Combretastatin-chalcone hybrids: synthesis and cytotoxicity.
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.
Nam
Nguyen-Hai
NH
Department of Pharmaceutical Chemistry, Hanoi University of Pharmacy, 13-15 Le Thanh Tong, Hanoi, Vietnam. nhnam@etal.uri.edu
Byung-Zun
Ahn
A
D001632:Bibenzyls / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D002599:Chalcone / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D006801:Humans; D015394:Molecular Structure; D009369:Neoplasms / Q000473:pathology; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D013329:Structure-Activity Relationship
D001632:Bibenzyls; D013267:Stilbenes; D002599:Chalcone; C040105:combretastatin