6533b836fe1ef96bd12a1405
RESEARCH PRODUCT
Prediction of properties of chiral compounds by molecular topology
J.v. De Julián-ortizRamón García-domenechJorge GalvezC. De Gregorio AlapontI. Rı́os-santamarinasubject
inorganic chemicalsStereochemistryIn Vitro TechniquesMain diagonalStructure-Activity RelationshipMatrix (mathematics)PiperidinesComputational chemistryMaterials ChemistryAnimalsHypnotics and SedativesReceptors sigmaheterocyclic compoundsPhysical and Theoretical ChemistrySpectroscopyGroup (mathematics)Chemistryorganic chemicalsStereoisomerismComputer Graphics and Computer-Aided DesignDopamine D2 Receptor AntagonistsCharacter (mathematics)Models ChemicalDrug DesignCentral Nervous System StimulantsMolecular topologyEnantiomerSymmetry (geometry)Chirality (chemistry)description
Abstract 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 (IC50) values of the D2 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1998-10-23 | Journal of Molecular Graphics and Modelling |