en
Scientific article
English

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

Published inBioorganic & medicinal chemistry letters, vol. 26, no. 1, p. 154-159
Publication date2016
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.

Keywords
  • Alkenes/chemistry
  • Benzamides/chemistry
  • Dose-Response Relationship
  • Drug
  • Formic Acid Esters/chemistry
  • Histone Deacetylase Inhibitors/chemistry/pharmacology
  • Histone Deacetylases/metabolism
  • Humans
  • Hydroxamic Acids/chemistry
  • Models
  • Molecular
  • Molecular Structure
  • Structure-Activity Relationship
Citation (ISO format)
ZWICK, Vincent et al. Cross metathesis with hydroxamate and benzamide BOC-protected alkenes to access HDAC inhibitors and their biological evaluation highlighted intrinsic activity of BOC-protected dihydroxamates. In: Bioorganic & medicinal chemistry letters, 2016, vol. 26, n° 1, p. 154–159. doi: 10.1016/j.bmcl.2015.11.011
Main files (1)
Article (Published version)
accessLevelRestricted
Identifiers
ISSN of the journal0960-894X
421views
0downloads

Technical informations

Creation06/13/2017 9:35:00 PM
First validation06/13/2017 9:35:00 PM
Update time03/15/2023 1:47:33 AM
Status update03/15/2023 1:47:33 AM
Last indexation01/17/2024 12:11:18 AM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack