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

Author:

Li Ying1,Yu Pei1,Shi Hefei1,Yang Tingting1,Feng Chuanling1,He Yujiao1,Dong Hongbo1

Affiliation:

1. Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, China

Abstract

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.

Funder

National Natural Science Foundation of China

Open Research Fund of the Key Laboratory of Coarse Cereal Processing of the Ministry of Agriculture and Rural Affairs

Publisher

Bentham Science Publishers Ltd.

Subject

Organic Chemistry,Biochemistry

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