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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Weir, Ron / Stohner, Jürgen

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IMPACT FACTOR 2016: 2.626
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1365-3075
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Volume 81, Issue 2 (Jan 2009)

Issues

Total synthesis of novel dictyostatin analogs and hybrids as microtubule-stabilizing anticancer agents

Ian Paterson / Nicola M. Gardner / Guy J. Naylor
Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/PAC-CON-08-09-17

Structural modification of the dictyostatin macrolide template through adaptation of our total synthesis has led to the identification of a number of potent analogs of this novel microtubule-stabilizing agent. A common synthetic strategy was exploited, employing a (Z)-selective Still-Gennari olefination between various advanced C11-C26 aldehyde and C4-C10 (or C1-C10) β-ketophosphonate intermediates. In vitro evaluation of the growth inhibitory activity of these analogs against both Taxol-sensitive and -resistant human cancer cell lines has provided a foundation for structure-activity relationship (SAR) studies to help define the pharmacophore region.

Keywords: anticancer; macrolides; natural products; stereocontrolled synthesis; tubulin

Conference

International Conference on Organic Synthesis (ICOS 17), International Conference on Organic Synthesis, ICOS, Organic Synthesis, 17th, Daejeon, Korea, 2008-06-22–2008-06-27

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About the article

Published Online: 2009-01-01

Published in Print: 2009-01-01


Citation Information: Pure and Applied Chemistry, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-08-09-17.

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