Design, synthesis, in vitro and in silico characterization of new 2-quinolone-L-alaninate-1,2,3-triazoles as novel antimicrobial agents

Oussama Moussaoui*, Bhadane Rajendra, Riham Sghyar, Janez Ilaš, El Mestafa El Hadrami, Said Chakroune, Outi Salo-Ahen*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

4 Citations (Scopus)
27 Downloads (Pure)

Abstract

Due to the ever-increasing antimicrobial resistance there is an urgent need to continuously design and develop novel antimicrobial agents. Inspired by the broad antibacterial activities of various heterocyclic compounds such as 2-quinolone derivatives, we designed and synthesized new methyl-(2-oxo-1,2-dihydroquinolin-4-yl)-L-alaninate-1,2,3-triazole derivatives via 1,3-dipolar cycloaddition reaction of 1-propargyl-2-quinolone-L-alaninate with appropriate azide groups. The synthesized compounds were obtained in good yield ranging from 75 to 80 %. The chemical structures of these novel hybrid molecules were determined by spectroscopic methods and the antimicrobial activity of the compounds was investigated against both bacterial and fungal strains. The tested compounds showed significant antimicrobial activity and weak to moderate antifungal activity. Despite the evident similarity of the quinolone moiety of our compounds with fluoroquinolones, our compounds do not function by inhibiting DNA gyrase. Computational characterization of the compounds shows that they have attractive physicochemical and pharmacokinetic properties and could serve as templates for developing potential antimicrobial agents for clinical use.
Original languageEnglish
Article numbere202100714
JournalChemMedChem
Volume17
Issue number5
DOIs
Publication statusPublished - 4 Mar 2022
MoE publication typeA1 Journal article-refereed

Keywords

  • Antimicrobial resistance (AMR)
  • 2-quinolone
  • DNA gyrase
  • Quantum mechanics (QM)
  • Molecular dynamics (MD)

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