Impact of the central hydroxyl groups on the activity of symmetrical HIV-1 protease inhibitors derived from L-mannaric acid

Tetrahedron

Volumn 56, Issue 20, 2000, Pages 3219-3225

  Wachtmeister, Johanna ^a   Mühlman, Anna ^a   Classon, Björn ^a   Kvarnström, Ingemar ^b   Hallberg, Anders ^c   Samuelsson, Bertil ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b LINKÖPING UNIVERSITY   (Sweden)

^c UPPSALA UNIVERSITY   (Sweden)

Author keywords

Deoxygenation; HIV 1 protease; Hydrolysis; Oxidation; Peptidomimetics

Indexed keywords

ACID; HYDROXYL GROUP; MANNARIC ACID; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROLYSIS; NONHUMAN; OXIDATION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 17644434740     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00220-9     Document Type: Article

References (29)

1. Barré-Sinoussi F., Chermann J.C., Rey F., Nugeyre M.T., Chamaret S., Gruest J., Dauguet C., Axler-Blin C., Vezinet-Brun F., Rouzioux C., Rozenbaum W., Montagnier L. Science. 220:1983;68-871.
2. Gallo R.C., Sarin P.S., Gelmann E.P., Robert-Guroff M., Richardson E., Kalyanaraman V.S., Mann D., Sidhu G.D., Stahl R.E., Zolla-Pazner S., Leibowitch J., Popovic M. Science. 220:1983;865-867.
3. Clavel F., Guétard D., Brun-Vézinet F., Chamaret S., Rey M.-A., Santos-Ferreira M.O., Laurent A.G., Dauguet C., Katlama C., Rouzioux C., Klatzmann D., Champlimaud J.L., Montagnier L. Science. 233:1986;343-346.
4. McQuade T.J., Tomasselli A.G., Liu L., Karacostas V., Moss B., Sawyer T.K., Heinrikson R.L., Tarpley W.G. Science. 247:1990;454-456.
5. Seelmeier S., Schmidt H., Turk V., Von Der Helm K. Proc. Natl. Acad. Sci. 85:1988;6612-6616.
6. Kempf D.J., Sham H.L. Curr. Pharm. Design. 2:1996;225-246.
7. De Clercq E. J. Med. Chem. 38:1995;2492-2517.
8. Redshaw S. Exp. Opin. Invest. Drugs. 3:1994;273-286.
9. Wlodawer A., Erickson J.W. Ann. Rev. Biochem. 62:1993;543-585.
10. Meek T.D. J. Enzyme Inhib. 6:1992;65-98.
11. Norbeck D.W., Kempf D.J. J. Annu. Rep. Med. Chem. 26:1991;141-150.
12. Huff J.R. J. Med. Chem. 34:1991;2305-2313.
13. Kempf D.J. Methods Enzymol. 241:1994;334-354.
14. Alterman M., Björsne M., Mühlman A., Classon B., Kvarnström I., Danielsson H., Markgren P.-O., Nillroth U., Unge T., Hallberg A., Samuelsson B. J. Med. Chem. 41:1998;3782-3792.
15. Kempf D.J. Perspectives In Drug Discovery And Design. 2:1994;427-436.
16. Navia M.A., Chaturvedi P.R. Drug Discovery Today. 1:1996;179-189.
17. Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. Adv. Drug Del. Rev. 1997;3-25.
18. Herd J.K., Mayberry W.R. Carbohydr. Res. 1982, 99, 33-39. (and references cited therein).
19. Masamune S., Ma P., Okumoto H., Ellingboe J.W., Ito Y. J. Org. Chem. 49:1984;2837-2838.
20. Keglevic D., Ljevakovic D. Carbohydr. Res. 64:1978;319-322.
21. Nelson L.J., Nelson N. Tetrahedron Lett. 36:1995;7833-7836.
22. Anelli P.L., Biffi C., Montanari F., Quici S. J. Org. Chem. 52:1987;2559-2562.
23. Anelli P.L., Banfi S., Montanari F., Quici S. J. Org. Chem. 54:1989;2970-2972.
24. Ogura H., Kobayashi T., Shimizu K., Kawabe K., Takeda K. Tetrahedron Lett. 1979;4745-4746.
25. Fernandez J.M.G., Mellet C.O., Marin A.M., Fuentes J. Carbohydr. Res. 274:1995;263-268.
26. Zuccarello G., Bouzide A., Kvarnström I., Niklasson G., Svensson S.C.T., Brisander M., Danielsson H., Nillroth U., Karlén A., Hallberg A., Classon B., Samuelsson B. J. Org. Chem. 63:1998;4898-4906.
27. Markgren, P.-O.; Lindgren, M.; Nillroth, U.; Danielson, U. H. In Aspartic Proteinases, Plenum Press: New York, 1998, pp 99-103.
28. Nillroth U., Vrang L., Markgren P.-O., Hultén J., Hallberg A., Danielson H.U. Antimicrob. Agents Chemotherm. 41:1997;2383-2388.
29. Weislow O.S., Kiser R., Fine D.L., Bader J., Shoemaker R.H., Boyd M.R. J. Natl. Cancer Inst. 81:1989;577-586.