Synthesis, reactions, and biological activities of some new thieno[3,2-c]quinoline and pyrrolo[3,2-c]quinoline derivatives

Arch Pharm (Weinheim). 2014 Feb;347(2):142-52. doi: 10.1002/ardp.201300167. Epub 2013 Dec 30.

Abstract

2-Bromo-4-fluoroaniline (1) was condensed with ethyl 2-cyano-3-ethoxyacrylate (2) in ethanol to afford 3, which upon refluxing in paraffin oil at 250°C gave 8-bromo-3-cyano-6-fluoroquinoline-4(1H)-one (4). Then, compound 4 was taken as a versatile building block that allows the synthesis of thieno[3,2-c]quinoline, pyrrolo[3,2-c]quinoline, and N-methylpyrrolo[3,2-c]quinoline systems. The newly synthesized compounds and their derivatives were characterized by elemental analysis and spectroscopy (IR, (1)H NMR, (13)C NMR, and mass). Furthermore, some of these synthesized compounds were screened for their biological activities against various pathogenic bacterial and fungal strains. Our results demonstrate that most of the synthesized compounds possess a significant broad antibacterial activity against all strains of both gram-positive and gram-negative bacteria. In addition, compound 5 showed remarkable antifungal activity.

Keywords: Antimicrobial activity; Fluoroquinolone; Pyrrolo[3,2-c]quinolines; Thieno[3,2-c]quinolines.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / pharmacology*
  • Disk Diffusion Antimicrobial Tests
  • Drug Design
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Quinolines / chemical synthesis*
  • Quinolines / pharmacology*
  • Spectrophotometry, Infrared
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Quinolines