Synthesis, Characterization and Bioassay of Novel Substituted 1-(3-(1,3-Thiazol-2-yl)phenyl)-5-oxopyrrolidines

Molecules. 2020 May 22;25(10):2433. doi: 10.3390/molecules25102433.

Abstract

Thiazole derivatives attract the attention of scientists both in the field of organic synthesis and bioactivity research due to their high biological activity. In the present study, thiazole ring was obtained by the interaction of 1-(4-(bromoacetyl)phenyl)-5-oxopyrrolidine-3-carboxylic acid with thiocarbamide or benzenecarbothioamide, as well as tioureido acid. A series of substituted 1-(3-(1,3-thiazol-2-yl)phenyl)-5-oxopyrrolidines with pyrrolidinone, thiazole, pyrrole, 1,2,4-triazole, oxadiazole and benzimidazole heterocyclic fragments were synthesized and their antibacterial properties were evaluated against Gram-positive strains of Staphylococcus aureus, Bacillus cereus, Listeria monocytogenes and Gram-negative Pseudomonas aeruginosa, Escherichia coli and Salmonella enterica enteritidis. The vast majority of compounds exhibited between twofold and 16-fold increased antibacterial effect against the test-cultures when compared with Oxytetracycline.

Keywords: biological activity; heterocycles; pyrrolidinones; thiazoles; triazoles.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Bacillus cereus / drug effects
  • Escherichia coli / drug effects
  • Escherichia coli / pathogenicity
  • Listeria monocytogenes / drug effects
  • Listeria monocytogenes / pathogenicity
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / chemistry*
  • Oxadiazoles / pharmacology
  • Pyrrolidines / chemical synthesis
  • Pyrrolidines / chemistry*
  • Pyrrolidines / pharmacology
  • Staphylococcus aureus / drug effects
  • Staphylococcus aureus / pathogenicity
  • Structure-Activity Relationship
  • Thiazoles / chemistry

Substances

  • Anti-Bacterial Agents
  • Oxadiazoles
  • Pyrrolidines
  • Thiazoles