Synthesis of 1??(m??Hydroxybenzyl)??Substituted 1, 2, 3, 4??Tetrahydroisoquinoline??3??carboxylic Acid Derivatives as Opioid Peptide Mimetics− Unexpected Amide Bond …

…, S Van Cauwenberghe, D Tourwé

Index: Mannekens, Els; Crisma, Marco; Van Cauwenberghe, Sylvia; Tourwe, Dirk European Journal of Organic Chemistry, 2003 , # 17 p. 3300 - 3307

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Citation Number: 6

Abstract

Abstract N-Glycyl-(1R, 3S)-1-(m-hydroxybenzyl)-1, 2, 3, 4-tetrahydroisoquinoline-3- carboxylic acid (Tic) was prepared as a Tyr-Tic dipeptide mimetic for exploration of its potential as a delta opioid receptor selective ligand. The compound was successfully obtained by a stereoselective synthesis starting from L-Tic. In the course of the reactions, unusual peptide bond cleavages were observed under mild conditions, and reaction ...