New Library of Iodo-Quinoline Derivatives Obtained by an Alternative Synthetic Pathway and Their Antimicrobial Activity

Molecules. 2024 Feb 7;29(4):772. doi: 10.3390/molecules29040772.

Abstract

6-Iodo-substituted carboxy-quinolines were obtained using a one-pot, three-component method with trifluoroacetic acid as a catalyst under acidic conditions. Iodo-aniline, pyruvic acid and 22 phenyl-substituted aldehydes (we varied the type and number of radicals) or O-heterocycles, resulting in different electronic effects, were the starting components. This approach offers advantages such as rapid response times, cost-effective catalysts, high product yields and efficient purification procedures. A comprehensive investigation was conducted to examine the impact of aldehyde structure on the synthesis pathway. A library of compounds was obtained and characterized by FT-IR, MS, 1H NMR and 13C NMR spectroscopy and single-ray crystal diffractometry. Their antimicrobial activity against S. epidermidis, K. pneumonie and C. parapsilosis was tested in vitro. The effect of iodo-quinoline derivatives on microbial adhesion, the initial stage of microbial biofilm development, was also investigated. This study suggests that carboxy-quinoline derivatives bearing an iodine atom are interesting scaffolds for the development of novel antimicrobial agents.

Keywords: C. parapsilosis; Doebner synthesis; K. pneumonie; S. epidermidis; antimicrobial activity; iodo-quinolines.

MeSH terms

  • Anti-Infective Agents* / chemistry
  • Iodine*
  • Quinolines* / chemistry
  • Spectroscopy, Fourier Transform Infrared

Substances

  • quinoline
  • Anti-Infective Agents
  • Iodine
  • Quinolines

Grants and funding

This research received no external funding.