Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B

被引：8

作者：

Lee, Fong-Kai ^{[1
]}

Krishnan, Premanand ^{[1
]}

Muhamad, Azira ^{[2
]}

Low, Yun-Yee ^{[3
]}

Kam, Toh-Seok ^{[3
]}

Ting, Kang-Nee ^{[1
]}

Lim, Kuan-Hon ^{[1
]}

机构：

[1] Univ Nottingham Malaysia, Sch Pharm, Semenyih, Selangor, Malaysia

[2] Malaysia Genome Inst, Kajang, Selangor, Malaysia

[3] Univ Malaya, Fac Sci, Dept Chem, Kuala Lumpur, Malaysia

来源：

NATURAL PRODUCT RESEARCH | 2022年 / 36卷 / 15期

关键词：

Ficus schwarzii; schwarzinicine; phenethylamine; alkaloid; synthesis; vasorelaxation;

D O I：

10.1080/14786419.2021.1903005

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A concise synthesis of the 1,4-diarylbutanoid-phenethylamine alkaloids, schwarzinicines A (1) and B (2), recently isolated from Ficus schwarzii, is reported. Key steps include a Claisen condensation to assemble the 1,4-diaryl-2-butanone intermediate, followed by a reductive amination to furnish the core skeleton of the target compounds. The overall synthetic yields of 1 and 2 were 9.1% and 3.5%, respectively. Synthetic (-)-1, (+)-1 and (+/-)-1 exhibited comparable vasorelaxation as natural schwarzinicine A on rat isolated aortic rings, suggesting that the observed vasorelaxant effects were not influenced by the chirality at C-2.

引用

页码：3972 / 3978

页数：7

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