Potential antiatherosclerotic agents. 3. Substituted benzoic and nonbenzoic acid analogs of cetaben

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Abstract
The synthesis of a series of analogs in which the carboxylic acid group of cetaben is replaced by carboxylate ester, carboxamide or a variety of other substituent groups is described. Also reported are the syntheses of analogs in which the phenyl ring of cetaben is either modified by the presence of additional substituents or replaced entirely by another moiety. Structure-activity relationships of these compounds both as hypolipidemic agents and as inhibitors of the enzyme fatty acyl-CoA:cholesterol acyltransferase (ACAT) [in rats] are discussed. Analog syntheses designed to produce compounds that would be better absorbed orally than cetaben failed to yield any congeners of enhanced biological activity. Analog syntheses directed toward non-carboxylic acids of similar acidity to cetaben produced a very active class of sulfonamides.