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

Hari Pati; Zarmeen Taherbhai; Lori Forrest; Martha Wicks; Suzanna Bailey; Andrew Staples; Michelle Stewart; William Pennington; Jeffrey Harris; Moses Lee

doi:10.2174/1570180043398821

ISSN: 1570-1808
E-ISSN: 1875-628X

A Stereospecific Route for the Preparation of Trans-Combretastatin Analogs: Synthesis and Cytotoxicity
Authors: Hari Pati¹, Zarmeen Taherbhai², Lori Forrest³, Martha Wicks⁴, Suzanna Bailey⁵, Andrew Staples⁶, Michelle Stewart⁷, William Pennington⁸, Jeffrey Harris⁹ and Moses Lee¹⁰
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¹ Department of Chemistry,Furman University, 3300 Poinsett Highway, Greenville, SC 29613, USA ² Department of Chemistry,Furman University, 3300 Poinsett Highway, Greenville, SC 29613, USA ³ Department of Chemistry,Furman University, 3300 Poinsett Highway, Greenville, SC 29613, USA ⁴ Department of Chemistry,Furman University, 3300 Poinsett Highway, Greenville, SC 29613, USA ⁵ Department of Chemistry,Furman University, 3300 Poinsett Highway, Greenville, SC 29613, USA ⁶ Department of Chemistry,Furman University, 3300 Poinsett Highway, Greenville, SC 29613, USA ⁷ Department of Chemistry,Furman University, 3300 Poinsett Highway, Greenville, SC 29613, USA ⁸ Department of Chemistry,Furman University, 3300 Poinsett Highway, Greenville, SC 29613, USA ⁹ Department of Chemistry,Furman University, 3300 Poinsett Highway, Greenville, SC 29613, USA ¹⁰ Department of Chemistry,Furman University, 3300 Poinsett Highway, Greenville, SC 29613, USA
Source: Letters in Drug Design & Discovery, Volume 1, Issue 3, Jul 2004, p. 275 - 278
DOI: https://doi.org/10.2174/1570180043398821
- Available online: 01 Jul 2004

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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2004-07-01

2025-09-29

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Article Type: Review Article

Keyword(s): anticancer; chugaev reaction; combretastatin; cytotoxicity; tubulin

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

Abstract

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