Synthesis and Evaluation of β-Carbolinium Cations as New Antimalarial Agents Based on π-Delocalized Lipophilic Cation (DLC) Hypothesis

• Takasu Kiyosei

  Graduate School of Pharmaceutical Sciences, Tohoku University

• Shimogama Tsubasa

  Graduate School of Pharmaceutical Sciences, Tohoku University

• Saiin Chalerm

  Graduate School of Pharmaceutical Sciences, Tohoku University

• Kim Hye-Sook

  Faculty of Pharmaceutical Sciences, Okayama University

• Wataya Yusuke

  Faculty of Pharmaceutical Sciences, Okayama University

• Brun Reto

  Swiss Tropical Institute

• Ihara Masataka

  Graduate School of Pharmaceutical Sciences, Tohoku University

Bibliographic Information

Other Title

• Synthesis and Evaluation of ベータ Carbolinium Cations as New Antimalarial Agents Based on パイ Delocalized Lipophilic Cation DLC Hypothesis
• Synthesis and Evaluation of β-Carbolinium Cations as New Antimalarial Agents Based on π-Delocalized Lipophilic Cation (DLC) Hypothesis

Abstract

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.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 53 (6), 653-661, 2005

  The Pharmaceutical Society of Japan

Keywords

• antimalarial agent
• β-carbolinium salt
• total synthesis
• π-delocalized lipophilic cationic (DLC) hypothesis
• tropical disease
• structure–activity relationship

Details

• CRID: 1390001204169124480
• NII Article ID: 10016654331
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.53.653
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 7318466
• PubMed: 15930777
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I7318466
• Web Site: https://www.jstage.jst.go.jp/article/cpb/53/6/53_6_653/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2006205602
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
• Abstract License Flag: Disallowed