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

doi:10.1248/cpb.53.653

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

Research output: Contribution to journal › Article › peer-review

45 Citations (Scopus)

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.

Original language	English
Pages (from-to)	653-661
Number of pages	9
Journal	Chemical and Pharmaceutical Bulletin
Volume	53
Issue number	6
DOIs	https://doi.org/10.1248/cpb.53.653
Publication status	Published - Jun 2005

Keywords

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1248/cpb.53.653

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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.",

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AU - Takasu, Kiyosei

AU - Shimogama, Tsubasa

AU - Saiin, Chalerm

AU - Kim, Hye Sook

AU - Wataya, Yusuke

AU - Brun, Reto

AU - Ihara, Masataka

PY - 2005/6

Y1 - 2005/6

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KW - Antimalarial agent

KW - Structure-activity relationship

KW - Total synthesis

KW - Tropical disease

KW - β-Carbolinium salt

KW - π-delocalized lipophilic cationic (DLC) hypothesis

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

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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