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3-Coumaranone derivatives as inhibitors of monoamine oxidase

Authors Van Dyk A, Petzer J, Petzer A, Legoabe L

Received 5 June 2015

Accepted for publication 28 July 2015

Published 3 October 2015 Volume 2015:9 Pages 5479—5489


Checked for plagiarism Yes

Review by Single anonymous peer review

Peer reviewer comments 3

Editor who approved publication: Prof. Dr. Wei Duan

Adriaan S Van Dyk,1,2 Jacobus P Petzer,1,2 Anél Petzer,1 Lesetja J Legoabe1

1Centre of Excellence for Pharmaceutical Sciences, 2Pharmaceutical Chemistry, School of Pharmacy, North-West University, Potchefstroom, South Africa

Abstract: The present study examines the monoamine oxidase (MAO) inhibitory properties of a series of 20 3-coumaranone [benzofuran-3(2H)-one] derivatives. The 3-coumaranone derivatives are structurally related to series of α-tetralone and 1-indanone derivatives, which have recently been shown to potently inhibit MAO, with selectivity for MAO-B (in preference to the MAO-A isoform). 3-Coumaranones are similarly found to selectively inhibit human MAO-B with half-maximal inhibitory concentration (IC50) values of 0.004–1.05 µM. Nine compounds exhibited IC50<0.05 µM for the inhibition of MAO-B. For the inhibition of human MAO-A, IC50 values ranged from 0.586 to >100 µM, with only one compound possessing an IC50<1 µM. For selected 3-coumaranone derivatives, it is established that MAO-A and MAO-B inhibition are reversible since dialysis of enzyme–inhibitor mixtures almost completely restores enzyme activity. On the basis of the selectivity profiles and potent action, it may be concluded that the 3-coumaranone derivatives are suitable leads for the development of selective MAO-B inhibitors as potential treatment for disorders such as Parkinson’s disease and Alzheimer’s disease.

Keywords: benzofuran-3(2H)-one, MAO, inhibition, reversible, competitive, Parkinson’s disease

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