کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1395375 | 1501123 | 2015 | 13 صفحه PDF | دانلود رایگان |
• A series of quinoxalinyl hydrazones and hydrazides were synthesized.
• The compounds were evaluated in vitro as inhibitors of the two monoamine oxidase isoforms, MAO-A and MAO-B.
• Most of the compounds showed a potent and selective MAO-A inhibitory activity where 4e and 9g were the most potent derivatives.
• Molecular modeling studies were performed to rationalize the recognition of all inhibitors with respect to hMAO-A.
In this investigation, we searched for novel MAO-A inhibitors using a 3-benzylquinoxaline scaffold based on our earlier findings. Series of N′-(3-benzylquinoxalin-2-yl)acetohydrazide, 4a, N′-(3-benzylquinoxalin-2-yl)benzohydrazide derivatives 4b–f, N′-[2-(3-benzyl-2-oxoquinoxalin-1(2H)-yl)acetyl]benzohydrazide derivatives 7a–d, (9H-fluoren-9-yl)methyl 1-[2-(2-(3-benzyl-2-oxoquinoxalin-1(2H)-yl)acetyl)-hydrazinyl]-2-ylcarbamate derivatives 8a–c, 2-(3-benzyl-2-oxoquinoxalin-1(2H)-yl)-N′-benzylidene acetohydrazide derivatives 9a–h, and ethyl 2-(3-benzyl-2-oxoquinoxalin-1(2H)-yl)acetate derivatives 10a–e were synthesized and evaluated in vitro as inhibitors of the two monoamine oxidase isoforms, MAO-A and MAO-B. Most of the compounds showed a selective MAO-A inhibitory activity in the nanomolar or low micromolar range. Compounds 4e and 9g were the most potent derivatives with high MAO-A selectivity and their molecular docking studies were performed in order to rationalize the obtained biological result.
Series of 3-benzylquinoxalinyl hydrazones and hydrazides were synthesized and were evaluated in vitro as inhibitors of the two monoamine oxidase isoforms, MAO-A and MAO-B. Most of the compounds showed a potent and selective MAO-A inhibitory activity especially 4e and 9g derivatives.Figure optionsDownload as PowerPoint slide
Journal: European Journal of Medicinal Chemistry - Volume 93, 26 March 2015, Pages 308–320