A Marked Change of Receptor Affinity of the 2-Methyl-5-(3-hydroxyphenyl) morphans upon Attachment of an (E)-8-Benzylidene Moiety: Synthesis and Evaluation of a …

…, JL Flippen-Anderson, RB Rothman, H Xu…

Index: Bertha, Craig M.; Mattson, Mariena V.; Flippen-Anderson, Judith L.; Rothman, Richard B.; Xu, Heng; et al. Journal of Medicinal Chemistry, 1994 , vol. 37, # 19 p. 3163 - 3170

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Citation Number: 18

Abstract

Methods Chemical Synthesis. The racemic compound 2 was prepared by following a reported literature procedure. 22 The benzylidene moiety of racemic 3 was incorporated using Claisen-Schmidt conditions (85%). Under the reaction conditions used, one predominant isomer was formed [(E)-81 out of four possible isomers. Compound 3 was demethylated using BBr3, forming racemic 5. Compound 6 was prepared by a Claisen- ...