Conformational restriction of the phenylalanine residue in a cyclic opioid peptide analog: effects on receptor selectivity and stereospecificity

…, C Lemieux, NN Chung, BJ Marsden…

Index: Schiller; Weltrowska; Nguyen; Lemieux; Chung; Marsden; Wilkes Journal of Medicinal Chemistry, 1991 , vol. 34, # 10 p. 3125 - 3132

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Citation Number: 100

Abstract

In an effort to determine the effect of side chain conformational restriction on opioid receptor selectivity, the cyclic phenylalanine analogues 2-aminoindan-2-carboxylic acid (Aic), 2- aminotetralin-2-carboxylic acid (Atc), and tetra-hydroisoquinoline-3-carboxylic acid (Tic) were substituted for Phe in the potent cyclic opioid peptide analogue H-Tyr-~-Orn-Phe-Glu- NH~, which lacks significant opioid receptor selectivity. Compounds were tested in p-and ...