Synthesis, biological evaluation, and metabolic stability of chlorogenic acid derivatives possessing thiazole as potent inhibitors of α-MSH-stimulated melanogenesis. Issue 21 (1st November 2017)

• Record Type: Journal Article
• Authors: 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
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 27:Issue 21(2017)
• Page Start: 4854
• Page End: 4857
• Publication Date: 2017-11-01
• Subjects: Chlorogenic acid (CGA) -- Melanogenesis -- α-MSH -- Caffeamide -- Thiazole; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2017.09.044
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: A series of catechol and dioxolane analogs containing thiazole CGA derivatives have been synthesized and evaluated for their inhibitory activity against α-MSH. The inhibitory activity was improved by replacing an α, β-unsaturated carbonyl of previously reported caffeamides with thiazole motif. Surprisingly, compound7d, one of the derivatives of dioxolane analogs, displayed the most potent inhibitory activity with an IC50 of 0.90 μM. Further studies on metabolic stability and bioactivation potential were also accomplished.