Issue 21, 2023
From the journal:

Organic & Biomolecular Chemistry

Total synthesis and biological evaluation of histone deacetylase inhibitor WF-3161†

Michael Kohr, ORCID logo a   Niklas Papenkordt, ORCID logo b   Manfred Jung ORCID logo b  and  Uli Kazmaier ORCID logo *a  

* Corresponding authors

a Organic Chemistry, Saarland University, D-66123 Saarbrücken, Germany
E-mail: u.kazmaier@mx.uni-saarland.de

b Institute of Pharmaceutical Sciences, University of Freiburg, Albertstr. 25, 79104 Freiburg, Germany

Abstract

A novel synthesis of the naturally occurring HDAC inhibitor WF-3161 is described. Key steps include the Matteson homologation to generate the stereogenic centres in the side chain, and Pd-catalysed C–H functionalisation to connect the side chain to the peptide backbone. WF-3161 was found to be highly selective for HDAC1, whereas no activity was observed towards HDAC6. High activity was also found against the cancer cell line HL-60.

Graphical abstract: Total synthesis and biological evaluation of histone deacetylase inhibitor WF-3161

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Article information

DOI
https://doi.org/10.1039/D3OB00641G
Article type
Communication
Submitted
24 Apr 2023
Accepted
10 May 2023
First published
16 May 2023
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2023,21, 4382-4387

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Total synthesis and biological evaluation of histone deacetylase inhibitor WF-3161

M. Kohr, N. Papenkordt, M. Jung and U. Kazmaier, Org. Biomol. Chem., 2023, 21, 4382 DOI: 10.1039/D3OB00641G

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