Synthesis of Fluorescent 1-(3-Amino-4-(4-(tert-butyl)phenyl)-6-(p-tolyl)furo[2,3-b]pyridin-2-yl)ethan-1-one: Crystal Structure, Fluorescence Behavior, Antimicrobial and Antioxidant Studies

J Fluoresc. 2018 Mar;28(2):655-662. doi: 10.1007/s10895-018-2227-2. Epub 2018 Apr 21.

Abstract

Furopyridine III, namely 1-(3-amino-4-(4-(tert-butyl)phenyl)-6-(p-tolyl)furo[2,3-b]pyridin-2-yl)ethan-1-one, synthesized from 4-(4-(tert-butyl)phenyl)-2-oxo-6-(p-tolyl)-1,2-dihydropyridine-3-carbonitrile I in two steps. The title compound is characterized by NMR, MS and its X-ray structure. The molecular structure consists of planar furopyridine ring with both phenyl rings being inclined from the furopyridine scaffold to a significant different extent. There are three intramolecular hydrogen bonds within the structure. The lattice is stabilized by N-H…O, H2C-H …π and π…π intermolecular interactions leading to three-dimensional network. Compound III exhibits fluorescent properties, which are investigated. Antimicrobial potential and antioxidant activity screening studies for the title compound III and the heterocyclic derivatives, I and II, show no activity towards neither bacterial nor fungal strains, while they exhibited weak to moderate antioxidant activity compared to reference.

Keywords: Antioxidant activity; Crystal structure; Fluorescence; Furo[2,3-b]pyridine.

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Biphenyl Compounds / chemistry
  • Chemistry Techniques, Synthetic
  • Crystallography, X-Ray
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology
  • Free Radical Scavengers / chemical synthesis
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Conformation
  • Picrates / chemistry
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / pharmacology*
  • Spectrometry, Fluorescence

Substances

  • 1-(3-amino-4-(4-(tert-butyl)phenyl)-6-(p-tolyl)furo(2,3-b)pyridin-2-yl)ethan-1-one
  • Anti-Infective Agents
  • Biphenyl Compounds
  • Fluorescent Dyes
  • Free Radical Scavengers
  • Picrates
  • Pyridines
  • 1,1-diphenyl-2-picrylhydrazyl