Citation: . Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2, 3-dihydro-1-benzofuran-3-one derivatives[J]. Chinese Chemical Letters, ;2017, 28(7): 1528-1532. doi: 10.1016/j.cclet.2017.02.009 shu

Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2, 3-dihydro-1-benzofuran-3-one derivatives

Received Date: 2 November 2016
Revised Date: 26 December 2016
Accepted Date: 17 February 2017
Available Online: 20 July 2017

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A series of 2-(arylmethylidene)-2, 3-dihydro-1-benzofuran-3-one derivatives (aurones, 1-20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1-5, 7-17, 19) were found to be selective towards hMAO-B, while two were non-selective (6 and 20) and one (18) selective towards hMAO-A. Compound 17 (Ki=0.10±0.01 μmol/L) was found to be equally potent and selective towards hMAO-B, when compared with the standard drug Selegiline (Ki=0.12±0.01 μmol/L). Nature and position of substitution in aryl ring at 2nd position of benzofuranone influences hMAO-B inhibitory potency, while their structural bulkiness influences selectivity between hMAO-A and hMAO-B. Molecular docking simulation was also carried out to understand the interaction of inhibitor with the enzyme at molecular level, and we found the docking results were in good agreement with the experimental values. Comparison of the activity profile of the aurones with their corresponding flavones reported earlier by our group revealed that there exists no difference in potency as well as selectivity.
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