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Synthesis of Tyrosinase Inhibitory Kojic Acid Derivative
Author(s) -
Lee Yong Sup,
Park Jang Hyun,
Kim Min Hwan,
Seo Seon Hee,
Kim Hyoung Ja
Publication year - 2006
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.200500213
Subject(s) - kojic acid , tyrosinase , chemistry , phosphonate , pyrone , stereochemistry , linker , aldehyde , derivative (finance) , combinatorial chemistry , organic chemistry , enzyme , catalysis , computer science , financial economics , economics , operating system
Kojic acid derivative 2 was synthesized by joining two pyrone rings through an ethylene linkage by Horner‐Emmons reaction of phosphonate 6 with aldehyde 7 . The intermediates 6 and 7 were derived from kojic acid. The tyrosinase inhibitory activity of 2 was about 8 times more potent (IC 50 = 3.63 μM) than that of kojic acid (IC 50 = 30.61 μM). Compound 2 also exhibited potent melanin synthesis inhibitory activity (19.53% inhibition at 5 μg) indicating that the connection of two pyrone rings of kojic acid through a suitable linker can be an useful strategy for identification of potent tyrosinase inhibitiors.