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Synthesis and biological evaluation of novel hydroxybenzaldehyde-based kojic acid analogues as inhibitors of mushroom tyrosinase.
Bioorg Med Chem Lett. 2017 02 01; 27(3):530-532.BM

Abstract

Two series of novel kojic acid analogues (4a-j) and (5a-d) were designed and synthesized, and their mushroom tyrosinase inhibitory activities was evaluated. The result indicated that all the synthesized derivatives exhibited excellent tyrosinase inhibitory properties having IC50 values in the range of 1.35±2.15-17.50±2.75μM, whereas standard inhibitor kojic acid have IC50 values 20.00±1.08μM. Specifically, 5-phenyl-3-[5-hydroxy-4-pyrone-2-yl-methylmercap-to]-4-(2,4-dihydroxyl-benzylamino)-1,2,4-triazole (4f) exhibited the most potent tyrosinase inhibitory activity with IC50 value of 1.35±2.15μM. The kinetic studies of the compound (4f) demonstrated that the inhibitory effects of the compound on the tyrosinase were belonging to competitive inhibitors. Meanwhile, the structure-activity relationship was discussed.

Authors+Show Affiliations

School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China; Key Laboratory of Theoretical Organic Chemistry and Function Molecule of Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201, China; Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, Xiangtan 411201, China. Electronic address: xwl99zsu@163.com.School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.

Pub Type(s)

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

Language

eng

PubMed ID

28011217

Citation

Xie, Wenlin, et al. "Synthesis and Biological Evaluation of Novel Hydroxybenzaldehyde-based Kojic Acid Analogues as Inhibitors of Mushroom Tyrosinase." Bioorganic & Medicinal Chemistry Letters, vol. 27, no. 3, 2017, pp. 530-532.
Xie W, Zhang H, He J, et al. Synthesis and biological evaluation of novel hydroxybenzaldehyde-based kojic acid analogues as inhibitors of mushroom tyrosinase. Bioorg Med Chem Lett. 2017;27(3):530-532.
Xie, W., Zhang, H., He, J., Zhang, J., Yu, Q., Luo, C., & Li, S. (2017). Synthesis and biological evaluation of novel hydroxybenzaldehyde-based kojic acid analogues as inhibitors of mushroom tyrosinase. Bioorganic & Medicinal Chemistry Letters, 27(3), 530-532. https://doi.org/10.1016/j.bmcl.2016.12.027
Xie W, et al. Synthesis and Biological Evaluation of Novel Hydroxybenzaldehyde-based Kojic Acid Analogues as Inhibitors of Mushroom Tyrosinase. Bioorg Med Chem Lett. 2017 02 1;27(3):530-532. PubMed PMID: 28011217.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and biological evaluation of novel hydroxybenzaldehyde-based kojic acid analogues as inhibitors of mushroom tyrosinase. AU - Xie,Wenlin, AU - Zhang,Huilin, AU - He,Jingjing, AU - Zhang,Jingai, AU - Yu,Qiuyan, AU - Luo,Chunxiang, AU - Li,Shangru, Y1 - 2016/12/09/ PY - 2016/08/09/received PY - 2016/11/17/revised PY - 2016/12/08/accepted PY - 2016/12/25/pubmed PY - 2017/6/28/medline PY - 2016/12/25/entrez KW - 1,2,4-Triazole KW - Benzaldehyde KW - Kojic acid KW - Tyrosinase inhibitors SP - 530 EP - 532 JF - Bioorganic & medicinal chemistry letters JO - Bioorg Med Chem Lett VL - 27 IS - 3 N2 - Two series of novel kojic acid analogues (4a-j) and (5a-d) were designed and synthesized, and their mushroom tyrosinase inhibitory activities was evaluated. The result indicated that all the synthesized derivatives exhibited excellent tyrosinase inhibitory properties having IC50 values in the range of 1.35±2.15-17.50±2.75μM, whereas standard inhibitor kojic acid have IC50 values 20.00±1.08μM. Specifically, 5-phenyl-3-[5-hydroxy-4-pyrone-2-yl-methylmercap-to]-4-(2,4-dihydroxyl-benzylamino)-1,2,4-triazole (4f) exhibited the most potent tyrosinase inhibitory activity with IC50 value of 1.35±2.15μM. The kinetic studies of the compound (4f) demonstrated that the inhibitory effects of the compound on the tyrosinase were belonging to competitive inhibitors. Meanwhile, the structure-activity relationship was discussed. SN - 1464-3405 UR - https://www.unboundmedicine.com/medline/citation/28011217/Synthesis_and_biological_evaluation_of_novel_hydroxybenzaldehyde_based_kojic_acid_analogues_as_inhibitors_of_mushroom_tyrosinase_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0960-894X(16)31294-X DB - PRIME DP - Unbound Medicine ER -