Semisynthesis and myocardial activity of thaliporphine N-homologues

Chi Ming Chiou, Chin Ting Lin, Wei Jang Huang, Yu Mei Chang, Yi Jin Ho, Ming Jai Su, Shoei Sheng Lee

研究成果: 雜誌貢獻文章同行評審

8 引文 斯高帕斯(Scopus)

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
頁(從 - 到)405-412
頁數8
期刊Journal of Natural Products
76
發行號3
DOIs
出版狀態已發佈 - 三月 22 2013

ASJC Scopus subject areas

  • 補充和替代醫學
  • 分子醫學
  • 有機化學
  • 分析化學
  • 藥學科學
  • 藥理
  • 藥物發現

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