Synthesis and anticonvulsant activity of some tetracyclic indole derivatives

J Med Chem. 1983 Jul;26(7):986-9. doi: 10.1021/jm00361a010.

Abstract

Several related series of cycloalkyl[4,5]pyrrolo[3,2,1-ij]quinolines 7a-g, 8a-c, 10a-3, and 16a-f and indolo[3,2,1-hi]indoles 22a-c and 23a,b were synthesized and tested for anticonvulsant activity. The key preparative step, a Fischer indole reaction between a bicyclic hydrazine and a cyclic ketone, gave the compounds in 34-96% yield. The products were tested in rat maximal electroshock for anticonvulsant activity. Several compounds showed good activity, with 6-[(dimethylamino)methyl]-4,5,6,8,9,10-hexahydrocyclopenta[4,5]pyrrolo[3,2,1-ij]quinoline (7d) and N-methyl-4,5,6,8,9,10,11,12-octahydrocyclohepta[4,5]pyrrolo[3,2,1-ij]quinoline- 6-carboxamide (10c) having ED50's of 12.5 and 12.9 mg/kg po, respectively.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Anticonvulsants / chemical synthesis*
  • Biological Assay
  • Electroshock
  • Indoles / chemical synthesis*
  • Indoles / therapeutic use
  • Magnetic Resonance Spectroscopy
  • Male
  • Rats
  • Rats, Inbred Strains
  • Seizures / drug therapy
  • Structure-Activity Relationship

Substances

  • Anticonvulsants
  • Indoles