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Synthesis and biological evaluation of hydroxylated 3-phenylcoumarins as antioxidants and antiproliferative agents.

Abstract
Based on the observed biological activities of coumarins and resveratrol, we synthesized fourteen hydroxylated 3-phenylcoumarins (stilbene-coumarin hybrids) including six novel ortho-hydroxy-methoxy substituted derivatives, 1-14, by Perkin reaction. We characterized these compounds concerning their antioxidant activity against 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced pBR322 DNA strand breakage, and their antiproliferative effects on human promyelocytic leukemia HL-60 and human lung adenocarcinoma epithelial A549 cells. Structure-activity relationship information suggests that the introduction of ortho-hydroxy-methoxy groups and ortho-dihydroxy groups on the aromatic A ring could efficiently improve antiproliferative activity. Interestingly, a new derivative, 6-methoxy-7-hydroxy-3-(4'-hydroxyphenyl)coumarin, 9, behaved as a poor antioxidant but appeared to be the most potent antiproliferative agent among the compounds examined, and this activity was mediated by deregulation in cell cycle and induction of apoptosis.
AuthorsJie Yang, Guo-Yun Liu, Fang Dai, Xiao-Yan Cao, Yan-Fei Kang, Li-Mei Hu, Jiang-Jiang Tang, Xiu-Zhuang Li, Yan Li, Xiao-Ling Jin, Bo Zhou
JournalBioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 21 Issue 21 Pg. 6420-5 (Nov 01 2011) ISSN: 1464-3405 [Electronic] England
PMID21920747 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
CopyrightCopyright © 2011 Elsevier Ltd. All rights reserved.
Chemical References
  • Antineoplastic Agents
  • Antioxidants
  • Coumarins
Topics
  • Adenocarcinoma (pathology)
  • Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
  • Antioxidants (chemical synthesis, chemistry, pharmacology)
  • Cell Line, Tumor
  • Coumarins (chemical synthesis, chemistry, pharmacology)
  • DNA Damage
  • Drug Evaluation, Preclinical
  • Humans
  • Lung Neoplasms (pathology)
  • Structure-Activity Relationship

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