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

Farmaco. 1990 May;45(5):545-58.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding, Competitive / drug effects
  • Brain Chemistry / drug effects
  • Chemical Phenomena
  • Chemistry
  • In Vitro Techniques
  • Male
  • Psychotropic Drugs / chemical synthesis*
  • Pyrroles / chemical synthesis*
  • Pyrroles / metabolism
  • Pyrroles / pharmacology
  • Rats
  • Rats, Inbred Strains
  • Receptors, GABA-A / drug effects
  • Receptors, GABA-A / metabolism*
  • Synaptic Membranes / metabolism
  • Thiazepines / chemical synthesis*
  • Thiazepines / metabolism
  • Thiazepines / pharmacology

Substances

  • Psychotropic Drugs
  • Pyrroles
  • Receptors, GABA-A
  • Thiazepines
  • 7-acetoxy-6,7-dihydro-6-(4-methoxyphenyl)pyrrolo(2,1-d)(1,5)benzothiazepine
  • 6-(4-methoxyphenyl)pyrrolo(2,1-d)(1,5)benzothiazepin-7(6H)-ol