Molecular orbital studies on the mechanism of drug-receptor interaction. 2. .beta.-Adrenergic drugs. An approach to explain the role of the aromatic moiety

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Abstract
The role of the aromatic moiety of .beta.-adrenergic drugs in the interaction with the receptor was investigated using the quantum mechanical ab initio method. The structure-activity relationship was essentially discussed by analyzing the electrostatic molecular potential of 3 compounds which constitute meaningful portions of isoproterenol, INPEA [N-isopropyl-1-(p-nitrophenyl)ethanolamine] and doberol, the 1st drug having a stimulating activity and the others a blocking one. The results obtained point out the different roles played in the drug-receptor interaction by the various regions of the drugs and they also show that the aromatic moiety influences both the affinity and the intrinsic activity of the drugs. The spatial correspondence among zones with negative potentials, which are localized on the phenyl substitutents of isoproterenol and INPEA and on the phenyl ring of doberol, could contribute to the affinity. The intrinsic activity of isoproterenol might be associated both with the proton-donor tendency of 1 phenolic OH group and with the wide zone of negative potential which spreads on a large part of the aromatic moiety.

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