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Synthesis and Biological Evaluation of New Thiosemicarbazone Derivative Schiff Bases as Monoamine Oxidase Inhibitory Agents

1
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, 26470 Eskişehir, Turkey
2
Doping and Narcotic Compounds Analysis Laboratory, Faculty of Pharmacy, Anadolu University, 26470 Eskişehir, Turkey
3
Department of Pharmaceutical Toxicology, Faculty of Pharmacy, Anadolu University, 26470 Eskişehir, Turkey
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(1), 60; https://doi.org/10.3390/molecules23010060
Received: 15 November 2017 / Revised: 13 December 2017 / Accepted: 21 December 2017 / Published: 28 December 2017
(This article belongs to the Section Medicinal Chemistry)
Twenty-six novel thiosemicarbazone derivative B1B26 were synthesized via condensation reactions between the corresponding thiosemicarbazides and aldehydes. The chemical characterization of the compounds was carried out by infrared (IR), mass (MS), proton and carbon nuclear magnetic resonance (1H- and 13C-NMR) spectroscopic analyses. The compounds were investigated for their monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) inhibitory activity and most of them were more potent against MAO-A enzyme when compared with MAO-B enzyme. N-Cyclohexyl-2-[4-[(4-chlorophenyl)thio]benzylidene]hydrazine-1-carbothioamide (B24) was the most active compound against MAO-A. The enzyme kinetics study revealed that compound B24 has a reversible and competitive mode of binding. Interaction modes between compound B24 and MAO-A were clarified by docking studies. In addition, the favourable absorption, distribution, metabolism, and excretion (ADME) properties and non-toxic nature of compound B24 make this compound a promising MAO-A inhibitor. View Full-Text
Keywords: thiosemicarbazone; MAO-A; MAO-B; docking; MTT; enzyme kinetic study; ADME thiosemicarbazone; MAO-A; MAO-B; docking; MTT; enzyme kinetic study; ADME
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Çavuşoğlu, B.K.; Sağlık, B.N.; Osmaniye, D.; Levent, S.; Acar Çevik, U.; Karaduman, A.B.; Özkay, Y.; Kaplancıklı, Z.A. Synthesis and Biological Evaluation of New Thiosemicarbazone Derivative Schiff Bases as Monoamine Oxidase Inhibitory Agents. Molecules 2018, 23, 60.

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