ω-And (ω-1)-hydroxylation of 4-chloropropionanilide (cas 2759-54-8) by rabbits and rabbit liver microsomes

Add time:07/15/2019    Source:sciencedirect.com

4-Chlorolactanilide, 4-chlorohydracrylanilide, 4-chloroglyceranilide, and 4-chloroglycolanilide were isolated from urine of rabbits injected with 4-chloropropionanilide (cas 2759-54-8). The product of (ω-1)-hydroxylation amounted to nearly 30 per cent of the dose and the ω-OH derivative to about 4 per cent. An average 91 per cent of the 4-chlorolactanilide was the l-(−)-isomer. After injection of dl-4-chlorolactanilide only a small shift was found in the ratio between l- and d-isomer of the 4-chlorolactanilide isolated from urine. Rabbit liver microsomes hydroxylated 4-chloropropion-anilide more rapidly in the (ω-1)-position than in the ω-position. Ninety-three per cent of the 4-chlorolactanilide isolated was the l-(−)-isomer. 4'-chloromandelanilide isolated from urine after injection of 4'-chlorophenylacetanilide was 94% l-(+)-isomer and methylphenylcarbinol isolated after injection of ethylbenzene was 75% d-(+)-isomer. As all optically active metabolites show the same relative configuration at the asymmetric center, only the configuration at the (ω-1)-C-atom determines the hydrogen which is replaced by a hydroxyl group, the rest of the molecule affecting only binding to the enzyme and rate of hydroxylation.

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