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[Racemic and optically active 2-chloroethylcarbamoyl derivatives of 7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine: a new structural type of DA, NE and 5-T uptake inhibitors].
- Source :
-
Archiv der Pharmazie [Arch Pharm (Weinheim)] 1990 Oct; Vol. 323 (10), pp. 829-32. - Publication Year :
- 1990
-
Abstract
- The racemic and optically active 2-chloroethylcarbamoyl derivatives of 7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines 6 and 8 were synthesized. The enantiomers of the benzazepine 5 were obtained by consecutive treatment of (+/-)-5 with (-) and (+)-dibenzoyl-tartaric acids. Compounds 6 are strong DA and NE uptake inhibitors while 8 exhibits inhibition towards 5-HT. The inhibitory effect of 6 is characterized by clearly expressed enantioselectivity. So 1-S-6 is a 26, resp. a 40 times stronger inhibitor of DA and NE uptake than 1-S-6. (+/-)-6 shows moderate antiulcer activity on water-immersion stress ulcer.
- Subjects :
- Animals
Anti-Ulcer Agents chemical synthesis
Azepines pharmacology
Dopamine metabolism
In Vitro Techniques
Male
Neurotransmitter Uptake Inhibitors chemical synthesis
Norepinephrine metabolism
Rats
Rats, Inbred Strains
Stereoisomerism
Structure-Activity Relationship
Azepines chemical synthesis
Dopamine Antagonists
Neurotransmitter Uptake Inhibitors pharmacology
Norepinephrine antagonists & inhibitors
Serotonin Antagonists chemistry
Subjects
Details
- Language :
- German
- ISSN :
- 0365-6233
- Volume :
- 323
- Issue :
- 10
- Database :
- MEDLINE
- Journal :
- Archiv der Pharmazie
- Publication Type :
- Academic Journal
- Accession number :
- 2150477
- Full Text :
- https://doi.org/10.1002/ardp.19903231003