摘要
The N-homologues and optical isomers of thaliporphine (5a), a potent antiarrhythmic agent, were prepared starting from laurolitsine (1), an abundant aporphine present in Phoebe formosana. Treating N-propylnorglaucine with 90% H2SO4 yielded one additional product, an 11-sulfonyl-1,11-anhydroaporphine. Reaction of N-formylnorglaucine (3a) with 90% H2SO4, however, yielded the 9-sulfonyl-seco product as a major product. Treatment of 3a with 98% H2SO4 yielded pancordine (10), which, upon catalytic hydrogenation, yielded (±)-wilsonirine. 1H NMR spectroscopic analysis was applied successfully to monitor the optical purity of the crystalline salt while undertaking optical resolution. Thaliporphine (5a) was demonstrated to possess better positive inotropic and less negative chronotropic effects than the left-hand optical isomer and showed the best activity on rat cardiac tissue among the N-homologues prepared.
原文 | 英語 |
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頁(從 - 到) | 405-412 |
頁數 | 8 |
期刊 | Journal of Natural Products |
卷 | 76 |
發行號 | 3 |
DOIs | |
出版狀態 | 已發佈 - 3月 22 2013 |
ASJC Scopus subject areas
- 藥物發現
- 分析化學
- 分子醫學
- 補充和替代醫學
- 藥理
- 藥學科學
- 有機化學