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Two series of half acid esters of succinic and glutaric acids were synthesized and assayed for inhibition of rat liver β‐hydroxy‐β‐methylglutaryl coenzyme A reductase. Irreversible inhibition was studied by incorporation of a potential alkylating group (the epoxide function) into the side chain of the alcohol portion of the half acid esters. Incorporation of a terminal olefin function into the side chain of the alcohol portion of the half acid esters provided a group that could form a charge–transfer complex. Neither irreversible inhibition nor formation of a charge–transfer complex was indicated from these studies; however, the two series of half acid esters exhibited reversible inhibition.

A series of half acid esters of 1‐(4‐biphenylyl)pentanol was synthesized and assayed for inhibition of rat liver β‐hydroxy‐β‐methylglutaryl coenzyme A reductase. The number of methylenes separating the carboxyl and ester groups was varied from zero to six. A minimum of one methylene was required for reasonable activity. Further separation of the carboxyl and ester groups produced small changes in activity. Investigation of several isomeric ( cis and trans ) half acid esters indicated that activity was independent of configuration. Modification of the acid portion of the glutarate analog by incorporating a 3‐hydroxyl group increased activity sixfold.

A series of 4-substituted aminoquinoline-3-carboxylates was prepared and evaluated for antimicrobial activity. Four of the compounds (VIII, XIII, XV, and XXIII) exhibited low activity against Staphylococcus aureus.

Eleven substituted 4-biphenylylalkyl carboxylic acids and three methyl esters were synthesized and assayed for inhibition of rat liver beta-hydroxy-beta-methylglutaryl coenzyme A reductase. Five of the acids were analogs, resulting from various isosteric replacements of the carbonyl and ether oxygens of the previously described reversible inhibitor 1-(4-biphenylyl)pentyl hydrogen succinate. No significant change in activity was noted, except upon introduction of an amide linkage where a decrease in inhibition was found. Six carboxylic acids and three methyl esters, all containing the 4-biphenylyl radical but lacking the n-butyl side chain found in 1-(4-biphenylyl)pentyl hydrogen succinate, also were inhibitors of the reductase.