RT Journal Article
SR Electronic
T1 Solution Conformations of Ethyl-1'-Methylbutylbarbituric Acids: Implications for Drug-Receptor Site Interactions
JF Molecular Pharmacology
JO Mol Pharmacol
FD American Society for Pharmacology and Experimental Therapeutics
SP 470
OP 477
VO 11
IS 4
A1 G. DOYLE DAVES, JR.
A1 RODNEY B. BELSHEE
A1 WILLIAM R. ANDERSON, JR.
A1 HALL DOWNES
YR 1975
UL http://molpharm.aspetjournals.org/content/11/4/470.abstract
AB Solution conformations of 5-ethyl-5-(1'-methylbutyl)-, 5-ethyl-5-(1',3'-dimethylbutyl)-, and 5-ethyl-5-(1',3',3'-trimethylbutyl)barbituric acids in a variety of solvents have been studied by nuclear magnetic resonance techniques. Implications of the results obtained in this study for discrimination between the enantiomers of 5-ethyl-5-(1',3'-dimethylbutyl)barbituric acid [R-(+), excitatory, and S-(-), depressant] at the excitatory receptor site are discussed. It is suggested that discrimination between the enantiomers is based primarily on a required binding orientation of the pyrimidinetrione ring and differing aliphatic side chain geometries resulting from a strong conformational preference of the isopropyl termini.