Synthesis and some properties of a homologous series of beta-carboline-3-carboxylic esters.
A homologous series of esters of beta-carboline-3-carboxylic acid was prepared by a new synthetic procedure. The first members of the series are convulsant or pro-convulsant agents while those with acyl residues longer than C4 show anticonvulsant activity. The affinity of the members of the series for the benzodiazepine receptor from rat brain decreases with the increasing chain length of the esters. The pentyl ester was studied in particular for its anti-convulsant effect on rats and mice treated with cardiazol. The compound also acts as a membrane stabilizer by inhibiting red cell hypotonic hemolysis and rat brain Na/K ATPase; its LD50 value is 12.5 mg/Kg and of particular interest is its lack of inhibitory effect on memory retention in mice at doses at which diazepam has inhibitory effects.
Centre De Recherche Inserm, Montpellier, France.
A
A
Previero
C
C
Castellano
R
R
Scuri
M
M
Bianchi
A A
AA
Rizzoli
L
L
Galzigna
D000818:Animals; D000927:Anticonvulsants / Q000138:chemical synthesis* / Q000633:toxicity; D001362:Avoidance Learning / Q000187:drug effects; D002243:Carbolines / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D055598:Chemical Phenomena; D002621:Chemistry; D004952:Esters / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity; D007928:Lethal Dose 50; D008297:Male; D051379:Mice; D051381:Rats
D000927:Anticonvulsants; D002243:Carbolines; D002264:Carboxylic Acids; D004952:Esters