Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain

Bioorg Med Chem Lett. 2003 Oct 20;13(20):3527-30. doi: 10.1016/s0960-894x(03)00756-x.

Abstract

While commercial isatins were practically inactive against the target proteases, thiosemicarbazone derivatives were found to be active. The most active compound from the series displayed an inhibitory IC(50) value of 1 microM against rhodesain. One thiosemicarbazone was found to be active against all three proteases with inhibitory IC(50) values of 10 microM or less. A combination of N-benzylation and appropriate substitution on the aromatic portion of the isatin scaffold was generally found to be beneficial especially against cruzain for ketone inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drug Evaluation, Preclinical
  • Isatin / chemical synthesis*
  • Isatin / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Protease Inhibitors / chemical synthesis*
  • Protease Inhibitors / pharmacology*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Thiosemicarbazones / chemical synthesis*
  • Thiosemicarbazones / pharmacology*

Substances

  • Protease Inhibitors
  • Thiosemicarbazones
  • Isatin