Combretastatin-chalcone hybrids: synthesis and cytotoxicity.

Abstract

A series of all-trans-1-aryl-4-aryl-5-aryl-2,4-pentanediene-1-one (3), a hybridized form of chalcone and combretastatin, was synthesized and evaluated against a panel of cancer cell lines, including B16, murine melanoma; HCT116, colon cancer; A431, human epidermoid carcinoma; and human umbilical venous endothelial cells (HUVEC). Structure-activity relationships analysis of this series revealed that a 2,5-dihydroxyphenyl at position 1 of the 2,4-pentanediene-1-one was essential for cytotoxicity. all-trans-1-(2,5-Dihydroxyphenyl)-5-(4-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-2,4-pentanediene-1-one (3a) was the most potent compound from this series.

• Authors: Nguyen-Hai Nam, Ahn Byung-Zun
• Journal: Medicinal chemistry (Shariqah (United Arab Emirates)) (Med Chem) Vol. 3 Issue 4 Pg. 373-7 (Jul 2007) ISSN: 1573-4064 [Print] Netherlands
• PMID: 17627575 (Publication Type: Journal Article)

Chemical References

• Bibenzyls
• Stilbenes
• Chalcone
• combretastatin

Topics

• Bibenzyls (chemical synthesis, chemistry, toxicity)
• Cell Line
• Cell Survival (drug effects)
• Chalcone (chemical synthesis, chemistry, toxicity)
• Humans
• Molecular Structure
• Neoplasms (pathology)
• Stilbenes (chemical synthesis, chemistry, toxicity)
• Structure-Activity Relationship