CONFORMATIONALLY CONSTRAINED ANALOGS OF DIACYLGLYCEROL .5. -DIDEOXY-3-O-TETRADECANOYL-D-GALACTONO-1,4-LACTONE - A SUPERIOR HOMOLOG OF 3-O-TETRADECANOYL-2-DEOXY-L-RIBONOLACTONE WITH PK-C BINDING-AFFINITY

Authors
SHARMA R MARQUEZ VE MILNE GWA LEWIN NE BLUMBERG PM
Citation
R. Sharma et al., CONFORMATIONALLY CONSTRAINED ANALOGS OF DIACYLGLYCEROL .5. -DIDEOXY-3-O-TETRADECANOYL-D-GALACTONO-1,4-LACTONE - A SUPERIOR HOMOLOG OF 3-O-TETRADECANOYL-2-DEOXY-L-RIBONOLACTONE WITH PK-C BINDING-AFFINITY, Bioorganic & medicinal chemistry letters, 3(10), 1993, pp. 1993-1998
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
10
Year of publication
1993
Pages
1993 - 1998
Database
ISI
SICI code
0960-894X(1993)3:10<1993:CCAOD.>2.0.ZU;2-5
Abstract
A computer-generated molecular superposition of the key pharmacophores in 3-O-tetradecanoyl-2-deoxy-L-ribonolactone (1) and phorbol-12-myris tate-13-acetate (PMA) indicated that the corresponding one carbon homo logue, -dideoxy-3-O-tetradecanoyl-D-galactono-1,4-lactone (2) would ha ve an improved fit to PMA. Compound 2 was synthesized, and, consistent with the model's prediction, demonstrated superior binding affinity f or PK-C relative to 1.