Design, Synthesis and Antibacterial Evaluation of 1-[(1R,2S)-2-Fluorocyclopropyl]ciprofloxacin-1,2,4-triazole-5(4H)-thione Hybrids

Chem Biodivers. 2018 Oct;15(10):e1800261. doi: 10.1002/cbdv.201800261. Epub 2018 Oct 9.

Abstract

A new class of 1-[(1R,2S)-2-fluorocyclopropyl]ciprofloxacin (CPFX)-1,2,4-triazole-5(4H)-thione hybrids 6a - 6o was designed, synthesized and evaluated for their in vitro antibacterial activities against a panel of clinically important drug-sensitive and drug-resistant Gram-positive and Gram-negative pathogens. Our results revealed that all hybrids 6a - 6o had great potency against the tested strains, especially Gram-negative pathogens. The synthesized hybrids were more potent than the parent 1-[(1R,2S)-2-fluorocyclopropyl]CPFX (1) and comparable to CPFX and levofloxacin against the majority of the tested pathogens, worth to be further investigated.

Keywords: 1,2,4-triazole-5(4H)-thione; antibacterial activities; ciprofloxacin; quinolone; structure-activity relationship.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Bacteria / drug effects
  • Bacterial Infections / drug therapy
  • Ciprofloxacin / analogs & derivatives*
  • Ciprofloxacin / chemical synthesis
  • Ciprofloxacin / pharmacology*
  • Drug Design*
  • Halogenation
  • Humans
  • Microbial Sensitivity Tests
  • Structure-Activity Relationship
  • Thiones / chemical synthesis
  • Thiones / chemistry
  • Thiones / pharmacology
  • Triazoles / chemical synthesis
  • Triazoles / chemistry*
  • Triazoles / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Thiones
  • Triazoles
  • 1,2,4-triazole
  • Ciprofloxacin

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