Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 15, Issue 16, Pages 5417-5423Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2007.05.059
Keywords
tetrahydroisoquinoline; microwave-assisted synthesis; anticonvulsant; AMPA-antagonist; molecular modeling; enantiomeric resolution; X-ray crystal structure
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Recently we identified (R,S)-2-acetyl-1-(4'-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (6) as a potent non-competitive AMPA receptor antagonist able to prevent epileptic seizures. We report here the optimized synthesis of compound 6, its resolution by chiral preparative HPLC, and the absolute configuration of (R)-enantiomer established by X-ray diffractometry. The biological tests of the single enantiomers revealed that higher anticonvulsant and antagonistic effects reside in (R)-enantiomer as also suggested by molecular modeling studies. (c) 2007 Elsevier Ltd. All rights reserved.
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