A concise silylamine approach to 2-amino-3-hydroxy-indoles with potent in vivo antimalaria activity

Org Lett. 2010 Sep 17;12(18):3998-4001. doi: 10.1021/ol101566h.

Abstract

The development of a concise strategy to access 2-amino-3-hydroxy-indoles, which are disclosed as novel antimalarials with potent in vivo activity, is reported. Starting from isatins the target compounds are synthesized in 2 steps and in good yields via oxoindole intermediates by employing tert-butyldimethylsilyl amine (TBDMSNH(2)) as previously unexplored ammonia equivalent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Animals
  • Antimalarials / chemical synthesis*
  • Antimalarials / therapeutic use*
  • Indoles / chemical synthesis*
  • Indoles / therapeutic use
  • Malaria, Falciparum / drug therapy*
  • Mice
  • Molecular Structure
  • Plasmodium falciparum / drug effects
  • Silanes / chemistry*
  • Structure-Activity Relationship

Substances

  • Amines
  • Antimalarials
  • Indoles
  • Silanes
  • 3-hydroxyindole