Betulinic acid and dihydrobetulinic acid derivatives and uses th

Details Betulinic acid and dihydrobetulinic acid derivatives and uses th Betulinic acid and dihydrobetulinic acid derivatives and uses th

1995-06-05

1997-10-21

Dees, Jose G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560194, 514120, 514253, 514258, 514418, 514510, C07C 69753, A61K 31505, A61K 3152, A61K 31215

Patent

active

056798288

ABSTRACT:
Some betulinic acid and dihydrobetulinic acid acyl derivatives according to the present invention have been found to have potent anti-HIV activity. Introducing a C.sub.2 -C.sub.20 substituted or unsubstituted acyl group at the C.sub.3 -hydroxy group of betulinic acid and dihydrobetulinic acid produces the corresponding 3-O-acyl derivatives. The compounds of the present invention have the following formulae: ##STR1## where R may be a mono- or dicarboxylacyl group, substituted or unsubstituted, of from about 2 to about 20 carbon atoms, and R' may be hydrogen or a C.sub.2 -C.sub.10 substituted and unsubstituted alkyl or aryl group.

REFERENCES:
patent: 5468888 (1995-11-01), Bouboutou et al.
Fujioka et al., Betulinic Acid and Platanic Acid as Anti-HIV Principles from Syzigium claviflorum, and the Anti-HIV Activity of Structurally Related Triterpenoids, J. Natural Products 57(2):243-247 (1994).
Fujioka et al. "Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids". J. Natural Products, vol. 57(2): 243-247, 1994.
Klinor et al. "Triterpenes. XXI. 3,4-seco derivatives of betulinic acid". Collect. Czech. Chem. Commun. vol. 37(2): 603-609, 1972.
Mayaux et al. "Triterpene derivatives that block entry of human immunodeficiency virus type 1 into cells". Proc. Natl. Acad. Sci. vol. 91(9): 3564-3568, 1994.

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