Synthesis and Antibacterial Activity of New Thiazolidine-2,4-dione-Based Chlorophenylthiosemicarbazone Hybrids

Molecules. 2018 Apr 26;23(5):1023. doi: 10.3390/molecules23051023.

Abstract

Series of new thiazolidine-2,4-dione-based chlorophenylthiosemicarbazone hybrids (1740) were synthesized by the reaction of condensation chlorophenylthiosemicarbazides with formylphenyl 2-(2,4-dioxothiazolidin-5-yl/ylidene)acetates. New compounds were tested on reference strains of Gram-positive and Gram-negative bacteria. The antibacterial activity of target compounds was determined by broth dilution method. Most active compounds possess minimum inhibitory concentration (MIC) = 3.91 mg/L. These compounds were non-toxic at concentrations close to their antibacterial effect. The antibacterial activity of some compounds was similar to or higher than the activity of used reference drugs such as oxacillin and cefuroxime. The structure⁻activity relationships (SARs) analysis collectively suggests that at least two different molecular mechanisms of their antibacterial activity should be expected.

Keywords: antibacterial activity; chlorophenylthiosemicarbazones; thiazolidine-2,4-dione.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Structure-Activity Relationship
  • Sulfur Compounds / chemical synthesis*
  • Sulfur Compounds / chemistry
  • Sulfur Compounds / pharmacology
  • Thiazolidinediones / chemistry*
  • Thiosemicarbazones / chemistry*

Substances

  • Anti-Bacterial Agents
  • Sulfur Compounds
  • Thiazolidinediones
  • Thiosemicarbazones
  • thiazolidine-2,4-dione