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

Research output: Contribution to journalArticlepeer-review

49 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 languageEnglish
Pages (from-to)188-191
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number1
DOIs
StatePublished - 1 Jan 2009

Keywords

  • Kojic acid
  • Melanin production
  • Pyronyl
  • Skin-whitening
  • Tyrosinase inhibitor

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