title: Synthesis and evaluation of 2(3H)-thiazole thiones as tyrosinase inhibitors.
abstract: A series of 2(3H)-thiazole thiones 3-5 was synthesized and evaluated for tyrosinase inhibition and DPPH radical scavenging activities. Among them, 3-methyl-4-phenyl-2(3H)-thiazole thione (4a) showed good tyrosinase inhibitory activity, even better than that of the well-known tyrosinase inhibitor, namely, kojic acid. From the structure-activity point of view, although it was found that the phenolic hydroxyl group in prototype 3-5 might contribute to the scavenging activity against DPPH radicals, there was no correlation between the potency of tyrosinase inhibition and the presence of the phenolic moiety. The in silico ADME-Tox screening revealed that the drug-likeness and drug-score values of the most potent compound 4a were significantly higher than those of kojic acid.
authors.affiliation: Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Mazandaran University of Medical Sciences, Sari, Iran. sd_emami@yahoo.com
authors.forename: Saeed
authors.initials: S
authors.lastname: Emami
authors.forename: Seyed Jalal
authors.initials: SJ
authors.lastname: Hosseinimehr
authors.forename: Kami
authors.initials: K
authors.lastname: Shahrbandi
authors.forename: Ahmad Ali
authors.initials: AA
authors.lastname: Enayati
authors.forename: Zahra
authors.initials: Z
authors.lastname: Esmaeeli
mesh_terms: D004353:Drug Evaluation, Preclinical / Q000379:methods; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D066298:In Vitro Techniques; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D011753:Pyrones / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013871:Thiones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D004791:Enzyme Inhibitors; D016166:Free Radical Scavengers; D011753:Pyrones; D013844:Thiazoles; D013871:Thiones; C011890:kojic acid; D014442:Monophenol Monooxygenase