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 microg/ml, whereas kojic acid at 200 microg/ml inhibited melanin production by 15.8%.
authors.affiliation: Life Sciences Research Division, Korea Institute of Science and Technology, Cheongryang, Seoul, Republic of Korea.
authors.forename: Soo Sung
authors.initials: SS
authors.lastname: Kang
authors.forename: Hyoung Ja
authors.initials: HJ
authors.lastname: Kim
authors.forename: Changbae
authors.initials: C
authors.lastname: Jin
authors.forename: Yong Sup
authors.initials: YS
authors.lastname: Lee
mesh_terms: D000179:Acrylates / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002934:Cinnamates; D004952:Esters / Q000138:chemical synthesis* / Q000494:pharmacology; D008543:Melanins / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D011753:Pyrones / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000179:Acrylates; D002934:Cinnamates; D004952:Esters; D008543:Melanins; D011753:Pyrones; C029010:cinnamic acid; C011890:kojic acid; D014442:Monophenol Monooxygenase; C036658:acrylic acid