Synthesis and antibacterial studies of binaphthyl-based tripeptoids. Part 2

Bioorg Med Chem. 2010 Jul 1;18(13):4793-800. doi: 10.1016/j.bmc.2010.05.005. Epub 2010 Jun 2.

Abstract

A compact synthesis of 15 new binaphthyl-based dicationic tripeptoids and one biphenyl based dicationic tripeptoid is described. Fourteen of these tripeptoids resulted from variation of the C-2' ether substituent of the binaphthyl unit. An O-iso-butyl ether binaphthyl derivative was found to be the most active against Staphylococcus aureus (MIC 1.95 μg/mL). The biphenyl analogue also showed good activity against S. aureus (MIC 1.95 μg/mL). These compounds, however, were less active against four vancomycin-resistant strains of enterococci (VRE) than some of our previously developed compounds that had an O-iso-pentyl ether substituent on the binaphthyl unit and a C-2 L-Leu moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Enterococcus / drug effects
  • Microbial Sensitivity Tests
  • Naphthalenes / chemistry*
  • Peptoids / chemical synthesis
  • Peptoids / chemistry*
  • Peptoids / pharmacology
  • Staphylococcus aureus / drug effects
  • Vancomycin Resistance

Substances

  • Anti-Bacterial Agents
  • Naphthalenes
  • Peptoids
  • naphthalene