Syntheses of Minutuminolate and Related Coumarin Natural Products and Evaluation of Their TNF-α Inhibitory Activities

被引：0
|
作者：
Choo, Malcolm Zheng Yuan [1 ]
Khaw, Lachelle Wei Ting [1 ]
Chai, Christina Li Lin [1 ]
机构：
[1] Natl Univ Singapore, Dept Pharm, Singapore 117543, Singapore
来源：
ACS OMEGA | 2023年 / 8卷 / 44期
关键词：
DERIVATIVES; CHEMISTRY; SCAFFOLD; ACCESS;
D O I：
10.1021/acsomega.3c06361
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The concise syntheses of the coumarin natural product, minutuminolate (1), and its related natural products, 7-methoxy-8-(2-acetoxy-3-methyl-1-oxobut-2-enyl) coumarin (2) and muralatin I (3), were accomplished for the first time in 4-5 steps from the commercially available umbelliferone. The key step involves a palladium-catalyzed oxidative rearrangement reaction to assemble the alpha-acyloxyenone moiety in 1 and 2. The incorporation of this functionality enables the successful synthesis of coumarin 3 through an acidic hydrolysis reaction. The anti-inflammatory activities of the compounds were also evaluated against tumor necrosis factor-alpha production in lipopolysaccharides-stimulated RAW264.7 cells. Our developed synthetic route will facilitate the development of analogues and derivatives of 1-3 with potent anti-inflammatory activities.
引用
收藏
页码：41785 / 41791
页数：7
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