Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B

Authors

• Fong-Kai Lee
• Premanand Krishnan
• Azira Muhamad
• Yun-Yee LowFollow
• Toh-Seok KamFollow
• Kang-Nee Ting
• Kuan-Hon Lim

Document Type

Article

Publication Date

8-1-2022

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.

Keywords

Ficus schwarzii, Schwarzinicine, Phenethylamine, Alkaloid, Synthesis, Vasorelaxation

Publication Title

Natural Product Research

Recommended Citation

Lee, Fong-Kai; Krishnan, Premanand; Muhamad, Azira; Low, Yun-Yee; Kam, Toh-Seok; Ting, Kang-Nee; and Lim, Kuan-Hon, "Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B" (2022). Research Publications (2021 to 2025). 947.
https://knova.um.edu.my/research_publications_2021_2025/947

Divisions

CHEMISTRY

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))

Volume

36

Issue

15

Publisher

Taylor & Francis

Publisher Location

2-4 PARK SQUARE, MILTON PARK, ABINGDON OR14 4RN, OXON, ENGLAND