Synthesis and SAR of C12-C13-oxazoline derivatives of epothilone A

Pfeiffer, Bernhard; Hauenstein, Kurt; Merz, Philipp; Gertsch, Jürg; Altmann, Karl-Heinz (2009). Synthesis and SAR of C12-C13-oxazoline derivatives of epothilone A. Bioorganic and medicinal chemistry letters, 19(14), pp. 3760-3. New York, N.Y.: Pergamon 10.1016/j.bmcl.2009.04.112

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The SAR of a series of new epothilone A derivatives with a 2-substituted-1,3-oxazoline moiety trans-fused to the C12-C13 bond of the deoxy macrocycle have been investigated with regard to tubulin polymerization induction and cancer cell growth inhibition. Significant differences in antiproliferative activity were observed between different analogs, depending on the nature of the substituent at the 2-position of the oxazoline ring. The most potent compounds showed comparable activity with the natural product epothilone A. Modeling studies provide a preliminary rationale for the observed SAR.

Item Type:

Journal Article (Original Article)

Division/Institute:

04 Faculty of Medicine > Pre-clinic Human Medicine > Institute of Biochemistry and Molecular Medicine

UniBE Contributor:

Gertsch, Jürg

ISSN:

0960-894X

Publisher:

Pergamon

Language:

English

Submitter:

Factscience Import

Date Deposited:

04 Oct 2013 15:12

Last Modified:

04 May 2014 23:23

Publisher DOI:

10.1016/j.bmcl.2009.04.112

PubMed ID:

19433359

Web of Science ID:

000267762600013

URI:

https://boris.unibe.ch/id/eprint/31620 (FactScience: 196251)

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