title: Synthesis of some novel 2-substituted benzothiazole derivatives containing benzylamine moiety as monoamine oxidase inhibitory agents.
abstract: In the present work, 12 new 2-(5-substituted-benzothiazol-2-ylsulfanyl)-N-(substitutedbenzyl)-N-(4-substitutedphenyl) acetamide derivatives (4a-l) was designed and synthesized. The structures of the synthesized compounds were clarified using Fourier transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance ((1)H-NMR), carbon-13 nuclear magnetic resonance ((13)C-NMR) and high-resolution mass spectrometry (HRMS) spectral data. Purity of synthesized compounds was checked by high-performance liquid chromatography (HPLC) analyses and purity ratio was found between 96.5-99.9%. The inhibitory activity of the compounds against MAO-A and MAO-B enzymes was evaluated by using in vitro flurometric method in which kynuramine was used as a substrate. Most of the compounds exhibited more selective inhibitory activity towards monoamine oxidase B (MAO-B) than monoamine oxidase A (MAO-A). Compound 4h was determined as the most potent compound against both enzyme types. The MAO-B enzyme kinetic of the compound 4h was studied and nature of MAO-B inhibition, caused by this compound, was investigated. The graphical analysis of steady-state inhibition data indicated that compound 4h is a mixed type inhibitor. Theoretical calculation of absorption, distribution, metabolism, excretion (ADME) properties for the synthesized compounds was also carried out and observed data supported the potential of compound 4h.
authors.affiliation: a Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Anadolu University , Eskişehir , Turkey and.
authors.forename: Betül
authors.initials: B
authors.lastname: Kaya
authors.affiliation: a Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Anadolu University , Eskişehir , Turkey and.|b Doping and Narcotic Compounds Analysis Laboratory, Faculty of Pharmacy, Anadolu University , Eskişehir , Turkey.
authors.forename: Begüm Nurpelin
authors.initials: BN
authors.lastname: Sağlık
authors.affiliation: a Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Anadolu University , Eskişehir , Turkey and.|b Doping and Narcotic Compounds Analysis Laboratory, Faculty of Pharmacy, Anadolu University , Eskişehir , Turkey.
authors.forename: Serkan
authors.initials: S
authors.lastname: Levent
authors.affiliation: a Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Anadolu University , Eskişehir , Turkey and.|b Doping and Narcotic Compounds Analysis Laboratory, Faculty of Pharmacy, Anadolu University , Eskişehir , Turkey.
authors.forename: Yusuf
authors.initials: Y
authors.lastname: Özkay
authors.affiliation: a Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Anadolu University , Eskişehir , Turkey and.
authors.forename: Zafer Asım
authors.initials: ZA
authors.lastname: Kaplancıklı
mesh_terms: D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001596:Benzylamines / Q000737:chemistry*; D008996:Monoamine Oxidase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013057:Spectrum Analysis
chemical_list: D052160:Benzothiazoles; D001596:Benzylamines; D008996:Monoamine Oxidase Inhibitors
keywords: Benzothiazole; MAO-A; MAO-B; kynuramine