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Correlation of mutagenicity of 1,1‐dimethyl‐3‐(X‐phenyl)‐triazenes with molecular orbital energies and hydrophobicity
Author(s) -
Shusterman Alan J.,
Johnson A. Sherwood,
Hansch Corwin
Publication year - 1989
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560360105
Subject(s) - mndo , chemistry , triazene , homo/lumo , computational chemistry , molecular orbital , electronic structure , ames test , density functional theory , molecule , stereochemistry , organic chemistry , biology , salmonella , bacteria , genetics
A set of 18 aryltriazenes and the antitumor drug DTIC, whose mutagenicity has been determined in the Ames test, has been studied using octanol‐water partition coefficients ( P ) as a measure of relative hydrophobicity and MNDO molecular orbital energies and electron distributions to account for variation in their electronic characteristics. A good structure‐activity relationship was found using log P in combination with either ε HOMO , or q HOMO , where the latter is defined as the HOMO electron density on N 1 of the triazene. The dependence of mutagenicity on hydrophobicity is similar to what had been found earlier by Venger, Hansch, Hatheway, and Amrein [4] for the aryltriazenes alone using σ + as a descriptor of electronic characteristics. A consistent role for electronic factors is found using σ + , ε HOMO and q HOMO , namely, increased mutagenicity is associated with structural variations that increase the electron donating ability of the triazenes.