One Pot Synthesis and Biological Activity Studies of New Spirooxindoles

Chem Biodivers. 2024 Jun;21(6):e202301942. doi: 10.1002/cbdv.202301942. Epub 2024 May 3.

Abstract

This article reports one-pot synthesis of ten novel spirooxindoles using 5-methyl-2-thiohydantoin, isatin derivatives, and malononitrile in good to high yields (65-90 %). The structures of the synthesized compounds were deduced by 1H-NMR, 13C NMR, FT-IR, and Mass spectral data. The antibacterial activity of the compounds was evaluated against two Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) based on the Kirby-Bauer method. According to the obtained data, the synthesized compounds show more activity against Gram-positive bacteria than Gram-negative bacteria. Also, the antioxidant activity of these compounds was measured using the DPPH radical scavenging test method, which showed good to excellent activity (59.65-94.03 %). Among them, the chlorinated derivatives (4 f-j) exhibited more antioxidant activity (84.85-94.03 %) than the other compounds (4 a-e) (56.65-74.4 %) and even ascorbic acid as a standard antioxidant compound (82.3 %).

Keywords: 2-Thiohydantoin; Anti-bacterial; Anti-oxidant; Isatins; Spirooxindoles.

MeSH terms

  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Antioxidants* / chemical synthesis
  • Antioxidants* / chemistry
  • Antioxidants* / pharmacology
  • Biphenyl Compounds / antagonists & inhibitors
  • Biphenyl Compounds / chemistry
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Indoles* / chemical synthesis
  • Indoles* / chemistry
  • Indoles* / pharmacology
  • Isatin / chemical synthesis
  • Isatin / chemistry
  • Isatin / pharmacology
  • Microbial Sensitivity Tests*
  • Molecular Structure
  • Oxindoles / chemical synthesis
  • Oxindoles / chemistry
  • Oxindoles / pharmacology
  • Picrates / antagonists & inhibitors
  • Pseudomonas aeruginosa / drug effects
  • Spiro Compounds* / chemical synthesis
  • Spiro Compounds* / chemistry
  • Spiro Compounds* / pharmacology
  • Spirooxindoles
  • Staphylococcus aureus / drug effects
  • Structure-Activity Relationship

Substances

  • 1,1-diphenyl-2-picrylhydrazyl
  • Anti-Bacterial Agents
  • Antioxidants
  • Biphenyl Compounds
  • Indoles
  • Oxindoles
  • Picrates
  • Spiro Compounds
  • Spirooxindoles
  • Isatin