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Open AccessArticle

Design and Synthesis of New Benzothiazole Compounds as Selective hMAO-B Inhibitors

1
Department of Pharmaceutical Toxicology, Faculty of Pharmacy, Anadolu Universty, 26470, Eskişehir, Turkey
2
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu Universty, 26470, Eskişehir, Turkey
3
Doping and Narcotic Compounds Analysis Laboratory, Faculty of Pharmacy, Anadolu Universty, 26470, Eskişehir, Turkey
*
Author to whom correspondence should be addressed.
Molecules 2017, 22(12), 2187; https://doi.org/10.3390/molecules22122187
Received: 15 November 2017 / Revised: 1 December 2017 / Accepted: 8 December 2017 / Published: 9 December 2017
(This article belongs to the Section Bioorganic Chemistry)
In the current work a new class of novel benzothiazole-hydrazone derivatives was designed and synthesized as hMAO-B inhibitors. Structures of the obtained compounds (3a3j) were characterized by IR, 1H-NMR, 13C-NMR, and HRMS spectroscopic methods. The inhibitory activity of compounds (3a3j) against hMAO-A and hMAO-B enzymes was evaluated by using an in vitro fluorometric method. According to activity results, some of the synthesized compounds displayed selective and significant hMAO-B enzyme inhibitor activity. Compound 3e was the most active derivative in the series with an IC50 value of 0.060 µM. Furthermore, cytotoxicity of compound 3e was investigated and found to be non-cytotoxic. Absorption, distribution, metabolism, and excretion (ADME) and blood-brain barrier (BBB) permeability predictions were performed for all compounds. It was determined that these compounds may have a good pharmacokinetic profiles. Bınding modes between the most active compound 3e and the hMAO-B enzyme were analyzed by docking studies. It was observed that there is a strong interaction between compound 3e and enzyme active site. View Full-Text
Keywords: benzothiazole; hydrazone; MAO enzyme inhibition; docking study; cytotoxicity benzothiazole; hydrazone; MAO enzyme inhibition; docking study; cytotoxicity
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Ilgın, S.; Osmaniye, D.; Levent, S.; Sağlık, B.N.; Acar Çevik, U.; Çavuşoğlu, B.K.; Özkay, Y.; Kaplancıklı, Z.A. Design and Synthesis of New Benzothiazole Compounds as Selective hMAO-B Inhibitors. Molecules 2017, 22, 2187.

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