Regioselectivity and reactivity in microsomal hydroxylation of a series of N-acyl- and N-sulfonylamines in rats.
Regioselectivity and overall reactivity in the hydroxylation of a series of substituted N-benzoyl- and benzenesulfonyl aliphatic and alicyclic amines with rat liver microsomes were investigated. The hydroxylation occurred predominantly at the position gamma to the nitrogen atom. para-Alkyl-substituted benzoylamines were hydroxylated at both the benzylic positions as well as the gamma-position, whereas para-substituted benzenesulfonylamines were hydroxylated mainly at the benzylic position. The relative overall reactivity of primary, secondary, and tertiary carbon atoms was about 1:3:8, and the contribution of substituents adjoining to the reaction site was negligible. Benzylic hydroxylation proceeded stereoselectively, whereas gamma-hydroxylation gave optically inactive metabolites; the inter- and intramolecular isotope effects in the hydroxylation were 1.6 and 7.2, respectively.[1]References
- Regioselectivity and reactivity in microsomal hydroxylation of a series of N-acyl- and N-sulfonylamines in rats. Shono, T., Ohmizu, Y., Toda, T., Oshino, N. Drug Metab. Dispos. (1981) [Pubmed]
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