Synthesis and evaluation of β-carbolinium cations as new antimalarial agents based on π-delocalized lipophilic cation (DLC) hypothesis

Kiyosei Takasu, Tsubasa Shimogama, Chalerm Saiin, Hye Sook Kim, Yusuke Wataya, Reto Brun, Masataka Ihara

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38 Citations (Scopus)


Several β-carbolines including naturally occurring substances and their corresponding cationic derivatives were synthesized and evaluated for antimalarial (antiplasmodial) activity in vitro and in vivo. A tetracyclic carbolinium salt was elucidated for antileishmanial and antitrypanosomal activities in vitro as well as antiplasmodial activity. Quarternary carbolinium cations showed much higher potencies in vitro than electronically neutral β-carbolines and a good correlation was observed between π-delocalized lipophilic cationic (DLC) structure and antimalarial efficacy. β-Carbolinium compounds exhibit medium suppressive activity in vivo against rodent malaria.

Original languageEnglish
Pages (from-to)653-661
Number of pages9
JournalChemical and Pharmaceutical Bulletin
Issue number6
Publication statusPublished - Jun 1 2005



  • Antimalarial agent
  • Structure-activity relationship
  • Total synthesis
  • Tropical disease
  • β-Carbolinium salt
  • π-delocalized lipophilic cationic (DLC) hypothesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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