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Title:
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Halogenated Boldine Derivatives with Enhanced Monoamine Receptor Selectivity |
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Author:
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Sobarzo-Sánchez, Eduardo M.; Arbaoui, Jeannette; Protais, Philippe; Cassels, Bruce K.
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Abstract:
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(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). |
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URI:
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http://www.captura.uchile.cl/handle/2250/16651
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Date:
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2000-03-15 |
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dc.identifier.citation:
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J. Nat. Prod., Vol. 63, p. 480-484, 2000. |