The effect of remote chirality on the antibacterial activity of indolinyl, tetrahydroquinolyl and dihydrobenzoxazinyl oxazolidinones

Bioorg Med Chem Lett. 2003 Dec 1;13(23):4235-9. doi: 10.1016/j.bmcl.2003.07.029.

Abstract

The oxazolidinones are promising agents for the treatment of infections caused by gram-positive bacteria, including multidrug-resistant strains. In ongoing studies we have discovered that a strategically placed chiral center of appropriate absolute configuration improves the antibacterial activity of indolinyl oxazolidinone analogues (gram-positive MIC's<0.5 microg/mL for the most potent congeners). The design, synthesis, antibacterial activity and pharmacokinetic profile of a selected series of alpha-methylated indoline derivatives and a related set of tetrahydroquinolyl and dihydrobenzoxazinyl analogues are discussed.

MeSH terms

  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / pharmacokinetics
  • Anti-Bacterial Agents* / pharmacology
  • Drug Design*
  • Drug Resistance, Bacterial
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Hydroquinones* / chemical synthesis
  • Hydroquinones* / pharmacokinetics
  • Hydroquinones* / pharmacology
  • Indoles* / chemical synthesis
  • Indoles* / pharmacokinetics
  • Indoles* / pharmacology
  • Microbial Sensitivity Tests
  • Oxazines* / chemical synthesis
  • Oxazines* / pharmacokinetics
  • Oxazines* / pharmacology
  • Oxazolidinones* / chemical synthesis
  • Oxazolidinones* / pharmacokinetics
  • Oxazolidinones* / pharmacology
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Hydroquinones
  • Indoles
  • Oxazines
  • Oxazolidinones