THEORETICAL STRUCTURE ACTIVITY STUDY OF MUTAGENIC ALLYL CHLORIDES

被引：7

作者：

BOERTH, DW ^{[1
]}

EDER, E ^{[1
]}

RASUL, G ^{[1
]}

MORAIS, J ^{[1
]}

机构：

[1] UNIV WURZBURG,INST TOXICOL,W-8700 WURZBURG,GERMANY

来源：

CHEMICAL RESEARCH IN TOXICOLOGY | 1991年 / 4卷 / 03期

关键词：

D O I：

10.1021/tx00021a018

中图分类号：

R914 [药物化学];

学科分类号：

100701 [药物化学];

摘要：

Ab initio molecular orbital calculations at the STO-3G and 3-21G levels were used to clarify the mechanism of mutagenic action of various substituted allyl chlorides. Computed molecular properties were compared with experimental mutagenic potentials of these allylic compounds. In agreement with experiment, the computational results suggest that the primary mechanism of action involves the S(N)1 formation of allylic cations which then react with nucleophilic centers of nuclei acid bases. The usefulness of computed properties in estimating the degree of alkylating activity and mutagenicity was evaluated. In general, stability of the allylic carbocation intermediate and the degree of charge delocalization in the allyl system correlate well with observed mutagenic potentials.

引用

页码：368 / 372

页数：5

共 24 条

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METHODS FOR DETECTING CARCINOGENS AND MUTAGENS WITH SALMONELLA-MAMMALIAN-MICROSOME MUTAGENICITY TEST [J].