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Design and Synthesis of 2-(3-Benzo[b]thienyl)-6,7-methylenedioxyquinolin-4-one Analogues as Potent Antitumor Agents that Inhibit Tubulin Assembly

  1. Author:
    Chang, Y. H.
    Hsu, M. H.
    Wang, S. H.
    Huang, L. J.
    Qian, K.
    Morris-Natschke, S. L.
    Hamel, E.
    Kuo, S. C.
    Lee, K. H.

  2. Author Address

    Chang, Yu-Hsun, Hsu, Mei-Hua, Huang, Li-Jiau, Kuo, Sheng-Chu] China Med Univ, Grad Inst Pharmaceut Chem, Taichung, Taiwan. [Wang, Sheng-Hung] Acad Sinica, Inst Cellular & Organism Biol, Taipei 115, Taiwan. [Qian, Keduo, Morris-Natschke, Susan L.; Lee, Kuo-Hsiung] Univ N Carolina, Sch Pharm, UNC Eshelman, Nat Prod Res Labs, Chapel Hill, NC 27599 USA. [Hamel, Ernest] NCI, Toxicol & Pharmacol Branch, Dev Therapeut Program, Div Canc Treatment & Diag,NIH, Frederick, MD 21702 USA.
    1. Year: 2009
  2. Journal: Journal of Medicinal Chemistry
    1. 52
    2. 15
    3. Pages: 4883-4891
  4. Type of Article: Article
  1. Abstract:

    As part of our continuing investigation of azo-flavonoid derivatives as potential anticancer drug candidates, a series of 2-aryl-6,7-methylenedioxyquinolin-4-one analogues was designed and synthesized. The design combined structural features of 2-(2-fluorophenyl)-6,7-methylenedioxyquinolin-4-one (CHM-1), a previously discovered compound with potent in vivo antitumor activity, and 2-arylquinolin-4-ones, identified by CoMFA models, The newly synthesized analogues were evaluated for cytotoxicity against seven human cancer cell lines, and structure-activity relationship (SAR) correlations were established. Analogues 1, 37, and 39 showed potent cytotoxicity against different cancer cell lines. Compound I demonstrated selective cytotoxicity against Hep 3B (hepatoma) cells. Compound 37 was cytotoxic against HL-60 (leukemia), HCT-116 (colon cancer), Hep 3B (hepatoma), and SK-MEL-5 (melanoma) cells. Compound 39 exhibited broad cytotoxicity against all seven cancer cell lines, with IC50 values between 0.07and 0.19 mu M. Results from mechanism of action studies revealed that these new quinolone derivatives function as antitubulin agents.

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  2. DOI: 10.1021/jm900456w
  3. PMID: 19719238

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