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Resolution and adrenergic activities of the optical isomers of 4‐[1‐(1‐Naphthyl)ethyl]‐1 H ‐imidazole
Author(s) -
Hong Seoung S.,
Romstedt Karl J.,
Feller Dennis R.,
Hsu FuLian,
George Clifford,
Cupps Thomas L.,
Lyon Robert A.,
Miller Duane D.
Publication year - 1992
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530040706
Subject(s) - chemistry , imidazole , enantiomer , medetomidine , agonist , resolution (logic) , receptor , stereochemistry , hydrochloride , high performance liquid chromatography , enantiomeric excess , adrenergic receptor , chromatography , organic chemistry , enantioselective synthesis , biochemistry , medicine , heart rate , artificial intelligence , computer science , blood pressure , radiology , catalysis
Recently we synthesized a naphthalene analog of medetomidine, 4‐[1‐(1‐naphthyl)ethyl]‐1 H ‐imidazole hydrochloride (1), and found it to be highly potent in adrenergic systems. The separation of optical isomers of this naphthalene analog was achieved by using the isomers of tartaric acid. The optical purities of the isomers were determined by HPLC using a chiral column. Using X‐ray analysis the (+)‐isomer was determined to have the S absolute configuration. It has been reported that the (+)‐isomer of medetomidine (2) is the most potent enantiomer on α 2 ‐adrenergic receptors. There were both qualitative and quantitative differences in biological activities of the optical isomers of 1 in α 1 ‐ and α 2 ‐adrenergic receptor systems of guinea pig ileum and human platelets. (+)‐(S)‐1, but not (—)‐(R)‐1 was a selective agonist of α 2 ‐mediated responses in ileum whereas (—)‐(R)‐1 was more potent than (+)‐(S)‐1 as an inhibitor of α 2 ‐mediated platelet aggregation. © 1992 Wiley‐Liss, Inc.