dc.contributor.author | Amakali, Klaudia T. | |
dc.contributor.author | Legoabe, Lesetja J. | |
dc.contributor.author | Petzer, Anél | |
dc.contributor.author | Petzer, Jacobus P. | |
dc.date.accessioned | 2018-11-21T13:15:06Z | |
dc.date.available | 2018-11-21T13:15:06Z | |
dc.date.issued | 2018 | |
dc.identifier.citation | Amakali, K.T. et al. 2018. Synthesis and in vitro evaluation of 2-heteroarylidene-1-tetralone derivatives as monoamine oxidase inhibitors. Drug research, 68(12):687-695. [https://doi.org/10.1055/a-0620-8309] | en_US |
dc.identifier.issn | 2194-9379 (Online) | |
dc.identifier.uri | http://hdl.handle.net/10394/31725 | |
dc.identifier.uri | https://www.thieme-connect.com/products/ejournals/abstract/10.1055/a-0620-8309 | |
dc.identifier.uri | https://doi.org/10.1055/a-0620-8309 | |
dc.description.abstract | The present study investigates the human monoamine oxidase (MAO) inhibition properties of a series of twelve 2-heteroarylidene-1-tetralone derivatives. Also included are related cyclohexylmethylidene, cyclopentylmethylidene and benzylidene substituted 1-tetralones. These compounds are related to the 2-benzylidene-1-indanone class of compounds which has previously been shown to inhibit the MAOs, with specificity for the MAO-B isoform. The target compounds were synthesised by the Claisen-Schmidt condensation between 7-methoxy-1-tetralone or 1-tetralone, and various aldehydes, under acid (hydrochloric acid) or base (potassium hydroxide) catalysis. The results of the MAO inhibition studies showed that the 2-heteroarylidene-1-tetralone and related derivatives are in most instances more selective inhibitors of the MAO-B isoform compared to MAO-A. (2E)-2-Benzylidene-7-methoxy-3,4-dihydronaphthalen-1(2 H)-one (IC50=0.707 μM) was found to be the most potent MAO-B inhibitor, while the most potent MAO-A inhibitor was (2E)-2-[(2-chloropyridin-3-yl)methylidene]-7-methoxy-3,4-dihydronaphthalen-1(2 H)-one (IC50=1.37 μM). The effect of the heteroaromatic substituent on MAO-B inhibition activity, in decreasing order was found to be: cyclohexyl, phenyl>thiophene>pyridine, furane, pyrrole, cyclopentyl. This study concludes that, although some 2-heteroarylidene-1-tetralone derivatives are good potency MAO inhibitors, in general their inhibition potencies, particularly for MAO-B, are lower than structurally related chalcones and 1-indanone derivatives that were previously studied | en_US |
dc.language.iso | en | en_US |
dc.publisher | Thieme | en_US |
dc.subject | Monoamine oxidase | en_US |
dc.subject | Inhibition | en_US |
dc.subject | Parkinson’s disease | en_US |
dc.subject | Alzheimer’s disease | en_US |
dc.subject | Heteroarylidene-1-tetralone | en_US |
dc.subject | 2-Benzylidene-1-tetralone | en_US |
dc.title | Synthesis and in vitro evaluation of 2-heteroarylidene-1-tetralone derivatives as monoamine oxidase inhibitors | en_US |
dc.type | Article | en_US |
dc.contributor.researchID | 12902608 - Legoabe, Lesetja Jan | |
dc.contributor.researchID | 10727388 - Petzer, Jacobus Petrus | |
dc.contributor.researchID | 12264954 - Petzer, Anél | |