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

Authors
  • Jo, Hyeju1
  • Zhou, Yuanyuan2
  • Viji, Mayavan1
  • Choi, Minho1
  • Lim, Jae Young1
  • Sim, Jaeuk1
  • Rhee, Jeongtae1
  • Kim, Youngsoo1
  • Seo, Seung-Yong3
  • Kim, Wun-Jae4
  • Hong, Jin Tae1
  • Lee, Heesoon1
  • Lee, Kiho5
  • Jung, Jae-Kyung6
  • 1 College of Pharmacy and Medicinal Research Center (MRC), Chungbuk National University, Cheongju 28160, Republic of Korea. , (North Korea)
  • 2 College of Pharmacy, Korea University, Sejong 30019, Republic of Korea. , (North Korea)
  • 3 College of Pharmacy and Gachon Institute of Pharmaceutical Sciences, Gachon University, Incheon 21936, Republic of Korea. , (North Korea)
  • 4 College of Medicines, Chungbuk National University, Cheongju 28644, Republic of Korea. , (North Korea)
  • 5 College of Pharmacy, Korea University, Sejong 30019, Republic of Korea. Electronic address: [email protected] , (North Korea)
  • 6 College of Pharmacy and Medicinal Research Center (MRC), Chungbuk National University, Cheongju 28160, Republic of Korea. Electronic address: [email protected] , (North Korea)
Type
Published Article
Journal
Bioorganic & medicinal chemistry letters
Publication Date
Nov 01, 2017
Volume
27
Issue
21
Pages
4854–4857
Identifiers
DOI: 10.1016/j.bmcl.2017.09.044
PMID: 28964634
Source
Medline
Keywords
License
Unknown

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, compound 7d, one of the derivatives of dioxolane analogs, displayed the most potent inhibitory activity with an IC50 of 0.90μM. Further studies on metabolic stability and bioactivation potential were also accomplished.

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