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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Total Syntheses and Anti-inflammatory Evaluations of Karanjin and its Natural Analogues

Author(s): Ying Li, Pei Yu, Hefei Shi, Tingting Yang, Chuanling Feng, Yujiao He* and Hongbo Dong*

Volume 20, Issue 6, 2023

Published on: 27 January, 2023

Page: [562 - 567] Pages: 6

DOI: 10.2174/1570178620666221230145816

Price: $65

Abstract

Karanjin (1) is a natural furanoflavonol derivative isolated from seeds of Pongamia pinnata (L.) Pierre. In this paper, we have accomplished a concise total synthesis of karanjin (1) as well as its natural analogues pongapinnol D (2), 3-hydroxy-6-methoxy-2-phenyl-4H-furo[2,3-h]-1-benzopyran- 4-one (3) and 3,6-dimethoxy-2-phenyl-4H-furo[2,3-h]chromen-4-one (4). One-pot aerobic oxidation was the key step to afford the flavonol framework under mild conditions. The anti-inflammatory properties of synthesized 1–4 were determined against NO production in the LPS-stimulated RAW264.7 cells.

Keywords: Karanjin (1), furanoflavonols, cytokine, rheumatic arthritis, Baker-Venkataraman, RAW264.7 macrophages.

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