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.
Tryptophan (I) ergibt über (II) die Carbonsäureester (III), von denen (IIIa)‐(IIIc) mit Chloranil (IV) zu den im Titel genannten β‐Carbolinen (Va)‐(Vc) oxidiert werden.
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