Quinine bis-conjugates with quinolone antibiotics and peptides: synthesis and antimalarial bioassay

Org Biomol Chem. 2012 Dec 7;10(45):8985-93. doi: 10.1039/c2ob26439k. Epub 2012 Oct 16.

Abstract

Benzotriazole-mediated syntheses led to novel bis-conjugates of quinine with quinolone antibiotics and amino acid linkers which were successfully prepared by two alternative routes with excellent yields and retention of chirality. These bis conjugates retain in vitro antimalarial activity with IC(50) values ranging from 12 to 207 nM, similar to quinine itself.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Antimalarials / chemical synthesis
  • Antimalarials / chemistry*
  • Antimalarials / pharmacology*
  • Chemistry Techniques, Synthetic
  • Inhibitory Concentration 50
  • Peptide Fragments / chemistry*
  • Plasmodium falciparum / drug effects
  • Quinine / chemical synthesis
  • Quinine / chemistry*
  • Quinine / pharmacology*
  • Quinolones / chemistry*
  • Triazoles / chemistry

Substances

  • Anti-Bacterial Agents
  • Antimalarials
  • Peptide Fragments
  • Quinolones
  • Triazoles
  • benzotriazole
  • Quinine