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• W2088845157 abstract "Conformational energy calculations using the Molecular Mechanics II (MM2) program have been performed on 2-aminotetrahydronaphthalene (ATN) and 2-aminoindan derivatives which are active or inactive at dopamine receptors. The results were used to test a stereochemical and conformational model previously proposed for dopaminergic activity. The conformer predicted to be optimal for agonist activity was found to have relatively low energy (<1.5 kcal/mol) for all of the agonists examined. The model successfully: (1) explained the relative activity or inactivity of compounds such as cis- and trans-1-methyl-5-hydroxyl ATN derivatives and the corresponding cis- and trans-octohydrobenzo[f]quinolines; (2) predicted the more potent antipode of 2-aminoindan dopaminergic agonists; and (3) explained the structure-activity peculiarities of 3-(3-hydroxyphenyl)-N-alkylpiperidines in which the potency is increased for (3S)-isomers and decreased for (3R)-isomers when the N-alkyl group is greater than propyl. Predictions of postsynaptic dopaminergic antagonism were also made for some of the compounds. In agreement with previous conclusions, the inactivity of ATN derivatives with a 2-methyl or 5-propyl group was attributed to steric interference at the receptor since those groups did not have a significant conformational effect on the receptor ligand." @default.
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• W2088845157 date "1987-07-01" @default.
• W2088845157 modified "2023-09-26" @default.
• W2088845157 title "A Stereochemical and Conformational Model of Dopaminergic Agonist and Antagonist Activity: Further Evaluation" @default.
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• W2088845157 doi "https://doi.org/10.1002/jps.2600760715" @default.
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