Structure-based design of diaminopyranosides as a novel inhibitor core unit of HIV proteases

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 8, 1999, Pages 1179-1184

  Kurihara, Shinwa ^a   Tsumuraya, Takeshi ^a   Fujii, Ikuo ^a  

^a BIOMOL ENG RESEARCH INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC ANTIBODY; DIAMINOPYRANOSIDE; PROTEINASE; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

AMINO ACIDS, DIAMINO; DRUG DESIGN; HIV PROTEASE INHIBITORS; MODELS, CHEMICAL;

HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0033583474     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00154-7     Document Type: Article

References (31)

1. Debouck, C.; Metcalf, B. W. DrugDev. Res. 1990, 27, 1.
2. (a) Martin, J. A. Antiviral Res. 1992, 17, 265.
3. (b) Wlodawer, A.; Erickson, J. W. Annu. Rev. Biochem. 1993, 62, 543.
4. (c) Wlodawer, A.; Vondrasek, J. Annu. Rev. Biophys. Biomol. Struct. 1998, 27, 249.
5. (d) Rich, D. H. Inhibitors of Aspartic Proteinases. In Proteinase Inhibitors; Barrett, A. J., Salvesen, G., Eds.; Elsevier Science: New York, 1986; pp 179-218.
6. (a) Jacobsen, H.; Yasargil, K.; Winslow, D. L.; Craig, J. C.; Krohn, A.; Duncan, I. B.; Mous, J. Virology 1995, 206, 527.
7. (b) Markowitz, M. M.; Mo, H.; Kempf, D. J.; Norbeck, D. W.; Bhat, T. N.; Erickson, J. W.; Ho, D. J. Virol. 1995, 69, 701.
8. (c) Condra, J. H.; Schlelf, W. A.; Blahy, O. M.; Gabryelski, L. J.; Graham, D. J.; Quintero, J. C.; Rhodes, A.; Robbins, H. L.; Roth, E.; Shivaprakash, M.; Titus, D.; Yang, T.; Teppler, H.; Squires, K. E.; Deutsch, P. J.; Emini, E. A. Nature 1995, 374, 569.
9. (d) Ridky, T.; Leis, J. J. Biol. Chem. 1995, 270, 29621.
10. (a) Mimoto, T.; Imai, J.; Kisanuki, S.; Enomoto, H.; Hattori, N.; Akaji, K.; Kiso, Y. Chem. Pharm. Bull. 1992, 40, 2251.
11. (b) Baldwin, E. T.; Bhat, T. N.; Gulnik, S.; Liu, B.; Topol, I. A.; Kiso, Y.; Mimoto, T.; Mitsuya, H.; Erickson, J. W. Structure 1995, 3, 581.
12. (a) Backbro, K.; Lowgren, S.; Osterlund, K.; Atepo, J.; Unge, T. J. Med. Chem. 1997, 40, 898.
13. (b) Jadhav, P. K.; Ala, P.; Woerner, F. J.; Chang, C.-H.; Garber, S. S.; Anton, E. D.; Bacheler, L. T. ibid. 1997, 40, 181.
14. (c) Lam, P. Y. S.; Ru, Y.; Jadhav, P. K.; Aldrich, P. E.; DeLucca, G. V.; Eyermann, C. J.; Chang, C-H.; Emmett, G.; Holler, E. R.; Daneker, W. F.; Li, L.; Confalone, P. N.; McHugh, R. J.; Han, Q.; Li, R.; Markwalder, J. A.; Seitz, S. P.; Sharpe, T. R.; Bacheler, L. T.; Rayner, M. M.; Klabe, R. M.; Shum, L.; Winslow, D. L.; Kornhauser, D. M.; Jackson, D. A.; Erickson-Viitanen, S.; Hodge, C. N. ibid. 1996, 39, 3514.
15. (d) Sham, H. L.; Zhao, C.; Stewart, K. D.; Betebenner, D. A.; Lin, S.; Park, C. H.; Kong, X-P.; Rosenbrook, W. Jr.; Herrin, T.; Madigan, D.; Vasavanonda, S.; Lyons, N.; Molla, A.; Saldivar, A.; Marsh, K. C.; McDonald, E.; Wideburg, N. E.; Denissen, J. F.; Robins, T.; Kempf, D. J.; Plattner, J. J.; Norbeck, D. W. ibid. 1996, 59, 392.
16. (e) Hosur, M. V.; Bhat, T. N.; Kempf, D. J.; Baldwin, E. T.; Liu, B.; Gulnik, S.; Wideburg, N. E.; Norbeck, D. W.; Appelt, K.; Erickson, J. W. J. Am. Chem. Soc. 1994, 116, 847.
17. (f) Thanki, N.; Rao, J. K. M.; Foundling, S. L; Howe, W. J.; Moon, J. B.; Hui, J. O.; Tomasselli, A. G.; Heinrikson, R. L.; Thaisrivongs, S.; Wlodawer, A. Protein Science 1992, 1, 1061.
18. Fersht, A. The proteases. In Enzyme Structure and Mechanism (Second Edition); W. H. Freeman and Company: New York, 1985; pp 422-426.
19. (a) Fersht, A. ibid. pp 293-310.
20. (b) Intermolecular & Surface Forces (Second Edition), Israelachvili, J.; Academic Press Ltd.: London, 1991; pp 27-35.
21. The Protein Data Bank (Brookhaven National Laboratories) was accessed for the 3D structural information of the following accession codes: 1ajv, 1ajx, 1pro, 1qbs, 1dmp, 1hvr, 1qbr, 1qbu, 1qbt (cyclic inhibitors); 1hpx, 1hvi, 1hvl, 1hvk, 1hiv (acyclic inhibitors).
22. Plattner, J. J.; Norbeck, D. W. Obstacles to drug development from peptide leads. In Drug Discovery Technologies; Clark, R., Moos, W. H., Eds.; Ellis Horwood Ltd.:Chichester, 1990; pp 92-126.
23. (a) Lemieux, R. U.; Takeda, T.; Chung, B. Y. ACS Symp. Ser. 1976, 39, 90.
24. (b) Ogawa, T.; Nakabayashi, S. Carbohydr. Res. 1981, 97, 81.
25. (c) Campos-Valdes, M. T.; Marino-Albemas, J. R.; Verez-Bencomo, V. J. Carbohydr. Chem. 1987, 6, 509.
26. 4Na 447.1281, found 447.1270
27. 2 359.1971, found 359.1984
28. Matayoshi, E. D.; Wang, G. T.; Krafft, G. A.; Erickson, J. Science 1990, 247, 954.
29. 50 values described in this paper.
30. 4 385.1876, found 385.1878
31. 3 478.2342, found 478.2348