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1,2,3-Triazole-based kojic acid analogs as potent tyrosinase inhibitors: Design, synthesis and biological evaluation.

Abstract：

:A series of kojic acid-derived compounds 6a-p bearing aryloxymethyl-1H-1,2,3-triazol-1-yl moiety were designed by modifying primary alcoholic group of kojic acid as tyrosinase inhibitors. The target compounds 6a-p were synthesized via click reaction. All compounds showed very potent anti-tyrosinase activity (IC50s = 0.06-6.80 µM), being superior to reference drug, kojic acid. In particular, the naphthyloxy analogs 6o and 6p were found to be 31-155 times more potent than kojic acid. The metal-binding study of selected compound 6o revealed that the prototype compound possesses metal-chelating ability, particularly with Cu2+ ions. The promising compounds 6o and 6p had acceptable safety profile as demonstrated by cytotoxicity assay against melanoma (B16) cell line and Human Foreskin Fibroblast (HFF) cells.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Ashooriha M,Khoshneviszadeh M,Khoshneviszadeh M,Moradi SE,Rafiei A,Kardan M,Emami S

doi

10.1016/j.bioorg.2018.10.069

subject

Has Abstract

pub_date

2019-02-01 00:00:00

pages

414-422

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(18)30861-7

journal_volume

82

pub_type

杂志文章

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