Synthesis and biological evaluation of 4-oxoquinoline-3-carboxamides derivatives as potent anti-fibrosis agents

Bioorg Med Chem Lett. 2014 Dec 15;24(24):5666-5670. doi: 10.1016/j.bmcl.2014.10.071. Epub 2014 Oct 29.

Abstract

Thirty-one 4-oxoquinoline-3-carboxamides derivatives were synthesized and evaluated for their anti-fibrotic activities by the inhibition of TGF-β1-induced total collagen accumulation and anti-inflammatory activities by the inhibition of LPS-stimulated TNF-α production. Among them, three compounds (10a, 10l and 11g) exhibited potent inhibitory effects on both TGF-β1-induced total collagen accumulation and LPS-stimulated TNF-α production. Furthermore, oral administrations of 10l at a dose of 20 mg/kg/day for 4 weeks effectively alleviated lung inflammation and injury, and decreased lung collagen accumulation in bleomycin-induced pulmonary fibrosis model. Histopathological evaluation of lung tissue confirmed 10l as a potential, orally active agent for the treatment of pulmonary fibrosis.

Keywords: 4-Oxoquinoline-3-carboxamides; Anti-inflammatory; Collagen accumulation; Pulmonary fibrosis; TGF-β1; TNF-α.

Publication types

  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Quinolones / chemistry*
  • Animals
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / pharmacology*
  • Antibiotics, Antineoplastic / toxicity
  • Bleomycin / toxicity
  • Cells, Cultured
  • Collagen / metabolism
  • Lipopolysaccharides / pharmacology
  • Pneumonia / chemically induced
  • Pneumonia / drug therapy*
  • Pneumonia / pathology
  • Pulmonary Fibrosis / chemically induced
  • Pulmonary Fibrosis / drug therapy*
  • Pulmonary Fibrosis / pathology
  • Rats
  • Transforming Growth Factor beta1 / pharmacology
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • 4-Quinolones
  • Anti-Inflammatory Agents
  • Antibiotics, Antineoplastic
  • Lipopolysaccharides
  • Transforming Growth Factor beta1
  • Tumor Necrosis Factor-alpha
  • Bleomycin
  • Collagen