Synthesis of N-substituted 4-(4-hydroxyphenyl) piperidines, 4-(4-hydroxybenzyl) piperidines, and (±)-3-(4-hydroxyphenyl) pyrrolidines: selective antagonists at the 1A/ …

…, M Tran, ER Whittemore, RM Woodward…

Index: Tamiz, Amir P.; Whittemore, Edward R.; Schelkun, Robert M.; Yuen, Po-Wai; Woodward, Richard M.; Cai, Sui-Xiong; Weber, Eckard; Keana, John F. W. Bioorganic and Medicinal Chemistry Letters, 1998 , vol. 8, # 2 p. 199 - 200

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Citation Number: 46

Abstract

Antagonists at the 1a/2B subtype of the NMDA receptor (NR1a/2B) are typically small molecules that consist of a 4-benzyl-or a 4-phenylpiperidine with an ω-phenylalkyl substituent on the heterocyclic nitrogen. Many of these antagonists, for example ifenprodil (1), incorporate a 4-hydroxy substituent on the ω-phenyl group. In this study, the position of this 4-hydroxy substituent was transferred from the ω-phenyl group to the benzyl or phenyl ...