Structures and biological activity of three 2-(pyridin-2-yl)-1H-benzimidazole derivatives

Acta Crystallogr C Struct Chem. 2023 Dec 1;79(Pt 12):504-512. doi: 10.1107/S2053229623009452. Epub 2023 Nov 8.

Abstract

Two new 2-(pyridin-2-yl)-1H-benzimidazole derivatives, namely, 2-(4-phenoxypyridin-2-yl)-1H-benzimidazole, C18H13N3O, and 2-[4-(4-fluorophenoxy)pyridin-2-yl]-1H-benzimidazole, C18H12FN3O, were synthesized and characterized by NMR spectroscopy. Crystal structure, biological activity and ADME analyses were performed for these two new compounds and a third compound, namely, 5,6-dimethyl-2-[4-(4-phenylpiperazin-1-yl)pyridin-2-yl]-1H-benzimidazole methanol monosolvate, C24H25N5·CH3OH, the synthesis of which had been described previously. All three compounds have a similar chain hydrogen-bonding pattern. One of them (the fluorophenoxy derivative) showed good antimicrobial activity against Gram-positive bacteria. The ADME analysis indicates that the compounds could be good drug candidates.

Keywords: ADME; antibacterial activity; benzimidazole; crystal structure.

MeSH terms

  • Benzimidazoles*
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy

Substances

  • Benzimidazoles