Abstract
A series of N6-alkyladenosine 3', 5'-cyclic phosphates (N6-alkyl cAMPs) (3) and N6-alkyl-8-benzylthio cAMPs (4) was synthesized from cAMP (1) and 8-benzylthio cAMP (2) by means of a one-pot reaction. This reaction proceeded by reductive alkylation in acetic acid with aldehydes and sodium cyanoborohydride. These cAMP derivatives were evaluated for inotropic and chronotropic effects on the isolated guinea pig papillary muscle and right atria. Several N6-alkyl cAMPs (3) were surprisingly more active than compounds 4 in these actions. Among them, N6-hexyl cAMP (3f) and M6-heptyl cAMP (3g) showed strongly positive inotropic effects (PIE) and moderately negative chronotropic effects.
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