Abstract
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
Letters in Drug Design & Discovery
Title: A Stereospecific Route for the Preparation of Trans-Combretastatin Analogs: Synthesis and Cytotoxicity
Volume: 1 Issue: 3
Author(s): Hari Pati, Zarmeen Taherbhai, Lori Forrest, Martha Wicks, Suzanna Bailey, Andrew Staples, Michelle Stewart, William Pennington, Jeffrey Harris and Moses Lee
Affiliation:
Keywords: combretastatin, tubulin, anticancer, chugaev reaction, cytotoxicity
Abstract: 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.
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Pati Hari, Taherbhai Zarmeen, Forrest Lori, Wicks Martha, Bailey Suzanna, Staples Andrew, Stewart Michelle, Pennington William, Harris Jeffrey and Lee Moses, A Stereospecific Route for the Preparation of Trans-Combretastatin Analogs: Synthesis and Cytotoxicity, Letters in Drug Design & Discovery 2004; 1 (3) . https://dx.doi.org/10.2174/1570180043398821
DOI https://dx.doi.org/10.2174/1570180043398821 |
Print ISSN 1570-1808 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-628X |
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