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

…, AP Tamiz, M Acosta-Burruel, S Hong-Bae…

Index: Guzikowski, Anthony P.; Tamiz, Amir P.; Acosta-Burruel, Manuel; Hong-Bae, Soo; Cai, Sui Xiong; Hawkinson, Jon E.; Keana, John F. W.; Kesten, Suzanne R.; Shipp, Christina T.; Tran, Minhtam; Whittemore, Edward R.; Woodward, Richard M.; Wright, Jon L.; Zhou, Zhang-Lin Journal of Medicinal Chemistry, 2000 , vol. 43, # 5 p. 984 - 994

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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 ...