Construction and Docking Studies of Novel Pyrimido[4,5-b]quinolines as Antimicrobial Agents

Chem Biodivers. 2024 Jun;21(6):e202400200. doi: 10.1002/cbdv.202400200. Epub 2024 May 8.

Abstract

In order to develop novel antimicrobial agents, we prepared quinoline bearing pyrimidine analogues 2-7, 8 a-d and 9 a-d and their structures were elucidated by spectroscopic techniques. Furthermore, our second aim was to predict the interactions between the active compounds and enzymes (DNA gyrase and DHFR). In this work, fourteen pyrimido[4,5-b]quinoline derivatives were prepared and assessed for their antimicrobial potential by estimating zone of inhibition. All the screened candidates displayed antibacterial potential with zone of inhibition range of 9-24 mm compared with ampicillin (20-25 mm) as a reference drug. Moreover, the target derivatives 2 (ZI=16), 9 c (ZI=17 mm) and 9 d (ZI=16 mm) recorded higher antifungal activity against C. albicans to that exhibited by the antifungal drug amphotericin B (ZI=15 mm). Finally, the most potent pyrimidoquinoline compounds (2, 3, 8 c, 8 d, 9 c and 9 d) were docked inside DHFR and DNA gyrase active sites and they recorded excellent fitting within the active regions of DNA gyrase and DHFR. These outcomes revealed us that compounds (2, 3, 8 c, 8 d, 9 c and 9 d) could be lead compounds to discover novel antibacterial candidates.

Keywords: DNA gyrase; Dihydrofolate reductase (DHFR); antimicrobial potential; docking study and pyrimido[4,5-b]quinolines.

MeSH terms

  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Candida albicans* / drug effects
  • DNA Gyrase* / chemistry
  • DNA Gyrase* / metabolism
  • Dose-Response Relationship, Drug
  • Microbial Sensitivity Tests*
  • Molecular Docking Simulation*
  • Molecular Structure
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology
  • Quinolines* / chemistry
  • Quinolines* / pharmacology
  • Structure-Activity Relationship
  • Tetrahydrofolate Dehydrogenase* / chemistry
  • Tetrahydrofolate Dehydrogenase* / metabolism
  • Topoisomerase II Inhibitors / chemical synthesis
  • Topoisomerase II Inhibitors / chemistry
  • Topoisomerase II Inhibitors / pharmacology

Substances

  • Quinolines
  • DNA Gyrase
  • Tetrahydrofolate Dehydrogenase
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Pyrimidines
  • Topoisomerase II Inhibitors