title: Studies on the synthesis and biological evaluation of the metabolite of clausenamide CM₂ and its stereoisomers.
abstract: 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 (-)- and (+)-CM₂ were assigned as 3S,4S,5S,6S and 3R,4R,5R,6R respectively based on (1)H NMR spectroscopic investigation and their chemical correlation to (-)- 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.
authors.affiliation: Beijing Institute of Pharmacology and Toxicology, 27 Taiping Rd., Beijing 100850, China; Institute of Materia Medica, Chinese Academy of Medical Sciences, 1 Xian Nong Tan St., Beijing 100050, China. Electronic address: xingzhouli@aliyun.com.
authors.forename: XingZhou
authors.initials: X
authors.lastname: Li
authors.affiliation: Beijing Institute of Pharmacology and Toxicology, 27 Taiping Rd., Beijing 100850, China.
authors.forename: Kangying
authors.initials: K
authors.lastname: Lai
authors.affiliation: Institute of Materia Medica, Chinese Academy of Medical Sciences, 1 Xian Nong Tan St., Beijing 100050, China.
authors.forename: KeMei
authors.initials: K
authors.lastname: Wu
authors.affiliation: Institute of Materia Medica, Chinese Academy of Medical Sciences, 1 Xian Nong Tan St., Beijing 100050, China.
authors.forename: DaoFei
authors.initials: D
authors.lastname: Huang
authors.affiliation: Institute of Materia Medica, Chinese Academy of Medical Sciences, 1 Xian Nong Tan St., Beijing 100050, China. Electronic address: huangliang1920@yahoo.cn.
authors.forename: Liang
authors.initials: L
authors.lastname: Huang
mesh_terms: D000818:Animals; D018891:Dentate Gyrus / Q000187:drug effects; D004353:Drug Evaluation, Preclinical; D005260:Female; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017705:Lignans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017774:Long-Term Potentiation / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry / Q000379:methods; D017207:Rats, Sprague-Dawley; D013237:Stereoisomerism; D009435:Synaptic Transmission / Q000187:drug effects
chemical_list: D007769:Lactams; D017705:Lignans; C053048:clausenamide
keywords: Clausenamide; Long-term potentiation; Metabolite; Nootropic agents