Synthesis of Kojic Acid Derivatives Containing Phenolic Hydroxy Groups

Kadokawa, Jun Ichi; Nishikura, T.; Muraoka, Ryo; Tagaya, Hideyuki; Fukuoka, N.

doi:10.1081/scc-120017129

Cited by 26 publications

(13 citation statements)

References 3 publications

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“…However, the inhibitory activity of 1 is not sufficiently potent or unstable for storage for use in cosmetics. Accordingly, many semi-synthetic kojic acid derivatives were synthesized usually by the modification of C-7 hydroxyl group into ester [5] hydroxyphenyl ether [6], glycoside [7], and amide derivatives [8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Tyrosinase Inhibitory Kojic Acid Derivative

Lee¹,

Park

Kim

et al. 2006

Archiv der Pharmazie

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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 microM) than that of kojic acid (IC(50) = 30.61 microM). Compound 2 also exhibited potent melanin synthesis inhibitory activity (19.53% inhibition at 5 mug) 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 inhibitors.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Tyrosinase Inhibitory Kojic Acid Derivative

Lee¹,

Park

Kim

et al. 2006

Archiv der Pharmazie

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“…To increase its activity, many semi-synthetic kojic acid derivatives have been synthesized. Many of these compounds were formed by modifying the C-2 hydroxyl group to form esters, 6 ethers, 7 sulfides 8 and peptide 9 derivatives because C-5 enolic hydroxyl group is considered as a pharmacophore for tyrosinase inhibition. Recently, we synthesized a 2,4-dihydroxy benzoate ester of kojic acid containing an adamantane moiety (2) and evaluated its tyrosinase activity.…”

Section: Tyrosinasementioning

confidence: 99%

Studies on Tyrosinase Inhibitory and Antioxidant Activities of Benzoic Acid Derivatives Containing Kojic Acid Moiety

Rho¹,

Lee²,

Ahn³

et al. 2011

Bulletin of the Korean Chemical Society

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“…However, the inhibitory activity of kojic acid is not potent enough. To overcome this drawback, many semi-synthetic kojic acid derivatives were synthesized usually by the modification of C-2 hydroxyl group into ester, 5 hydroxyphenyl ether, 6 and glycoside. 7 Recently, two molecules of kojic acid were connected by ester 8 and ethylene.…”

Section: Tyrosinasementioning

confidence: 99%