title: Conformationally constrained analogues of diacylglycerol. 19. Synthesis and protein kinase C binding affinity of diacylglycerol lactones bearing an N-hydroxylamide side chain.
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.
authors.affiliation: Laboratory of Medicinal Chemistry, Center for Cancer Research, National Cancer Institute at Frederick, National Institutes of Health, Frederick, Maryland 21702, USA.
authors.forename: Yongseok
authors.initials: Y
authors.lastname: Choi
authors.forename: Ji-Hye
authors.initials: JH
authors.lastname: Kang
authors.forename: Nancy E
authors.initials: NE
authors.lastname: Lewin
authors.forename: Peter M
authors.initials: PM
authors.lastname: Blumberg
authors.forename: Jeewoo
authors.initials: J
authors.lastname: Lee
authors.forename: Victor E
authors.initials: VE
authors.lastname: Marquez
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D004075:Diglycerides / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011485:Protein Binding; D011493:Protein Kinase C / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D004075:Diglycerides; D007783:Lactones; D008024:Ligands; C475521:N-hydroxy-N-((2-(hydroxymethyl)-4-(5-methyl-3-(2-methylpropyl)hexylidene)-5-oxo-(2-2,3-dihydrofuryl))methyl)-2,2-dimethylpropanamide; D011493:Protein Kinase C; D015107:4-Butyrolactone