Studies on the synthesis and biological evaluation of the metabolite of clausenamide CM₂ and its stereoisomers

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• 作者：XingZhou Li^a ; ^b ; ^{xingzhouli@aliyun.com" class="auth_mail} ; Kangying Lai^a ; KeMei Wu^b ; DaoFei Huang^b ; Liang Huang^b ; ^{huangliang1920@yahoo.cn" class="auth_mail}
• 关键词：Nootropic agents ; Metabolite ; Clausenamide ; Long-term potentiation
• 刊名：European Journal of Medicinal Chemistry
• 出版年：3 March, 2014
• 年：2014
• 卷：74
• 期：Complete
• 页码：736-741
• 全文大小：760 K

文摘

The synthesis and biological evaluation of 5-hydroxy clausenamide (CM₂), one of the major metabolites of clausenamide, and its stereoisomers have been carried out. The absolute configurations of (鈭?- and (+)-CM₂ were assigned as 3S,4S,5S,6S and 3R,4R,5R,6R respectively based on ¹H NMR spectroscopic investigation and their chemical correlation to (鈭?- and (+)-clausenamidone (3). Electrophysiological assay showed that compound (+)-CM₂ and its C₆ epimer (+)-8a had significant effects on synaptic transmission and thus induced the long-term potentiation of the dentate gyrus.