Chondramide Derivatives

In 1995 Höfle and Reichenbach reported the isolation of the chondramides, cyclodepsipeptides closely related to jaspla­kinolide and geodiamolide, mainly differing in the polyketide fragment. The chondramides where shown to bind to actin in an analogous manner like these peptides, what makes this sub­stances also highly interesting from a pharmaceutical point of view.

  • B. Kunze, R. Jansen, F. Sasse, G. Höfle, H. Reichenbach, J. Antibiot. 1995, 48, 1262–1266.
  • R. Jansen, B. Kunze, H. Reichenbach, G. Höfle, Liebigs Ann. 1996, 285–290.

Removing the methyl groups and the stereogenic centers from the ω-hydroxyacid of the chondramides results in a significant drop in the cytotoxicity of these interesting depsipeptides. This effect can be almost compensated by introduction of a second chlorine atom on the β-tyrosine moiety of the natural products. These simplified chondramides are much easier accessible than the natural chondramides.

  • D. Becker, U. Kazmaier, "Synthesis of Simplified Halogenated Chondramide Derivatives as new Actin-binding Agents", Eur. J. Org. Chem. 2015, 2591–2602.
  • D. Becker, U. Kazmaier, "Synthesis and Biological Evaluation of Dichlorinated Chondramide Derivatives", Eur. J. Org. Chem. 2015, 4198–4213.