Diastereoselective Synthesis of 3,4-Dihydropyran-3-carboxamides with in Vitro Anti-inflammatory Activity.,ACS Combinatorial Science

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Diastereoselective Synthesis of 3,4-Dihydropyran-3-carboxamides with in Vitro Anti-inflammatory Activity.
ACS Combinatorial Science Pub Date : 2019-09-11 , DOI: 10.1021/acscombsci.9b00050
Li-Yan Zeng ₁ , Baomin Xi ₁ , Kaiqi Huang ₁ , Jingjie Bi ₁ , Lan Wei ₁ , Chun Cai ₂ , Shuwen Liu _{1,

3}

Affiliation

A versatile and economical reaction of diketene (1), aryl amines 2, cyclic 1,3-diketones 3, primary amines 4, and aryl aldehydes 5 was explored to synthesize 3,4-dihydropyran-3-carboxamide derivatives under mild conditions. Three stereogenic centers are generated in the products, and the structure of the major diastereomer of 6{1,1,3,1} was identified by X-ray diffraction and 2D NMR spectroscopy. The scope and limitation investigation provided two series of (2S,3R,4S)-chromene-3-carboxamides in good to excellent yields with high diastereoselectivity. Two products, 6{5,3,1,1} and 6{7,3,1,1}, exhibited in vitro anti-inflammatory activity with significant inhibition of pro-inflammatory cytokine IL-6 and TNF-α expression in lipopolysaccharide (LPS)-treated Raw 264.7 cells.

中文翻译：

具有体外抗炎活性的3,4-二氢吡喃-3-羧酰胺的非对映选择性合成。

探索了在温和条件下，双烯酮（1），芳基胺2，环状1，3-二酮3，伯胺4和芳基醛5的一种通用且经济的反应，可以合成3,4-二氢吡喃-3-甲酰胺衍生物。产品中生成了三个立体异构中心，并通过X射线衍射和2D NMR光谱鉴定了6 {1,1,3,1}的主要非对映异构体的结构。范围和局限性研究提供了两个系列的（2S，3R，4S）-亚甲基-3-羧酰胺，具有良好的收率和优异的非对映选择性。两种产品6 {5,3,1,1}和6 {7,3,1,1}表现出体外抗炎活性，并显着抑制脂多糖中促炎性细胞因子IL-6和TNF-α的表达（LPS）处理的Raw 264.7细胞。

更新日期：2019-09-11

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