Synthesis, anti-bacterial, anti-asthmatic and anti-diabetic activities of novel N-substituted-2-(4-phenylethynyl-phenyl)-1H-benzimidazoles and N-substituted 2[4-(4,4-dimethyl-thiochroman-6-yl-ethynyl)-phenyl)-1H-benzimidazoles

Eur J Med Chem. 2008 May;43(5):986-95. doi: 10.1016/j.ejmech.2007.06.013. Epub 2007 Jul 10.

Abstract

Synthesis of a series of novel and functionalized benzimidazole derivatives by the condensation of OPDA with 4-bromobenzoic acid and subsequent reactions of the product obtained with phenylacetylene and 6-ethynyl-4,4-dimethylthiochroman utilising Sonogashira coupling has been reported. The Sonogashira coupling products were then alkylated at the benzimidazole -NH with different electrophilic reagents leading to functionalized derivatives. All the compounds synthesized were screened for their potential anti-bacterial, anti-asthmatic and anti-diabetic properties, which exhibited moderate activities in screening studies in vitro.

MeSH terms

  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Alkynes / pharmacology
  • Anti-Asthmatic Agents / chemical synthesis*
  • Anti-Asthmatic Agents / chemistry
  • Anti-Asthmatic Agents / pharmacology
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology
  • Dipeptidyl-Peptidase IV Inhibitors
  • Heterocyclic Compounds, 2-Ring / chemical synthesis*
  • Heterocyclic Compounds, 2-Ring / chemistry
  • Heterocyclic Compounds, 2-Ring / pharmacology
  • Humans
  • Hypoglycemic Agents / chemical synthesis*
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / pharmacology
  • Phosphodiesterase 4 Inhibitors
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors
  • Structure-Activity Relationship

Substances

  • Alkynes
  • Anti-Asthmatic Agents
  • Anti-Bacterial Agents
  • Benzimidazoles
  • Dipeptidyl-Peptidase IV Inhibitors
  • Heterocyclic Compounds, 2-Ring
  • Hypoglycemic Agents
  • Phosphodiesterase 4 Inhibitors
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1