title: Synthesis and preliminary in vitro biological evaluation of 5-chloro-2-(substituted phenyl)benzo[d]thiazole derivatives designed as novel antimelanogenesis agents.
abstract: We describe the design, synthesis, and biological activities of 5-chloro-2-(substituted phenyl)benzo[d]thiazole derivatives as novel tyrosinase inhibitors. Among them, 4-(5-chloro-2,3-dihydrobenzo[d]thiazol-2-yl)-2,6-dimethoxyphenol (MHY884) and 2-bromo-4-(5-chloro-benzo[d]thiazol-2-yl)phenol (MHY966) showed inhibitory activity higher than or similar to kojic acid, against mushroom tyrosinase. Therefore, we carried out kinetic studies on the two compounds with potent tyrosinase inhibitory effects. Kinetic analysis of tyrosinase inhibition revealed that all of these compounds are competitive inhibitors. MHY884 and MHY966 effectively inhibited tyrosinase activity and reduced melanin levels in B16 cells treated with α-melanocyte stimulating hormone (α-MSH). These data strongly suggest that the newly synthesized compounds MHY884 and MHY966 could suppress production of melanin via inhibition of tyrosinase activity.
authors.affiliation: Molecular Inflammation Research Center for Aging Intervention (MRCA), College of Pharmacy, Pusan National University, Busan 609-735, Republic of Korea.
authors.forename: Young Mi
authors.initials: YM
authors.lastname: Ha
authors.forename: Yohei
authors.initials: Y
authors.lastname: Uehara
authors.forename: Daeui
authors.initials: D
authors.lastname: Park
authors.forename: Hyoung Oh
authors.initials: HO
authors.lastname: Jeong
authors.forename: Ji Young
authors.initials: JY
authors.lastname: Park
authors.forename: Yun Jung
authors.initials: YJ
authors.lastname: Park
authors.forename: Ji Yeon
authors.initials: JY
authors.lastname: Lee
authors.forename: Hye Jin
authors.initials: HJ
authors.lastname: Lee
authors.forename: Yu Min
authors.initials: YM
authors.lastname: Song
authors.forename: Hyung Ryong
authors.initials: HR
authors.lastname: Moon
authors.forename: Hae Young
authors.initials: HY
authors.lastname: Chung
mesh_terms: D000363:Agaricales / Q000737:chemistry / Q000201:enzymology*; D000818:Animals; D045744:Cell Line, Tumor; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology*; D005656:Fungal Proteins / Q000037:antagonists & inhibitors* / Q000737:chemistry; D007700:Kinetics; D008543:Melanins / Q000037:antagonists & inhibitors / Q000096:biosynthesis*; D051379:Mice; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis / Q000494:pharmacology*
chemical_list: D004791:Enzyme Inhibitors; D005656:Fungal Proteins; D008543:Melanins; D013844:Thiazoles; D014442:Monophenol Monooxygenase