ISSN:
0020-7608
Keywords:
Computational Chemistry and Molecular Modeling
;
Atomic, Molecular and Optical Physics
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 εHOMO, or qHOMO, where the latter is defined as the HOMO electron density on N1 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+, εHOMO and qHOMO, namely, increased mutagenicity is associated with structural variations that increase the electron donating ability of the triazenes.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/qua.560360105
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