Enantioselective synthesis of novel pyrano[3,2-c]chromene derivatives as AChE inhibitors via an organocatalytic domino reaction
Literature Information
Publication Date
2017-12-14
DOI
10.1039/C7OB02794J
Impact Factor
3.876
Authors
Jie Zheng, Ming He, Baohua Xie, Lu Yang, Zhiye Hu, Hai-Bing Zhou
View Original
Abstract
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.
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