Synthesis and antibacterial activity of C11, C12-cyclic urea analogues of ketolides

Bioorg Med Chem Lett. 2007 Sep 15;17(18):5013-8. doi: 10.1016/j.bmcl.2007.07.041. Epub 2007 Jul 31.

Abstract

C11, C12-cyclic urea analogues of ketolides were designed and synthesized by use of a novel ketene acetal intermediate. This intermediate enabled introduction of an amino group at C12 stereospecifically and in high yield. The resulting cyclic urea ketolides appear to have in vitro activity similar to that of telithromycin which contains a C11, C12 cyclic carbamate moiety. Some of the C2 fluorinated compounds have improved potency against erm-containing Streptococcus pyogenes.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology*
  • Ketolides / chemical synthesis*
  • Ketolides / chemistry
  • Ketolides / pharmacology*
  • Microbial Sensitivity Tests
  • Streptococcus pyogenes / drug effects
  • Urea / chemistry*

Substances

  • Anti-Bacterial Agents
  • Ketolides
  • Urea