Conformationally constrained analogues of diacylglycerol. 19. Synthesis and protein kinase C binding affinity of diacylglycerol lactones bearing an N-hydroxylamide side chain

J Med Chem. 2003 Jun 19;46(13):2790-3. doi: 10.1021/jm030082c.

Abstract

The structures of N-hydroxylamides 1a and 1b, previously reported by Lee et al. in J. Med. Chem. 2001, 44, 4309-4312 as strong protein kinase C (PK-C) ligands, were incorrect and correspond instead to esters 2a and 2b, respectively. Here, we report the synthesis and complete characterization of 1a and 1b together with the associated biological activity in terms of PK-C binding affinity.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • 4-Butyrolactone / chemical synthesis*
  • 4-Butyrolactone / chemistry
  • Diglycerides / chemical synthesis*
  • Diglycerides / chemistry
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Protein Binding
  • Protein Kinase C / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Diglycerides
  • Lactones
  • Ligands
  • N-hydroxy-N-((2-(hydroxymethyl)-4-(5-methyl-3-(2-methylpropyl)hexylidene)-5-oxo-(2-2,3-dihydrofuryl))methyl)-2,2-dimethylpropanamide
  • Protein Kinase C
  • 4-Butyrolactone