title: Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives.
abstract: A newly series of coumarylthiazole derivatives containing aryl urea/thiourea groups were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. The result showed that all the synthesized compounds exhibited inhibitory activity to both cholinesterases. Among them, 1-(4-(8-methoxy-2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-(4-chlorophenyl)thiourea (f8, IC50 = 4.58 μM) was found to be the most active compound against AChE, and 1-(4-fluorophenyl)-3-(4-(6-nitro-2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea (e31) exhibited the strongest inhibition against BuChE with IC50 value of 4.93 μM, which was 3.5-fold more potent than that of galantamine. The selectivity of f8 and e31 were 2.64 and 0.04, respectively. In addition, the cupric reducing antioxidant capacities (CUPRAC) and ABTS cation radical scavenging abilities of the synthesized compounds were investigated for antioxidant activity. Among them, f8, f4 and f6 (IC50=1.64, 1.82 and 2.69 μM, respectively) showed significantly better ABTS cation radical scavenging ability than standard quercetin (IC50 = 15.49 μM).
authors.affiliation: Bezmialem Vakif University, Faculty of Pharmacy, Deparment of Analytical and Medicinal Chemistry, 34093 Istanbul, Turkey.
authors.forename: Belma Zengin
authors.initials: BZ
authors.lastname: Kurt
authors.affiliation: Bezmialem Vakif University, Faculty of Pharmacy, Deparment of Analytical and Medicinal Chemistry, 34093 Istanbul, Turkey.
authors.forename: Isil
authors.initials: I
authors.lastname: Gazioglu
authors.affiliation: Sakarya University, Pamukova Vocational High School, 54900 Sakarya, Turkey. Electronic address: fsonmez@sakarya.edu.tr.
authors.forename: Fatih
authors.initials: F
authors.lastname: Sonmez
authors.affiliation: Sakarya University, Faculty of Arts and Science, Department of Chemistry, 54055 Sakarya, Turkey.
authors.forename: Mustafa
authors.initials: M
authors.lastname: Kucukislamoglu
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism; D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002091:Butyrylcholinesterase / Q000378:metabolism; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004593:Electrophorus; D006736:Horses; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014508:Urea / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D000975:Antioxidants; D002800:Cholinesterase Inhibitors; D003374:Coumarins; D013844:Thiazoles; D014508:Urea; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase
keywords: Acetylcholinesterase; Antioxidant; Butyrylcholinesterase; Coumarin; Thiazole