Synthesis of substituted N-aryl-N'-Sulfamoyloxazolidin-2-ones with potential antibacterial activity

Recent Pat Antiinfect Drug Discov. 2007 Jun;2(2):131-9. doi: 10.2174/157489107780832604.

Abstract

Three series of derived compounds of N, Aryl-N',Sulfamoyloxazolidin-2-ones were synthesized starting from chloro-sulfonylisocyanate (CSI) by carbomoylation, sulfamoylation and intramolecular cyclization reactions followed by methylation and heterocyclic reopening reactions. This later is based on a new hydrolysis method which uses a solid support, in order to obtain the correspondent amino-alcohols, which allowed isolating a new amino-alcohol ester. Measurements of the hydro-solubility by determination partition coefficient (log p) in water/octanol system were carried out by spectrophotometry. The antibacterial activities in vitro of some synthesized compounds were evaluated on a "Staphylococus aureus" strain in a Mûller-Hintone medium, showing good activity for some of them. All the synthesized compounds are characterized by IR, (1)H NMR and mass spectroscopy (ESI-MS).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Chemical Phenomena
  • Chemistry, Physical
  • Indicators and Reagents
  • Methylation
  • Microbial Sensitivity Tests
  • Oxazolidinones / chemical synthesis*
  • Oxazolidinones / chemistry
  • Oxazolidinones / pharmacology*
  • Solubility
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared
  • Staphylococcus aureus / drug effects
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Indicators and Reagents
  • Oxazolidinones
  • Sulfonamides