Conformationally defined adrenergic agents. 1. Design and synthesis of novel. alpha. 2-selective adrenergic agents: electrostatic repulsion based conformational …

JF DeBernardis, DJ Kerkman, M Winn…

Index: DeBernardis; Kerkman; Winn; Bush; Arendsen; McClellan; Kyncl; Basha Journal of Medicinal Chemistry, 1985 , vol. 28, # 10 p. 1398 - 1404

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Citation Number: 44

Abstract

A previous report of the adrenergic selectivity of 2-and 6-fluoronorepinephrine prompted us to formulate a hypothesis that accounted for this selectivity on the basis of a conformational preference induced by electrostatic repulsion between the aromatic fluorine atom and the side-chain hydroxyl group. A series of nitrogen-substituted catechol (aminomethyl) benzocyclobutenes, indanes, tetralins, and benzocycloheptenes were prepared, and ...