1-Substituted beta-carboline-3-carboxylates with high affinities to the benzodiazepine recognition site.
Naturally occurring derivatives of beta-carboline-3-carboxylic acid bearing acetyl or vinyl groups at C-1 were prepared by Pd-catalyzed cross-coupling reactions of methyl 1-chloro-beta-carboline-3-carboxylate with appropriate organostannanes. Esters with chloro or acetyl groups at C-1 showed high affinity for the brain benzodiazepine recognition site. Thus, in contrast to 1-alkyl and 1-aryl analogs, these beta-carboline-3-carboxylates with electron-withdrawing substituents at C-1 show high affinities.
Bracher
Franz
F
Department Pharmazie-Zentrum für Pharmaforschung, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 Munich, Germany. Franz.Bracher@cup.uni-muenchen.de
Hildebrand
Dirk
D
Häberlein
Hanns
H
D000818:Animals; D001569:Benzodiazepines; D002243:Carbolines / Q000138:chemical synthesis* / Q000494:pharmacology*; D002540:Cerebral Cortex / Q000187:drug effects; D008297:Male; D008517:Phytotherapy; D010946:Plants, Medicinal; D051381:Rats; D017208:Rats, Wistar; D011963:Receptors, GABA-A / Q000187:drug effects*
D002243:Carbolines; D011963:Receptors, GABA-A; D001569:Benzodiazepines