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Enantiospecific Synthesis of All Four Stereoisomers of Novel Bicyclic Arylacetamides as k ‐Opioid Agonists
Author(s) -
Long YaQiu,
Mou QiYong,
Qiu DaPing,
Wu RuiQin
Publication year - 2002
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20020201028
Subject(s) - chemistry , bicyclic molecule , stereochemistry , selectivity , amide , ethylenediamine , agonist , pyrrolidine , acetamide , receptor , organic chemistry , catalysis , biochemistry
Conformationally constrained bicyclic derivatives of the potent and selective K‐opioid receptor agonist 2‐(3,4‐dichlorophenyl)‐ N ‐methyl‐ N ‐[(1S)‐1‐phenyl‐2‐(1‐pyrrolidinyl)‐ethlyl] acetamide (3, ICI‐199, 441) were designed to explore the effect of the conformational restriction and stereochemistry of the pharmacophoric ethylenediamine incorporated into the pyrrolidine on the affinity and K‐selectivity. A facile enantiospecific synthetic route was established to afford all four stereoisomers starting from readily available amino adds through mild cyclization and amide formation.