Synthesis of tyrosinase inhibitory (4-oxo-4H-pyran-2-yl)acrylic acid ester derivatives

Soo Sung Kang; Hyoung Ja Kim; Changbae Jin; Yong Sup Lee

doi:10.1016/j.bmcl.2008.10.119

Synthesis of tyrosinase inhibitory (4-oxo-4H-pyran-2-yl)acrylic acid ester derivatives

Soo Sung Kang, Hyoung Ja Kim, Changbae Jin, Yong Sup Lee

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

55 Scopus citations

Abstract

Melanogenesis is a physiological process that results in the production of melanin pigment. However, excessive accumulations of epidermal pigmentation can cause various hyperpigmentary disorders such as, melasma and age spots. Kojic acid and hydroxylated cinnamic acid derivatives are known to inhibit tyrosinase, a key component of melanin biosynthesis. Pyronyl-acrylic acid esters 3a-i, which share structural features of kojic acid and hydroxylated cinnamic acid, were prepared and their abilities to inhibit tyrosinase and melanin production were evaluated. Of the esters synthesized, 3e and 3h, which derived from diethylene glycol moieties were found to inhibit melanin production by ca. 20% at 20 μg/ml, whereas kojic acid at 200 μg/ml inhibited melanin production by 15.8%.

Original language	English
Pages (from-to)	188-191
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	1
DOIs	https://doi.org/10.1016/j.bmcl.2008.10.119
State	Published - 1 Jan 2009

Bibliographical note

Funding Information:
This research was supported by the Seoul Research and Business Development Program (10524).

Keywords

Kojic acid
Melanin production
Pyronyl
Skin-whitening
Tyrosinase inhibitor

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10.1016/j.bmcl.2008.10.119

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title = "Synthesis of tyrosinase inhibitory (4-oxo-4H-pyran-2-yl)acrylic acid ester derivatives",

abstract = "Melanogenesis is a physiological process that results in the production of melanin pigment. However, excessive accumulations of epidermal pigmentation can cause various hyperpigmentary disorders such as, melasma and age spots. Kojic acid and hydroxylated cinnamic acid derivatives are known to inhibit tyrosinase, a key component of melanin biosynthesis. Pyronyl-acrylic acid esters 3a-i, which share structural features of kojic acid and hydroxylated cinnamic acid, were prepared and their abilities to inhibit tyrosinase and melanin production were evaluated. Of the esters synthesized, 3e and 3h, which derived from diethylene glycol moieties were found to inhibit melanin production by ca. 20% at 20 μg/ml, whereas kojic acid at 200 μg/ml inhibited melanin production by 15.8%.",

keywords = "Kojic acid, Melanin production, Pyronyl, Skin-whitening, Tyrosinase inhibitor",

author = "Kang, {Soo Sung} and Kim, {Hyoung Ja} and Changbae Jin and Lee, {Yong Sup}",

note = "Funding Information: This research was supported by the Seoul Research and Business Development Program (10524).",

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doi = "10.1016/j.bmcl.2008.10.119",

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T1 - Synthesis of tyrosinase inhibitory (4-oxo-4H-pyran-2-yl)acrylic acid ester derivatives

AU - Kang, Soo Sung

AU - Kim, Hyoung Ja

AU - Jin, Changbae

AU - Lee, Yong Sup

N1 - Funding Information: This research was supported by the Seoul Research and Business Development Program (10524).

PY - 2009/1/1

Y1 - 2009/1/1

N2 - Melanogenesis is a physiological process that results in the production of melanin pigment. However, excessive accumulations of epidermal pigmentation can cause various hyperpigmentary disorders such as, melasma and age spots. Kojic acid and hydroxylated cinnamic acid derivatives are known to inhibit tyrosinase, a key component of melanin biosynthesis. Pyronyl-acrylic acid esters 3a-i, which share structural features of kojic acid and hydroxylated cinnamic acid, were prepared and their abilities to inhibit tyrosinase and melanin production were evaluated. Of the esters synthesized, 3e and 3h, which derived from diethylene glycol moieties were found to inhibit melanin production by ca. 20% at 20 μg/ml, whereas kojic acid at 200 μg/ml inhibited melanin production by 15.8%.

AB - Melanogenesis is a physiological process that results in the production of melanin pigment. However, excessive accumulations of epidermal pigmentation can cause various hyperpigmentary disorders such as, melasma and age spots. Kojic acid and hydroxylated cinnamic acid derivatives are known to inhibit tyrosinase, a key component of melanin biosynthesis. Pyronyl-acrylic acid esters 3a-i, which share structural features of kojic acid and hydroxylated cinnamic acid, were prepared and their abilities to inhibit tyrosinase and melanin production were evaluated. Of the esters synthesized, 3e and 3h, which derived from diethylene glycol moieties were found to inhibit melanin production by ca. 20% at 20 μg/ml, whereas kojic acid at 200 μg/ml inhibited melanin production by 15.8%.

KW - Kojic acid

KW - Melanin production

KW - Pyronyl

KW - Skin-whitening

KW - Tyrosinase inhibitor

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SN - 0960-894X

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 1

ER -

Synthesis of tyrosinase inhibitory (4-oxo-4H-pyran-2-yl)acrylic acid ester derivatives

Abstract

Bibliographical note

Keywords

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