A domino reaction of 3-chlorochromones with aminoheterocycles. Synthesis of pyrazolopyridines and benzofuropyridines and their optical and ecto-5'-nucleotidase inhibitory effects

Org Biomol Chem. 2018 Jan 31;16(5):717-732. doi: 10.1039/c7ob02729j.

Abstract

A new and efficient domino reaction of 3-chlorochromones with electron-rich aminoheterocycles was developed which allows for a convenient synthesis of a variety of pyrazolo[3,4-b]pyridines, pyrrolo[2,3-b]pyridines, pyrido[2,3-d]pyrimidines and benzofuro[3,2-b]pyridines. The products exhibit strong fluorescence. In addition, they exhibit significant ecto-5'-nucleotidase inhibition properties and cytotoxic behavior.

MeSH terms

  • 5'-Nucleotidase / antagonists & inhibitors*
  • 5'-Nucleotidase / chemistry
  • 5'-Nucleotidase / metabolism
  • Amines / chemical synthesis
  • Amines / chemistry
  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry
  • Benzene Derivatives / pharmacology*
  • Cell Survival / drug effects
  • Chromones / chemical synthesis
  • Chromones / chemistry
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • GPI-Linked Proteins / antagonists & inhibitors
  • GPI-Linked Proteins / chemistry
  • GPI-Linked Proteins / metabolism
  • Halogenation
  • HeLa Cells
  • Humans
  • Molecular Docking Simulation
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / pharmacology*

Substances

  • Amines
  • Benzene Derivatives
  • Chromones
  • Enzyme Inhibitors
  • GPI-Linked Proteins
  • Pyrazoles
  • Pyridines
  • pyrazolopyridine
  • 5'-Nucleotidase
  • NT5E protein, human