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Synthesis and Evaluation of 2(3 H )‐Thiazole Thiones as Tyrosinase Inhibitors
Author(s) -
Emami Saeed,
Hosseinimehr Seyed Jalal,
Shahrbandi Kami,
Enayati Ahmad Ali,
Esmaeeli Zahra
Publication year - 2012
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201200028
Subject(s) - thiazole , chemistry , tyrosinase , stereochemistry , combinatorial chemistry , chemical synthesis , organic chemistry , enzyme , biochemistry , in vitro
A series of 2(3 H )‐thiazole thiones 3 – 5 was synthesized and evaluated for tyrosinase inhibition and DPPH radical scavenging activities. Among them, 3‐methyl‐4‐phenyl‐2(3 H )‐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.