Halogenated Boldine Derivatives with Enhanced Monoamine Receptor Selectivity
Sobarzo_Eduardo.pdf (67.10Kb)Abstract
(S)-(+)-Boldine (1) was brominated, chlorinated, and iodinated using molecular bromine in acetic acid or
N-halosuccinimides in trifluoroacetic acid. Initial halogenation occurs at C-3, followed (in the cases of
chlorine and bromine) by the less reactive C-8, to afford 3-haloboldines- and 3,8-dihaloboldines (2-5).
Using a 2:1 ratio of N-iodosuccinimide to boldine, however, only the 3-iodo derivative 6 was obtained.
Radioligand binding studies of these products showed that halogenation of boldine at C-3 favors affinity
for D1- (vs D2-) dopaminergic receptors, attaining a low nanomolar IC50 value in the case of 3-iodoboldine
(6).
Patrocinador
This work was funded in part by the
Presidential Chair in Science (B.K.C., Chile, 1996). The
principal author acknowledges a generous gift of equipment
from the Alexander von Humboldt Foundation (Germany). An
exchange program between France and Chile (ECOS/CONICYT)
made valuable face-to-face discussions possible. E.M.S.
is the recipient of a FONDECYT scholarship.
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J. Nat. Prod., Vol. 63, p. 480-484, 2000.
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