期刊
BIOORGANIC CHEMISTRY
卷 90, 期 -, 页码 -出版社
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.bioorg.2019.103063
关键词
Molecular docking; Kinetics; Quinolinyl acyl thioureas; Mushroom tyrosinase inhibitors; Free radical scavengers
The enzyme tyrosinase plays a vital role in melanin biosynthesis and enzymatic browning of vegetables and fruits. A series of novel quinolinyl thiourea analogues (11a-j) were synthesized by reaction of 3-aminoquinoline and corresponding isothiocyanates, in moderate to excellent yields with different substitutions and their inhibitory effect on mushroom tyrosinase and free radical scavenging activity were evaluated. The compound N-(quinolin-3-ylcarbamothioyl) hexanamide (11c) exhibited the maximum tyrosinase inhibitory effect (IC50 = 0.0070 +/- 0.0098 mu M) compared to other derivatives and the reference Kojic acid (IC50 = 16.8320 +/- 0.0621 mu M). The docking studies were carried out and the compound (11c) showed most negative estimated free energy of -7.2 kcal/mol in mushroom tyrosinase active site. The kinetic analysis revealed that the compound (11c) inhibits the enzyme tyrosinase non-competitively to form the complex of enzyme and inhibitor. The results revealed that 11c could be identified as putative lead compound for the design of efficient tyrosinase inhibitors.
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