López Rodriguez M L, Morcillo M J, Benito F, Benhamu B, Fernández E, Garrido M, Orensanz L
Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, Madrid, Spain.
Chem Pharm Bull (Tokyo). 1994 Oct;42(10):2108-12. doi: 10.1248/cpb.42.2108.
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.
（-）-（3,S）-6-羟基-1,2,3,4-四氢-β-咔啉-3-羧酸（3a）与异氰酸酯和异硫氰酸酯反应生成（±）-β-咔啉乙内酰脲（4a-d）和硫代乙内酰脲体系（5a-d）。用异氰酸酯处理（-）-（1S,3S）-6-羟基-1-甲基-1,2,3,4-四氢-β-咔啉-3-羧酸（3b）得到β-咔啉乙内酰脲环的（±）-顺式非对映异构体（4e-h）。然而，3b与异硫氰酸酯反应得到相应的反式异构体（5e-h）。这些结果已通过13C-NMR数据和核Overhauser效应（NOE）实验得到证实。对新化合物进行了体外与中枢型苯二氮䓬受体结合亲和力的测试。
