title: Rational design and synthesis of 4-o-substituted phenylmethylenethiosemicarbazones as novel tyrosinase inhibitors.
abstract: In continuing our program aimed to search for tyrosinase inhibitors, a series of novel 4-O-substituted phenylmethylenethiosemicarbazones were rational designed, synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were also evaluated. A fair number of compounds were found to have significant tyrosinase inhibitiory activity. Particularly, the IC(50) values of compounds 3a-g, 3j and 3s were of the same magnitude as tropolone, one of the best tyrosinase inhibitors known so far. Furthermore, the structure-activity relationships of these compounds were also investigated. All these data suggested that these molecules might be utilized for the development of new candidate for the treatment of dermatological disorders, and further development of such compounds may be of interest.
authors.affiliation: School of Chemistry and Chemical Engineering, Sun Yat-sen University, 135 Xin Gang West Road, Guangzhou 510275, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Yi
authors.forename: Rihui
authors.initials: R
authors.lastname: Cao
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Chen
authors.forename: Liang
authors.initials: L
authors.lastname: Yu
authors.forename: Huan
authors.initials: H
authors.lastname: Wen
authors.forename: Qin
authors.initials: Q
authors.lastname: Yan
authors.forename: Lin
authors.initials: L
authors.lastname: Ma
authors.forename: Huacan
authors.initials: H
authors.lastname: Song
mesh_terms: D000363:Agaricales / Q000187:drug effects / Q000201:enzymology; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D021281:Quantitative Structure-Activity Relationship; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D004791:Enzyme Inhibitors; D013882:Thiosemicarbazones; D014442:Monophenol Monooxygenase