Enantioselective synthesis of novel pyrano[3,2-c]chromene derivatives as AChE inhibitors via an organocatalytic domino reaction†,Organic & Biomolecular Chemistry

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Enantioselective synthesis of novel pyrano[3,2-c]chromene derivatives as AChE inhibitors via an organocatalytic domino reaction†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-12-14 00:00:00 , DOI: 10.1039/c7ob02794j
Jie Zheng _{1,

2,

3,

4,

5} , Ming He _{1,

2,

3,

4,

5} , Baohua Xie _{1,

2,

3,

4,

5} , Lu Yang _{1,

2,

3,

4,

5} , Zhiye Hu _{1,

2,

3,

4,

5} , Hai-Bing Zhou _{1,

2,

3,

4,

5} , Chune Dong _{1,

2,

3,

4,

5}

Affiliation

A series of optically active pyrano[3,2-c]chromenes have been synthesized through an asymmetric domino reaction of 4-hydroxy-2H-chromen-2-ones with malononitriles. The targeted molecules were obtained in excellent yields and enantioselectivities (up to 94% yield, 99% ee). The AChE inhibitory activity studies revealed that compounds 4n (IC₅₀ = 21.3 μM) and 4p (IC₅₀ = 19.2 μM) displayed potent acetylcholinesterase inhibition. In most cases, the S-enantiomers were superior to the corresponding R-enantiomers. Moreover, molecular modelling provides a practical method for understanding the enantioselective discrimination of AChE with these kinds of compounds.

中文翻译：

通过有机催化多米诺反应对作为AChE抑制剂的吡喃并[3,2- c ]色烯衍生物进行对映选择性合成†

通过4-羟基-2 H-苯甲基-2-酮与丙二腈的不对称多米诺反应，合成了一系列旋光的吡喃并[3,2- c ]色烯。以优异的收率和对映选择性（高达94％的收率，99％ee）获得了目标分子。AChE抑制活性研究表明，化合物4n（IC ₅₀ = 21.3μM）和4p（IC ₅₀ = 19.2μM）显示出有效的乙酰胆碱酯酶抑制作用。在大多数情况下，S-对映异构体优于相应的R-对映体。此外，分子建模为理解这类化合物对AChE的对映选择性提供了一种实用的方法。

更新日期：2017-12-14

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