Exploiting the Biginelli reaction: nitrogen-rich pyrimidine-based tercyclic alpha-helix mimetics
Publication Year 2016, Volume 72, Issue #9, Page 1151-1160
Journal Title
Publication Type
Journal Article
Several rationally designed pyrimidine-based scaffolds intended to mimic the spatial projection of the i, i+3, and i+7 residues of an alpha-helix and also possess improved aqueous solubility were prepared. A Biginelli-oxidation process was used to form the central pyrimidine ring of these scaffolds, which was subsequently manipulated to form pyrimidine-based tercyclic alpha-helix mimetics. A pyrimidine-based scaffold designed to mimic the alpha-helical BH3 domain of the pro-apoptotic Bak protein was also prepared as a putative inhibitor of the BcI-x(L)/Bak protein-protein interaction. The pyrimidine-based tercyclic alpha-helix mimetics, and the putative Bcl-x(L) inhibitor, were assessed using a luminescence competition assay, however, none displayed inhibitory activity against Bel-x(L) or Mcl-1. (C) 2016 Elsevier Ltd. All rights reserved.
WEHI Research Division(s)
Chemical Biology
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Creation Date: 2016-06-15 08:51:08
Last Modified: 2016-06-15 09:11:03
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