New Hypocholesterolemic Abietamide Derivatives. II. Synthesis and Hypocholesterolemic Activity of N-Phenyl-Δ⁸-dihydroabietamides

Abstract

A series of N-phenyl-Δ⁸-dihydroabietamide analogs were prepared and tested for hypocholesterolemic activity. The effects of substituents of the phenyl moiety on the activities were quantitatively analyzed by using various substituent parameters. The activities were enhanced by the electron-donating effect of ortho and para substituents and the bulkiness of ortho substituents. A combination of 2, 6-dimethylaniline with resin acids other than Δ⁸-dihydroabietic acid produced lower activities than N-(2, 6-dimethylphenyl)-Δ⁸-dihydroabietamide, abietane-type carboxamides being somewhat stronger than pimarane-type carboxamides. The conversion of the carboxamide group to other groups resulted in more or less of a decrease in activity, giving evidence that the carboxamide group is important to hypocholesterolemic activity.