Reaction of 6-hydroxytetrahydro-beta-carboline-3-carboxylic acids with isocyanates and isothiocyanates.
The reaction of (-)-(3,S)-6-hydroxy-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (3a) with isocyanates and isothiocyanates gave the (+/-)-beta-carboline-hydantoin (4a-d) and -thiohydantoin systems (5a-d). The treatment of (-)-(1S,3S)-6-hydroxy-1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-ca rbo xylic acid (3b) with isocyanates yielded the (+/-)-cis diastereomer of the beta-carboline-hydantoin rings (4e-h). However, the reaction of 3b with isothiocyanates provided the corresponding trans isomer (5e-h). These results have been confirmed by 13C-NMR data and nuclear Overhauser effect (NOE) experiments. The new compounds were tested for in vitro binding affinity to the central-type benzodiazepine receptors.
López Rodriguez
M L
ML
Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, Madrid, Spain.
Morcillo
M J
MJ
Benito
F
F
Benhamu
B
B
Fernández
E
E
Garrido
M
M
Orensanz
L
L
D000818:Animals; D002243:Carbolines / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D002491:Central Nervous System Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D017953:Isocyanates / Q000378:metabolism*; D017879:Isothiocyanates / Q000378:metabolism*; D008297:Male; D008968:Molecular Conformation; D051381:Rats; D017207:Rats, Sprague-Dawley; D011963:Receptors, GABA-A / Q000378:metabolism*
D002243:Carbolines; D002491:Central Nervous System Agents; D017953:Isocyanates; D017879:Isothiocyanates; D011963:Receptors, GABA-A