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Prediction of properties of chiral compounds by molecular topology

A common assumption in chemistry is that chiral behavior is associated with 3-D geometry. However, chiral information is related to symmetry, which allows the topological handling of chiral atoms by weighted graphs and the calculation of new descriptors that give a weight to the corresponding entry...

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Bibliographic Details
Published in:Journal of molecular graphics & modelling 1998-02, Vol.16 (1), p.14-18
Main Authors: de Julián-Ortiz, J.V., de Gregorio Alapont, C., Rı́os-Santamarina, I., Garcı́a-Doménech, R., Gálvez, J.
Format: Article
Language:English
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Summary:A common assumption in chemistry is that chiral behavior is associated with 3-D geometry. However, chiral information is related to symmetry, which allows the topological handling of chiral atoms by weighted graphs and the calculation of new descriptors that give a weight to the corresponding entry in the main diagonal of the topological matrix. In this study, it is demonstrated that, operating in this way, chiral topological indices are obtained that can differentiate the pharmacological activity between pairs of enantiomers. The 50% inhibitory concentration (IC 50) values of the D 2 dopamine receptor and the σ receptor for a group of 3-hydroxy phenyl piperidines are specifically predicted. Moreover, the sedative character of a group of chiral barbiturates can be identified.
ISSN:1093-3263
1873-4243
DOI:10.1016/S1093-3263(98)00013-8