Lee, Fong-Kai and Krishnan, Premanand and Muhamad, Azira and Low, Yun-Yee and Kam, Toh-Seok and Ting, Kang-Nee and Lim, Kuan-Hon (2022) Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B. Natural Product Research, 36 (15). pp. 3972-3978. ISSN 1478-6419, DOI https://doi.org/10.1080/14786419.2021.1903005.
Full text not available from this repository.Abstract
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.
| Item Type: | Article |
|---|---|
| Funders: | MOHE Malaysia (Grant No: FRGS/1/2017/STG01/UNIM/02/3 & FRGS/1/2017/SKK10/UNIM/01/1), Malaysia Toray Science Foundation (Grant No: TML-CA/17.195(17/G62)) |
| Uncontrolled Keywords: | Ficus schwarzii; Schwarzinicine; Phenethylamine; Alkaloid; Synthesis; Vasorelaxation |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 20 Oct 2023 04:48 |
| Last Modified: | 20 Oct 2023 04:48 |
| URI: | http://eprints.um.edu.my/id/eprint/41830 |
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