Configuration and leishmanicidal activity of (-)-argentilactone epoxides.
Epoxidation of argentilactone (1) with m-chloroperbenzoic acid gave a diasteromeric mixture of 2 and 3 in a ratio 1.8 : 1, with total yield 60%. The configuration of 7,8-oxirane ring for both diasteromers was determined by NMR analysis. Reaction of 1 with urea hydrogen peroxide gave the 3,4-epoxide (4) in 65% yield. The in vitro activity of 2, 3, 4 and argentilactone against Leishmania amazonensis was tested, only epoxides (2) and (3) showed leishmanicidal effect.
Cortés
Manuel J
MJ
Depto. Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, Casilla, 306, Santiago 22, Chile. mcortesm@uc.cl
Armstrong
Veronica
V
Barrero
Alejandro F
AF
Bandoni
Arnaldo E
AE
Priestap
Horacio A
HA
Fournet
Alain
A
Prina
Eric
E
D000818:Animals; D000981:Antiprotozoal Agents / Q000494:pharmacology*; D004852:Epoxy Compounds / Q000737:chemistry* / Q000494:pharmacology*; D007783:Lactones / Q000737:chemistry* / Q000494:pharmacology*; D007891:Leishmania / Q000187:drug effects*; D015394:Molecular Structure
C515763:6R,7R,8R-argentilactone-7,8-epoxide; D000981:Antiprotozoal Agents; D004852:Epoxy Compounds; D007783:Lactones; C108954:argentilactone