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

7 引文 (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

指紋

Isomers
Saturn
Spectroscopic analysis
Hydrogenation
Rats
Hand
Salts
Nuclear magnetic resonance
Tissue
Crystalline materials
thaliporphine
laurolitsine
aporphine
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Complementary and alternative medicine
  • Molecular Medicine
  • Organic Chemistry
  • Analytical Chemistry
  • Pharmaceutical Science
  • Pharmacology
  • Drug Discovery

引用此文

Chiou, C. M., Lin, C. T., Huang, W. J., Chang, Y. M., Ho, Y. J., Su, M. J., & Lee, S. S. (2013). Semisynthesis and myocardial activity of thaliporphine N-homologues. Journal of Natural Products, 76(3), 405-412. https://doi.org/10.1021/np3007765

Semisynthesis and myocardial activity of thaliporphine N-homologues. / Chiou, Chi Ming; Lin, Chin Ting; Huang, Wei Jang; Chang, Yu Mei; Ho, Yi Jin; Su, Ming Jai; Lee, Shoei Sheng.

於: Journal of Natural Products, 卷 76, 編號 3, 22.03.2013, p. 405-412.

研究成果: 雜誌貢獻文章

Chiou, CM, Lin, CT, Huang, WJ, Chang, YM, Ho, YJ, Su, MJ & Lee, SS 2013, 'Semisynthesis and myocardial activity of thaliporphine N-homologues', Journal of Natural Products, 卷 76, 編號 3, 頁 405-412. https://doi.org/10.1021/np3007765
Chiou, Chi Ming ; Lin, Chin Ting ; Huang, Wei Jang ; Chang, Yu Mei ; Ho, Yi Jin ; Su, Ming Jai ; Lee, Shoei Sheng. / Semisynthesis and myocardial activity of thaliporphine N-homologues. 於: Journal of Natural Products. 2013 ; 卷 76, 編號 3. 頁 405-412.
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