beta-Carbolines as benzodiazepine receptor ligands. 1. Synthesis and benzodiazepine receptor interaction of esters of beta-carboline-3-carboxylic acid.
Several esters of beta-carboline-3-carboxylic acid were synthesized and tested in respect to their affinity for the benzodiazepine receptor in bovine cortex membranes. Out of these derivatives, the methyl, ethyl, and n-propyl ester were clearly the most potent, while the n-butyl, benzyl, and 3-pyridylmethyl ester were considerably less active. Moreover, several beta-carboline-3-carboxylates with ethanol derivatives as ester alcohol components were all less active than the ethyl or n-propyl ester themselves. It is concluded that the affinity of beta-carboline-3-carboxylates to the benzodiazepine receptor is profoundly dependent on molecular size, as well as hydrophobic and electronic parameters of the ester alcohol component.
D000818:Animals; D002243:Carbolines / Q000138:chemical synthesis / Q000378:metabolism*; D002417:Cattle; D002540:Cerebral Cortex / Q000378:metabolism; D007211:Indoles / Q000378:metabolism*; D011956:Receptors, Cell Surface / Q000378:metabolism*; D011963:Receptors, GABA-A
D002243:Carbolines; D007211:Indoles; D011956:Receptors, Cell Surface; D011963:Receptors, GABA-A; C024915:beta-carboline-3-carboxylic acid ethyl ester; C028585:propyl beta-carboline-3-carboxylate; C036150:beta-carboline-3-carboxylic acid methyl ester