Issue 24, 2008
From the journal:

Organic & Biomolecular Chemistry

Design, synthesis and biological evaluation of bridged epothilone D analogues†

Qiao-Hong Chen,‡a   Thota Ganesh,‡ab   Peggy Brodie,a   Carla Slebodnick,a   Yi Jiang,c   Abhijit Banerjee,b   Susan Bane,c   James P. Snyderb  and  David G. I. Kingston*a  

* Corresponding authors

a Department of Chemistry, M/C 0212, Virginia Polytechnic Institute and State University, Blacksburg, Virginia, USA
E-mail: qchen06@vt.edu, dkingston@vt.edu
Fax: 1 540 231 3255
Tel: 1 540-231-6570

b Department of Chemistry, Emory University, Atlanta, GA, USA
E-mail: jsnyder@emory.edu, tganesh@emory.edu

c Department of Chemistry, State University of New York of Binghamton, Binghamton, NY, USA
E-mail: sbane@binghamton.edu

Abstract

Six epothilone D analogues with a bridge between the C4-methyl and the C12-methyl carbons were prepared in an attempt to constrain epothilone D to its proposed tubulin-binding conformation. Ring-closing metathesis (RCM) was employed as the key step to build the C4–C26 bridge. In antiproliferative assays in the human ovarian cancer (A2780) and prostate cancer (PC3) cell lines, and also in tubulin assembly assay, all these compounds proved to be less active than epothilone D.

Graphical abstract: Design, synthesis and biological evaluation of bridged epothilone D analogues

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Article information

DOI
https://doi.org/10.1039/B814823F
Article type
Paper
Submitted
26 Aug 2008
Accepted
26 Sep 2008
First published
06 Nov 2008

Org. Biomol. Chem., 2008,6, 4542-4552

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Design, synthesis and biological evaluation of bridged epothilone D analogues

Q. Chen, T. Ganesh, P. Brodie, C. Slebodnick, Y. Jiang, A. Banerjee, S. Bane, J. P. Snyder and D. G. I. Kingston, Org. Biomol. Chem., 2008, 6, 4542 DOI: 10.1039/B814823F

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