Cross metathesis with hydroxamate and benzamide BOC-protected alkenes to access HDAC inhibitors and their biological evaluation highlighted intrinsic activity of BOC-protected dihydroxamates. Issue 1 (1st January 2016)

• Record Type: Journal Article
• Authors: Zwick, Vincent; Nurisso, Alessandra; Simões-Pires, Claudia; Bouchet, Samuel; Martinet, Nadine; Lehotzky, Attila; Ovadi, Judit; Cuendet, Muriel; Blanquart, Christophe; Bertrand, Philippe
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 26:Issue 1(2016)
• Page Start: 154
• Page End: 159
• Publication Date: 2016-01-01
• Subjects: Metathesis -- Histone deacetylases -- Cancer -- Tubulin; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2015.11.011
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: 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.