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A direct alkylation route to branched derivatives of suberoylanilide hydroxamic acid (SAHA), a potent non-selective inhibitor of histone deacetylases

Dines, JA; Marson, CM; (2016) A direct alkylation route to branched derivatives of suberoylanilide hydroxamic acid (SAHA), a potent non-selective inhibitor of histone deacetylases. Tetrahedron , 72 (52) pp. 8584-8592. 10.1016/j.tet.2016.11.039. Green open access

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Abstract

Alkylation of malonamic esters provides a direct approach to derivatives of suberoylanilide hydroxamic acid (SAHA) that are branched at the amide carbon atom, a location pivotal for enhancing biological and therapeutic activity. Alkylations use NaH in THF followed by addition of the ester of 6-bromohexanoic acid; no protection of the amidic NH group is necessary. By this means, carboxylic acid, ester, amide, hydroxymethyl and 2-benzimidazolyl branching units have been appended to the SAHA backbone. Routes to vary one of the branching units at a time have been developed.

Type: Article
Title: A direct alkylation route to branched derivatives of suberoylanilide hydroxamic acid (SAHA), a potent non-selective inhibitor of histone deacetylases
Open access status: An open access version is available from UCL Discovery
DOI: 10.1016/j.tet.2016.11.039
Publisher version: http://dx.doi.org/10.1016/j.tet.2016.11.039
Language: English
Additional information: © 2016 Elsevier Ltd. All rights reserved. This manuscript version is made available under a Creative Commons Attribution Non-commercial Non-derivative 4.0 International license (CC BY-NC-ND 4.0). This license allows you to share, copy, distribute and transmit the work for personal and non-commercial use providing author and publisher attribution is clearly stated. Further details about CC BY licenses are available at https://creativecommons.org/licenses/. Access may be initially restricted by the publisher.
Keywords: Malonamic esters; Alkylation; Trifunctional compounds; Suberoylanilide hydroxamic acid; Histone deacetylase inhibitors
UCL classification: UCL
UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1533021
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