Synthesis, biological evaluation, and metabolic stability of chlorogenic acid derivatives possessing thiazole as potent inhibitors of alpha-MSH-stimulated melanogenesis

Jo, Hyeju; Zhou, Yuanyuan; Viji, Mayavan; Choi, Minho; Lim, Jae Young; Sim, Jaeuk; Rhee, Jeongtae; Kim, Youngsoo; Seo, Seung-Yong; Kim, Wun-Jae; Hong, Jin Tae; Lee, Heesoon; Lee, Kiho; Jung, Jae-Kyung

doi:10.1016/j.bmcl.2017.09.044

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Synthesis, biological evaluation, and metabolic stability of chlorogenic acid derivatives possessing thiazole as potent inhibitors of alpha-MSH-stimulated melanogenesis

Jo, Hyeju;
Zhou, Yuanyuan;
Viji, Mayavan;
Choi, Minho;
Lim, Jae Young;
... Lee, Kiho;
외 8명

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12

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13

초록

A series of catechol and dioxolane analogs containing thiazole CGA derivatives have been synthesized and evaluated for their inhibitory activity against alpha-MSH. The inhibitory activity was improved by replacing an alpha,beta-unsaturated carbonyl of previously reported caffeamides with thiazole motif. Surprisingly, compound 7d, one of the derivatives of dioxolane analogs, displayed the most potent inhibitory activity with an IC50 of 0.90 mu M. Further studies on metabolic stability and bioactivation potential were also accomplished. (C) 2017 Elsevier Ltd. All rights reserved.

키워드

Chlorogenic acid (CGA); Melanogenesis; alpha-MSH; Caffeamide; Thiazole; NF-KAPPA-B; IN-VITRO; DRUG DISCOVERY; CAFFEIC ACID; PARAMETERS; AGENTS; MODEL

제목: Synthesis, biological evaluation, and metabolic stability of chlorogenic acid derivatives possessing thiazole as potent inhibitors of alpha-MSH-stimulated melanogenesis

저자: Jo, Hyeju; Zhou, Yuanyuan; Viji, Mayavan; Choi, Minho; Lim, Jae Young; Sim, Jaeuk; Rhee, Jeongtae; Kim, Youngsoo; Seo, Seung-Yong; Kim, Wun-Jae; Hong, Jin Tae; Lee, Heesoon; Lee, Kiho; Jung, Jae-Kyung

DOI: 10.1016/j.bmcl.2017.09.044

발행일: 2017-11-01

유형: Article

저널명: Bioorganic & Medicinal Chemistry Letters

권: 27

호: 21

페이지: 4854 ~ 4857