Ethyl 5-isopropoxy-4-methyl-beta-carboline-3-carboxylate: structural determinants of benzodiazepine-receptor antagonism.
Molecules of the title compound, C18H20N2O3, are linked into ribbons by N-H...O and N-H...N hydrogen bonds. Stereochemical comparison with Ro 15-1788 (viz. ethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate) has identified three electronegative N and O atoms in the molecule as features likely to be responsible for its activity as a benzodiazepine-receptor antagonist.
Camerman
Arthur
A
Ardono Research, 341 101st Avenue SE, Bellevue, Seattle, WA 98004, USA.
Mastropaolo
Donald
D
Hempel
Andrew
A
Camerman
Norman
N
D002243:Carbolines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005442:Flumazenil / Q000737:chemistry; D018757:GABA Modulators / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure
D002243:Carbolines; D018757:GABA Modulators; D005442:Flumazenil; C042568:ZK 93426