena C., Bentana M., Berlureau P., Dupont C., Peray P.F., Martin I.P., and Costagliola D. AIDS 14 (2000) 141
12. Mimoto T., Imai J., Kisanuki S., Enomoto H., Hattori N., Akaji K., and Kiso Y. Chem. Pharm. Bull. 40 (1992) 2251
13. Mimoto T., Kato R., Takaku H., Nojima S., Terashima K., Misawa S., Fukazawa T., Ueno T., Sato H., Shintani M., Kiso Y., and Hayashi H. J. Med. Chem. 42 (1999) 1789
14. Balden E.T., Bhat T.N., Gulnlk S., Leu B., Topol I.A., Kiso Y., Mimoto T., Mitsuya H., and Erickson J.W. Structure 3 (1995) 581
15. Kato R., Takahashi O., Kiso Y., Moriguchi I., and Hirono S. Chem. Pharm. Bull. 42 (1994) 176
16. Wang J.X., DiPasquale A.J., Bray A.M., Maeji N.J., and Geysen H.M. Bioorg. Med. Chem. Lett. 3 (1993) 451
17. Spellmeyer D.C., Brown S., Stauber G.B., Geysen H.M., and Valerio R. Bioorg. Med. Chem. Lett. 3 (1993) 1253
18. Shepherd T.A., Jungheim L.N., and Baxter A.J. Bioorg. Med. Chem. Lett. 4 (1994) 1391
19. Munroe J.E., Shepherd T.A., Jungheim L.N., Hornback W.J., Hatch S.D., Muesing M.A., Wiskerchen M., Su K.S., Campanale K.M., Baxter A.J., and Colacino J.M. Bioorg. Med. Chem. Lett. 5 (1995) 2897
20. Jungheim L.N., Shepherd T.A., Baxter A.J., Burgess J., Hatch S.D., Lubbehusen P., Wiskerchen M., and Muesing M.A. J. Med. Chem. 39 (1996) 96
21. Horiki K. Tetrahedron Lett. 18 (1977) 1897
22. Kataoka H., and Katagi T. Chem. Pharm. Bull. 37 (1989) 3166
23. Arnold L.D., Kalantar T.H., and Vederas J.C. J. Am. Chem. Soc. 107 (1985) 7105
24. 3 were modified to form the desired inhibitor. Ideal ionization states for Asp25A and Asp25B were decided after examining different permutations. An interacting water molecule (present in both PDB 1MSM and 1HPX) was added. Inhibitor and PR residues with hydrogen bond interactions to inhibitor were made flexible. Energy minimization (force field MMFF94x) was performed after each step.
25. Mosmann T. J. Immuol. Methods 65 (1983) 55