Synthesis of 1-(m-Hydroxybenzyl)-Substituted 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid Derivatives as Opioid Peptide Mimetics - Unexpected Amide Bond Cleavages under Mild Conditions

摘要

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 wre observed under mild conditions, and reaction mechanism have been proposed.