[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].
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.
Mondeshka
D
D
Chemisch-Technologische Hochschule, Sofia, Bulgarien.
Angelova
I
I
Ivanov
C B
CB
Ivanova
N S
NS
D000818:Animals; D000897:Anti-Ulcer Agents / Q000138:chemical synthesis; D001381:Azepines / Q000138:chemical synthesis* / Q000494:pharmacology; D004298:Dopamine / Q000378:metabolism; D018492:Dopamine Antagonists; D066298:In Vitro Techniques; D008297:Male; D014179:Neurotransmitter Uptake Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology*; D009638:Norepinephrine / Q000037:antagonists & inhibitors* / Q000378:metabolism; D051381:Rats; D011919:Rats, Inbred Strains; D012702:Serotonin Antagonists / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000897:Anti-Ulcer Agents; D001381:Azepines; D018492:Dopamine Antagonists; D014179:Neurotransmitter Uptake Inhibitors; D012702:Serotonin Antagonists; D004298:Dopamine; D009638:Norepinephrine
Racemische und optisch aktive 2-Chlorethylcarbamoyl-derivate des 7,8-Dimethoxy-1-phenyl-1H-3-benzazepins: Neue Strukturtypen von DA, NE und 5-HT Uptake Inhibitoren.