Antiarrhythmic, serotonin antagonist and antianxiety activities of novel substituted thiophene derivatives synthesized from 2-amino-4,5,6,7-tetrahydro-N-phenylbenzo[b]thiophene-3-carboxamide

Eur J Med Chem. 2010 Dec;45(12):5935-42. doi: 10.1016/j.ejmech.2010.09.059. Epub 2010 Oct 14.

Abstract

A series of novel thiophene derivatives 3-17 were synthesized by initial reactions of 2-amino-4,5,6,7-tetrahydro-N-phenylbenzo[b]thiophene-3-carboxamide 1 and 2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carbonitrile 7 with different organic reagents. The structures of newly synthesized compounds were confirmed by IR, 1H NMR, MS spectral data and elemental analysis. Initially the acute toxicity of the compounds was assayed via the determination of their LD50. All the compounds were screened for their antiarrhythmic, serotonin antagonist and antianexiety activities and they showed high activity compared with procaine amide, lidocaine, diazepam and buspirone as positive controls. The detailed synthesis, spectroscopic data, LD50 and pharmacological activities of the synthesized compounds were reported.

MeSH terms

  • Animals
  • Anti-Anxiety Agents / chemical synthesis
  • Anti-Anxiety Agents / chemistry
  • Anti-Anxiety Agents / pharmacology*
  • Anti-Arrhythmia Agents / chemical synthesis
  • Anti-Arrhythmia Agents / chemistry
  • Anti-Arrhythmia Agents / pharmacology*
  • Male
  • Mice
  • Molecular Structure
  • Motor Activity / drug effects*
  • Rats
  • Rats, Wistar
  • Serotonin Antagonists / chemical synthesis
  • Serotonin Antagonists / chemistry
  • Serotonin Antagonists / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Thiophenes / chemical synthesis
  • Thiophenes / chemistry
  • Thiophenes / pharmacology*

Substances

  • Anti-Anxiety Agents
  • Anti-Arrhythmia Agents
  • Serotonin Antagonists
  • Thiophenes