Research on compounds with psychotropic activity. IX--Synthesis of 6-p-methoxyphenylpyrrolo[2,1-d][1,5]benzothiazepines and evaluation of their affinities for BDZ and GABA receptor subtypes.
6-p-Methoxyphenylpyrrolo[2,1-d][1,5]benzothiazepin-7(6H)-one (IV), cis-7-acetoxy-6,7-dihydro-6-p-methoxyphenylpyrrolo[2,1-d] [1,5]benzothiazepine (V) and some significant 7-acyloxy-6-p-methoxyphenylpyrrolo[2,1-d][1,5]benzothiazepines (VI a-g) were synthesized and tested in vitro for inhibition of the specific binding of 3H-Flunitrazepam, 3H-PK 11195, 3H-Muscimol and 3H-(-)Baclofen to central and peripheral benzodiazepine, GABA-A and GABA-B receptors, respectively. The compounds (IV), VI a) and (VI c) were active on the peripheral benzodiazepine receptor; in particular (VI a) and (VI c) were very active. The compound (VI g) showed an affinity, even though scanty, for the central benzodiazepine receptor.
Nacci
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V
Dipartimento Farmaco Chimico Tecnologico, Università di Siena, Italy.
Fiorini
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I
Garofalo
A
A
Cagnotto
A
A
D000818:Animals; D001667:Binding, Competitive / Q000187:drug effects; D001923:Brain Chemistry / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D066298:In Vitro Techniques; D008297:Male; D011619:Psychotropic Drugs / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D051381:Rats; D011919:Rats, Inbred Strains; D011963:Receptors, GABA-A / Q000187:drug effects / Q000378:metabolism*; D013570:Synaptic Membranes / Q000378:metabolism; D013841:Thiazepines / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology
D011619:Psychotropic Drugs; D011758:Pyrroles; D011963:Receptors, GABA-A; D013841:Thiazepines; C066209:7-acetoxy-6,7-dihydro-6-(4-methoxyphenyl)pyrrolo(2,1-d)(1,5)benzothiazepine; C066208:6-(4-methoxyphenyl)pyrrolo(2,1-d)(1,5)benzothiazepin-7(6H)-ol