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Issue 3, 2018
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Enantioselective synthesis of novel pyrano[3,2-c]chromene derivatives as AChE inhibitors via an organocatalytic domino reaction

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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.

Graphical abstract: Enantioselective synthesis of novel pyrano[3,2-c]chromene derivatives as AChE inhibitors via an organocatalytic domino reaction

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Publication details

The article was received on 15 Nov 2017, accepted on 14 Dec 2017 and first published on 14 Dec 2017


Article type: Paper
DOI: 10.1039/C7OB02794J
Citation: Org. Biomol. Chem., 2018,16, 472-479
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    Enantioselective synthesis of novel pyrano[3,2-c]chromene derivatives as AChE inhibitors via an organocatalytic domino reaction

    J. Zheng, M. He, B. Xie, L. Yang, Z. Hu, H. Zhou and C. Dong, Org. Biomol. Chem., 2018, 16, 472
    DOI: 10.1039/C7OB02794J

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