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Electronic effects of para-substitution on acetophenones in the reaction of rat liver 3alpha-hydroxysteroid dehydrogenase.

Abstract：

:Stereoselective reductive metabolism of various p-substituted acetophenone derivatives was studied using isolated rat liver 3alpha-hydroxysteroid dehydrogenase (3alpha-HSD). Kinetic experiments were performed and analyzed by measuring the products by HPLC using a chiral column. The results demonstrated that the presence of an electron-withdrawing substituent on the benzene ring plays an important role in determining the reduction rate in the syntheses of various (S)-alcohols from their corresponding carbonyl compounds. A plot of log {(V(max)/K(m))X/(V(max)/K(m))H} versus the substituent parameter (pi, sigma(para), Es) shows an increasing rate mainly for electron-withdrawing substituents, with a correlation coefficient (r(2)) of 0.97 which was obtained for triplicate data that were significant at the p<0.0001 level. With this in mind, new drugs can be designed that exploit this reduction pathway by introducing an electron-withdrawing group adjacent to the reduction site when a reduction reaction is desired, or by adding an electron-donating group when minimization of the reduction pathway is desired.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Uwai K,Konno N,Yasuta Y,Takeshita M

doi

10.1016/j.bmc.2007.10.096

subject

Has Abstract

pub_date

2008-02-01 00:00:00

pages

1084-9

issue

3

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(07)00963-7

journal_volume

16

pub_type

杂志文章

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