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Letters in Drug Design & Discovery


ISSN (Print): 1570-1808
ISSN (Online): 1875-628X

A Stereospecific Route for the Preparation of Trans-Combretastatin Analogs: Synthesis and Cytotoxicity

Author(s): Hari Pati, Zarmeen Taherbhai, Lori Forrest, Martha Wicks, Suzanna Bailey, Andrew Staples, Michelle Stewart, William Pennington, Jeffrey Harris and Moses Lee

Volume 1 , Issue 3 , 2004

Page: [275 - 278] Pages: 4

DOI: 10.2174/1570180043398821

Price: $65


The stereospecific synthesis of nine trans-combretastatin analogs (5 - 13) is described. The trans geometry of these products was ascertained by the vinylenic proton NMR coupling constants of 15 - 16 Hz, and also by a single crystal x-ray structure of the tetramethoxy compound 6. Continuous 3-day exposure of murine B16 melanoma cells to the trans-combretastatin analogs 5 - 13 showed that two of the analogs (2 and 4) had good cytotoxicity. According to a MTT assay, the IC50 values for compounds 2 and 4 were 4.5 μM and 13.5 μM, respectively. Compounds that exhibited cytotoxic properties contain a 4,4-dimethoxy-transstilbene skeleton.

Keywords: combretastatin, tubulin, anticancer, chugaev reaction, cytotoxicity

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