Structure function relationship study of yuehchukene. I. Anti-implantation and estrogenic activities of substituted yuehchukene derivatives

Article abstract of DOI:10.1016/0223-5234(91)90099-9

(+/-)-Yuehchukene (YCK) is a novel bis-indole alkaloid with potent anti-implantation activity in rats.The present paper reports the activity of YCK derivatives by substitution on the parent compound.Substitutions on the indole nitrogens or on 2- and 5'-positions of the indole moiety abolished activity.N-1'-methylation of the free indole only permitted a 30percent residual activity.Saturation of the C9-C10 cyclohexenyl double bond did not affect activity at all.Hydroxylation, whether on the C9-C10 double bond, or at C2 or C5, rendered the hydroxylated derivatives inactive.This suggests that the active metabolite in anti-implantation was probably not a hydroxylated derivative carrying estrogenic activity.