Reactivity prediction in aza-Michael additions without transition state calculations: the Ames test for mutagenicity

Animal testing remains a contentious ethical issue in predictive toxicology. Thus, a fast, versatile, low-cost quantum chemical model is presented for predicting the risk of Ames mutagenicity in a series of 1,4 Michael acceptor type compounds. This framework eliminates the need for transition state...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-11, Vol.56 (88), p.13661-13664
Main Authors: Townsend, Piers A, Grayson, Matthew N
Format: Article
Language:English
Subjects:
Ames test
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Density Functional Theory
Models, Chemical
Molecular Structure
Mutagenicity
Mutagens - chemistry
Mutagens - pharmacology
Quantitative Structure-Activity Relationship
Quantum chemistry
Salmonella typhimurium - drug effects
Toxicology
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Summary:Animal testing remains a contentious ethical issue in predictive toxicology. Thus, a fast, versatile, low-cost quantum chemical model is presented for predicting the risk of Ames mutagenicity in a series of 1,4 Michael acceptor type compounds. This framework eliminates the need for transition state calculations, and uses an intermediate structure to probe the reactivity of aza-Michael acceptors. This model can be used in a variety of settings e.g. , the design of targeted covalent inhibitors and polyketide biosyntheses. This work demonstrates a novel method for aza-Michael reactivity prediction using easily calculable intermediate structures instead of time-consuming transition states.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc05681b