Cross metathesis with hydroxamate and benzamide BOC-protected alkenes to access HDAC inhibitors and their biological evaluation highlighted intrinsic activity of BOC-protected dihydroxamates.

Vincent Zwick, Alessandra Nurisso, Claudia Simões-Pires, Samuel Bouchet, Nadine Martinet, Attila Lehotzky, Judit Ovadi, Muriel Cuendet, Christophe Blanquart, Philippe Bertrand

Bioorganic & medicinal chemistry letters 2016 Jan 1

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Conditions for the metathesis of alkenes in the convergent synthesis of HDAC inhibitors have been improved by continuous catalyst flow injection in the reaction media. Intermediate and target compounds obtained were tested for their ability to induce HDAC inhibition and tubulin acetylation, revealing the key role of the tert-butyloxycarbonyl (BOC) group for more HDAC6 selectivity. Molecular modelling added rationale for this BOC effect. Copyright © 2015 Elsevier Ltd. All rights reserved.

Citation

Vincent Zwick, Alessandra Nurisso, Claudia Simões-Pires, Samuel Bouchet, Nadine Martinet, Attila Lehotzky, Judit Ovadi, Muriel Cuendet, Christophe Blanquart, Philippe Bertrand. Cross metathesis with hydroxamate and benzamide BOC-protected alkenes to access HDAC inhibitors and their biological evaluation highlighted intrinsic activity of BOC-protected dihydroxamates. Bioorganic & medicinal chemistry letters. 2016 Jan 1;26(1):154-9