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Design and synthesis of thiourea derivatives with sulfur-containing heterocyclic scaffolds as potential tyrosinase inhibitors.
Bioorg Med Chem. 2016 Apr 15; 24(8):1866-71.BM

Abstract

Tyrosinase is a key enzyme during the production of melanins in plants and animals. A class of novel N-aryl-N'-substituted phenylthiourea derivatives (3a-i, 6a-k) were designed, synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed some 4,5,6,7-tetrahydro-2-[[(phenylamino)thioxomethyl]amino]-benzo[b]thiophene-3-carboxylic acid derivatives (3a-i) exhibited moderate inhibitory potency on diphenolase activity of tyrosinase. When the scaffold of 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid was replaced with 2-(1,3,4-thiadiazol-2-yl)thio acetic acid, the inhibitory activity of compounds (6a-k) against tyrosinase was improved obviously; especially, the inhibitory activity of compound 6h (IC50=6.13 μM) is significantly higher than kojic acid (IC50=33.3 μM). Moreover, the analysis on inhibition mechanism revealed that compound 6h might plays the role as a noncompetitive inhibitor.

Authors+Show Affiliations

Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China.Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China.Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China.Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China.Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China. Electronic address: yqpeng@ecust.edu.cn.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26972919

Citation

Liu, Pingping, et al. "Design and Synthesis of Thiourea Derivatives With Sulfur-containing Heterocyclic Scaffolds as Potential Tyrosinase Inhibitors." Bioorganic & Medicinal Chemistry, vol. 24, no. 8, 2016, pp. 1866-71.
Liu P, Shu C, Liu L, et al. Design and synthesis of thiourea derivatives with sulfur-containing heterocyclic scaffolds as potential tyrosinase inhibitors. Bioorg Med Chem. 2016;24(8):1866-71.
Liu, P., Shu, C., Liu, L., Huang, Q., & Peng, Y. (2016). Design and synthesis of thiourea derivatives with sulfur-containing heterocyclic scaffolds as potential tyrosinase inhibitors. Bioorganic & Medicinal Chemistry, 24(8), 1866-71. https://doi.org/10.1016/j.bmc.2016.03.013
Liu P, et al. Design and Synthesis of Thiourea Derivatives With Sulfur-containing Heterocyclic Scaffolds as Potential Tyrosinase Inhibitors. Bioorg Med Chem. 2016 Apr 15;24(8):1866-71. PubMed PMID: 26972919.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Design and synthesis of thiourea derivatives with sulfur-containing heterocyclic scaffolds as potential tyrosinase inhibitors. AU - Liu,Pingping, AU - Shu,Chen, AU - Liu,Lujie, AU - Huang,Qingchun, AU - Peng,Yanqing, Y1 - 2016/03/05/ PY - 2016/01/22/received PY - 2016/03/01/revised PY - 2016/03/04/accepted PY - 2016/3/15/entrez PY - 2016/3/15/pubmed PY - 2016/12/21/medline KW - Inhibition KW - Thiadiazol KW - Thiophene KW - Thiourea derivatives KW - Tyrosinase SP - 1866 EP - 71 JF - Bioorganic & medicinal chemistry JO - Bioorg. Med. Chem. VL - 24 IS - 8 N2 - Tyrosinase is a key enzyme during the production of melanins in plants and animals. A class of novel N-aryl-N'-substituted phenylthiourea derivatives (3a-i, 6a-k) were designed, synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed some 4,5,6,7-tetrahydro-2-[[(phenylamino)thioxomethyl]amino]-benzo[b]thiophene-3-carboxylic acid derivatives (3a-i) exhibited moderate inhibitory potency on diphenolase activity of tyrosinase. When the scaffold of 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid was replaced with 2-(1,3,4-thiadiazol-2-yl)thio acetic acid, the inhibitory activity of compounds (6a-k) against tyrosinase was improved obviously; especially, the inhibitory activity of compound 6h (IC50=6.13 μM) is significantly higher than kojic acid (IC50=33.3 μM). Moreover, the analysis on inhibition mechanism revealed that compound 6h might plays the role as a noncompetitive inhibitor. SN - 1464-3391 UR - https://www.unboundmedicine.com/medline/citation/26972919/Design_and_synthesis_of_thiourea_derivatives_with_sulfur_containing_heterocyclic_scaffolds_as_potential_tyrosinase_inhibitors_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(16)30162-6 DB - PRIME DP - Unbound Medicine ER -