One-pot synthesis and pharmacological evaluation of new quinoline/pyrimido-diazepines as pulmonary antifibrotic agents

Future Med Chem. 2024;16(21):2211-2230. doi: 10.1080/17568919.2024.2394018. Epub 2024 Sep 18.

Abstract

Aim: Pulmonary fibrosis is a life threating disease which requires an immediate treatment and due to the limited medications, this study focused on synthesizing a series of quinoline-based pyrimidodiazepines 4a-f as a novel antifibrotic hit.Materials & methods: The target compounds were synthesized via a one-pot reaction then investigated in a rat model of lung fibrosis induced by bleomycin (BLM).Results: Results revealed significant attenuation of the tested pro-inflammatory cytokines, fibrotic genes and apoptotic markers; however, Bcl-2 was upregulated, indicating a protective effect against fibrosis. Moreover, the molecular docking studies highlighted promising interactions between compounds 4b and 4c and specific amino acids within the protein pockets of caspase-3 (ARG341 and THR177), malondialdehyde (LYS195, LYS118 and ARG188) and TNF-α (SER99 and NME102).Conclusion: Compounds 4b and 4c emerge as promising candidates for further preclinical investigation as pulmonary antifibrotic agents.

Keywords: BLM; antifibrotic; one-pot synthesis; pulmonary fibrosis; pyrimidodiazepines.

Plain language summary

[Box: see text].

MeSH terms

  • Animals
  • Antifibrotic Agents* / chemical synthesis
  • Antifibrotic Agents* / chemistry
  • Antifibrotic Agents* / pharmacology
  • Apoptosis / drug effects
  • Azepines* / chemical synthesis
  • Azepines* / chemistry
  • Azepines* / pharmacology
  • Bleomycin* / pharmacology
  • Lung / drug effects
  • Lung / metabolism
  • Lung / pathology
  • Male
  • Molecular Docking Simulation*
  • Molecular Structure
  • Pulmonary Fibrosis* / chemically induced
  • Pulmonary Fibrosis* / drug therapy
  • Pulmonary Fibrosis* / metabolism
  • Pulmonary Fibrosis* / pathology
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology
  • Quinolines* / chemical synthesis
  • Quinolines* / chemistry
  • Quinolines* / pharmacology
  • Rats
  • Structure-Activity Relationship

Substances

  • Quinolines
  • Antifibrotic Agents
  • Azepines
  • Bleomycin
  • Pyrimidines
  • quinoline