Synthesis, anti-GABA activity and preferred conformation of bicuculline and norbicuculline enantiomers

…, ND Luyen, G Dörnyei, E Gács-Baitz, M Simonyi…

文献索引：Kardos; Blandl; Luyen; Doernyei; Gacs-Baitz; Simonyi; Cash; Blasko; Szantay European Journal of Medicinal Chemistry, 1996 , vol. 31, # 10 p. 761 - 765

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被引用次数: 9

摘要

Synthesis of erythro-(±)-[1SR, 9RS]-norbicuculline and threo-(±)-[1SR, 9SR]-noradlumidine from piperonal was performed using Bischler-Napieralski cyclization as a key step. Resolution gave rise to (+)-[1S, 9R]-norbicuculline ([1S, 9R] norBIC) and (−)-[1R, 9S]- norbicuculline ([1R, 9S] norBIC) in> 99.5% enantiomeric purity. Bicuculline enantiomers were readily obtained by methylation of the latter products.[1S, 9R] BIC was about 70 ...