Anti-AIDS agents - XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives

Bioorganic and Medicinal Chemistry

Volumn 5, Issue 12, 1997, Pages 2133-2143

  Hashimoto, Fumio ^a,f   Kashiwada, Yoshiki ^b,f   Cosentino, L Mark ^c   Chen, Chin Ho ^d   Garrett, Patricia E ^e   Lee, Kuo Hsiung ^f  

^a KUMAMOTO UNIVERSITY   (Japan)

^b NIIGATA UNIVERSITY OF PHARMACY AND APPLIED LIFE SCIENCES   (Japan)

^c Biotech Research Laboratories   (United States)

^d DUKE UNIVERSITY MEDICAL CENTER   (United States)

^e DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

^f UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

Anti HIV activity; Betulinic acid derivatives; Dihydrobetulinic acid derivatives

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; BETULIC ACID; RNA DIRECTED DNA POLYMERASE; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; MONONUCLEAR CELL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; VIRUS REPLICATION;

ANTI-HIV AGENTS; CELL LINE; HIV-1; HIV-1 REVERSE TRANSCRIPTASE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; T-LYMPHOCYTES; TRITERPENES;

EID: 0031467377     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(97)00158-2     Document Type: Article

References (22)

1. For part 26, see Chen, D. F.; Zhang, S. X.; Xie, L.; Xie, J. X.; Chen, K.; Kashiwada, Y.; Zhou, B. N.; Wang, P.; Cosentino, L. M.; Lee, K. H. Bioorg. Med. Chem., in press.
2. Huang, P.; Farquhar, D.; Plunkett, W. J. Biol. Chem. 1992, 267, 2817.
3. Sergheraert, C.; Pierlot, C.; Tartar, A.; Henin, Y.; Lemaitre, M. J. Med. Chem. 1993, 36, 826.
4. Biesert, L.; Zimmermann, F.; Schroder, B.; Matthes, E.; Suhartono, H.; Dietrich, U.; Rubs amen-Waigmann, H. Behring Inst. Mitt. 1991, 68, 74.
5. Gu, Z.; Fletcher, R. S.; Arts, E. J.; Wainberg, M. A.; Parniak, M. A. J. Biol. Chem. 1994, 269, 28118.
6. Najera, I.; Richman, D. D.; Olivares, I.; Rojas, J. M.; Peinado, M. A.; Perucho, M.; Najera, R.; Lopez-Galindez, C. AIDS Res. Hum. Retroviruses 1994, 10, 1479.
7. St Clair, M. H.; Martin, J. L.; Tudor-Williams, G.; Bach, M. C.; Vavro, C. L.; King, D. M.; Kellam, P.; Kemp, S. D.; Larder, B. A. Science 1991, 253, 1557.
8. Cagnon, L.; Cucchiarini, M.; Lefebvre, J. C.; Dogho, A. J. Acquir. Immune Defic. Syndr. Hum. Retrovirol. 1995, 9, 349.
9. Ghosh, A. K.; Thompson, W. J.; McKee, S. P.; Duong, T. T.; Lyle, T. A.; Chen, J. C.; Darke, P. L.; Zugay, J. A.; Emini, E. A.; Schleif, W. A.; Huff, J. R.; Anderson, P. J. Med. Chem. 1993, 36, 292.
10. Lingham, R. B.; Arison, B. H.; Colwell, L. F.; Hsu, A.; Dezeny, O.; Thompson, W. J.; Garrity, O. M.; Gagliardi, M. M.; Hartner, F. W.; Darke, P. L.; Balani, S. K.; Pitzenberger, S. M.; Murphy, J. S.; Ramjit, H. G.; Inamine, E. S.; Treiber, L. Biochem. Biophys. Res. Commun. 1991, 181, 1456.
11. Kempf, D. J.; Codacovi, L.; Wang, X. C.; Kohibrenner, W. E.; Wideburg, N. E.; Saldivar, A.; Vasavanonda, S.; Marsh, K. C.; Bryant, P.; Sham, H. L.; Green, B. E.; Betebenner, D. A.; Erickson, J.; Norbeck, W. J. Med. Chem. 1993, 36, 320.
12. Konopka, K.; Pretzer, E.; Duzgunes, N. Biochem. Biophys. Res. Commun. 1995, 208, 75.
13. Mayaux, J. F.; Bousseau, A.; Pauwels, R.; Huet, T.; Henin, Y.; Dereu, N.; Evers, M.; Soler, F.; Poujade, C.; DeClercq, E.; LePecq, J. B. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3564.
14. Mazumder, A.; Cooney, D.; Agbaria, R.; Gupta, M.; Pommier, Y. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 5771.
15. Mazumder, A.; Raghavan, K.; Weinstein, J.; Kohn, K. W.; Pommier, Y. Biochem. Pharmacol. 1995, 49, 1165.
16. Fujioka, T.; Kashiwada, Y.; Kilkuskie, R. E.; Cosentino, L. M.; Ballas, L. M.; Jiang, J. B.; Janzen, W. P.; Chen, I. S.; Lee, K. H. J. Nat Prod. 1994, 57, 243.
17. Huang, L.; Kashiwada, Y.; Cosentino, L. M.; Fan, S.; Chen, C-H.; McPhail, A. T.; Fujioka, T.; Mihashi, K.; Lee, K. H. J. Med. Chem. 1994, 37, 3947.
18. Poli, G.; Ornstein, J. M.; Kinter, A.; Folks, T. M.; Fauci, A. S. Science 1989, 244, 575.
19. Mayaux, J.; Bousseau, A.; Pauwels, R.; Huet, T.; Henin, Y.; Dereu, N.; Evers, M.; Solder, F.; Poujade, C.; DeClercq, E.; LePecq, J. B. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3564.
20. Matthews, T. J.; Weinhold, K. J.; Lyerly, H. K.; Langlois, A. J.; Wigzell, H.; Bolognesi, D. P. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 5424.
21. Clouse, K. A.; Powell, D.; Washington, I.; Poli, G.; Strebel, K.; Farrar, W.; Barstad, P.; Kovacs, J.; Fauci, A.; and Folks, T. J. Immunol. 1989, 142, 431.
22. Folks, T.; Judtement, J.; Kinter, A.; Dinarello, C.; Fauci, A. Science 1987, 238, 800.