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Int. J. Mol. Sci. 2017, 18(3), 648;

Synthesis and Biological Evaluation of 7-Deoxy-Epothilone Analogues

Department of Chemistry and Biochemistry, the Harper Cancer Research Institute, and the Warren Family Research Center for Drug Discovery & Development, University of Notre Dame, Notre Dame, IN 46556, USA
Eunice Kennedy Shriver National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, MD 20892, USA
Author to whom correspondence should be addressed.
Academic Editors: Susan L. Mooberry and John H. Miller
Received: 3 January 2017 / Revised: 6 February 2017 / Accepted: 22 February 2017 / Published: 17 March 2017
(This article belongs to the Special Issue Microtubule-Targeting Agents)
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The synthesis of two deoxygenated analogues of potent epothilones is reported in an effort to analyze the relative importance of molecular conformation and ligand–target interactions to biological activity. 7-deoxy-epothilone D and 7-deoxy-(S)-14-methoxy-epothilone D were prepared through total synthesis and shown to maintain the conformational preferences of their biologically active parent congeners through computer modeling and nuclear magnetic resonance (NMR) studies. The significant decrease in observed potency for each compound suggests that a hydrogen bond between the C7-hydroxyl group and the tubulin binding site plays a critical role in the energetics of binding in the epothilone class of polyketides. View Full-Text
Keywords: epothilone; conformation; binding site; cancer epothilone; conformation; binding site; cancer

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Woods, L.M.; Arico, J.W.; Frein, J.D.; Sackett, D.L.; Taylor, R.E. Synthesis and Biological Evaluation of 7-Deoxy-Epothilone Analogues. Int. J. Mol. Sci. 2017, 18, 648.

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