Synthesis of New Anti-melanogenic Compounds Containing Two Molecules of Kojic Acid

Rho, Ho‐Sik; Baek, Heung-Soo; Ahn, Soo-Mi; Kim, Duck-Hee; Chang, Ih-Seop

doi:10.5012/bkcs.2008.29.8.1569

Bulletin of the Korean Chemical Society

2008

DOI: 10.5012/bkcs.2008.29.8.1569

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Synthesis of New Anti-melanogenic Compounds Containing Two Molecules of Kojic Acid

Ho‐Sik Rho¹,

Heung-Soo Baek²,

Soo-Mi Ahn³

et al.

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Cited by 30 publications

(2 citation statements)

References 9 publications

(5 reference statements)

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“…In addition, a diester containing a succinoyl moiety coupled with two kojic acid units gave a better than 2-fold increase in inhibitory activity than kojic acid. 17 Based on the improvements in tyrosinase inhibitory activities upon structural modification of carvacrol, thymol and kojic acid, it was envisioned that alkyl 4oxobutanoate derivatives of carvacrol and thymol would give enhancement in activity relative to the parent phenols.…”

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“…Kojic acid (IC 50 = 21.8 μM), was used as a positive control. The compounds showed moderate inhibitory activity, with IC 50 values ranging from 122.8 to 244.1 μM for the carvacrol series (9-12) and 102.3-212.3 μM for the thymol series (15)(16)(17)(18)(19). Despite the anomalous percent inhibition of the carvacrol allyl 4-oxobutanoate (10), it showed the highest inhibitory activity among the carvacrol derivatives (IC 50 = 128.8 μM).…”

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Synthesis and tyrosinase inhibitory activities of 4-oxobutanoate derivatives of carvacrol and thymol

Brotzman

Graybill

et al. 2019

Bioorganic & Medicinal Chemistry Letters

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Carvacrol (1) and thymol (2) were converted to their alkyl 4-oxobutanoate derivatives (7-20) in three steps, and evaluated for tyrosinase inhibitory activity. The compounds showed structuredependent activity, with all alkyl 4-oxobutanoates, except 7 and 20, showing better inhibitory activity than the precursor 4-oxobutanoic acids (5 and 6). In general, thymol derivatives exhibited a higher percent inhibitory activity than carvacrol derivatives at 500 μM. Derivatives containing three and four carbon alkyl groups gave the strongest activity (carvacrol derivatives 9-12, IC 50 = 128.8-244.1 μM; thymol derivatives 16-19, IC 50 = 102.3-191.4 μM).

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confidence: 99%

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confidence: 99%

Synthesis and tyrosinase inhibitory activities of 4-oxobutanoate derivatives of carvacrol and thymol

Brotzman

Graybill

et al. 2019

Bioorganic & Medicinal Chemistry Letters

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Evaluation of Kojyl Benzoate Derivatives as Potential Depigmenting Agents in Mouse B16/F1 Melanoma Cells

Choi

Kwon

Rho

et al. 2016

Bulletin Korean Chem Soc

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Organocatalytic Asymmetric Double Addition of Kojic Acids to 2‐Nitroallylic Carbonates

et al. 2022

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2-Nitroallylic carbonates were first applied as promising biselectrophilic C3 synthons for bifunctional squaramide catalyzed asymmetric domino reaction with kojic acid derivatives to afford so far inaccessible nitro compounds bearing two hydroxypyranone units. The reaction products undergo noncatalytic epimerization at the carbon atom next to the nitro group. Plausible mechanism of the epimerization based on reversible formation of intermediate aci-nitro compound is proposed. The double addition products were transformed to configurationally stable acetates and to chiral nitro glutarates, promising precursors to chiral amino glutaric acid derivatives.

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Synthesis of New Anti-melanogenic Compounds Containing Two Molecules of Kojic Acid

Cited by 30 publications

References 9 publications

Synthesis and tyrosinase inhibitory activities of 4-oxobutanoate derivatives of carvacrol and thymol

Synthesis and tyrosinase inhibitory activities of 4-oxobutanoate derivatives of carvacrol and thymol

Evaluation of Kojyl Benzoate Derivatives as Potential Depigmenting Agents in Mouse B16/F1 Melanoma Cells

Organocatalytic Asymmetric Double Addition of Kojic Acids to 2‐Nitroallylic Carbonates

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