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

Yongseok Choi; Ji-Hye Kang; Nancy E Lewin; Peter M Blumberg; Jeewoo Lee; Victor E Marquez

doi:10.1021/jm030082c

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.

Authors

Yongseok Choi¹, Ji-Hye Kang, Nancy E Lewin, Peter M Blumberg, Jeewoo Lee, Victor E Marquez

Affiliation

¹ Laboratory of Medicinal Chemistry, Center for Cancer Research, National Cancer Institute at Frederick, National Institutes of Health, Frederick, Maryland 21702, USA.

PMID: 12801241
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