Inhibitors of hepatic mixed function oxidase. 3. Inhibition of hepatic microsomal aniline hydroxylase and aminopyrine demethylase by 2,6- and 2,4-dihydroxyphenyl alkyl ketones and related compounds

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Abstract
A series of 2,6- and 2,4-dihydroxyphenyl alkyl ketones was investigated as inhibitors of [rat] hepatic microsomal aniline hydroxylase and aminopyrine demethylase activities. Structural alterations in both series did little to enhance inhibitory activity of the parent compounds 2,6-dihydroxyacetophenone and 2,4-dihydroxyacetophenone. In the 2,6 series, activity against both microsomal systems varied only over a relatively narrow range, 6-allyloxy-2-hydroxyacetophenone being the most potent inhibitor. In the 2,4 series, activity against aniline hydroxylase was poor or absent in most cases. The most potent inhibitor was 5-ethyl-2,4-dihydroxyacetophenone. In contrast, high activity against aminopyrine demethylase was frequently displayed in this series, 3,5-dibromo-2,4-dihydroxypropiophenone showing greatest inhibitory potency. Effects of some compounds on hexobarbital sleeping times and zoxazolamine paralysis times in mice were also examined.