Synthesis and in vitro antiprotozoal activities of water-soluble, inexpensive 3,7-bis(dialkylamino)phenoxazin-5-ium derivatives

Jian-Feng Ge; Chika Arai; Marcel Kaiser; Sergio Wittlin; Reto Brun; Masataka Ihara

doi:10.1021/jm8003619

Synthesis and in vitro antiprotozoal activities of water-soluble, inexpensive 3,7-bis(dialkylamino)phenoxazin-5-ium derivatives

J Med Chem. 2008 Jun 26;51(12):3654-8. doi: 10.1021/jm8003619. Epub 2008 May 14.

Authors

Jian-Feng Ge¹, Chika Arai, Marcel Kaiser, Sergio Wittlin, Reto Brun, Masataka Ihara

Affiliation

¹ Institute of Medicinal Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan.

PMID: 18476684
DOI: 10.1021/jm8003619

Abstract

3,7-Bis(dialkylamino)phenoxazinium salts were synthesized and evaluated for in vitro activities against Plasmodium falciparum, Trypanosoma cruzi, T. brucei rhodesiense, and Leishmania donovani. Notably, the compounds showed potent antiprotozoal activities, especially against P. falciparum and T. cruzi. The compounds with alkyl side chains less than three carbons in length possessed good activities with high selective indices.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antimalarials / chemical synthesis
Antimalarials / chemistry
Antimalarials / pharmacology
Antiprotozoal Agents / chemical synthesis*
Antiprotozoal Agents / chemistry
Antiprotozoal Agents / pharmacology
Chloroquine / pharmacology
Drug Resistance
Leishmania donovani / drug effects
Oxazines / chemical synthesis*
Oxazines / chemistry
Oxazines / pharmacology
Parasitic Sensitivity Tests
Plasmodium falciparum / drug effects
Pyrimethamine / pharmacology
Structure-Activity Relationship
Trypanocidal Agents / chemical synthesis
Trypanocidal Agents / chemistry
Trypanocidal Agents / pharmacology
Trypanosoma brucei rhodesiense / drug effects
Trypanosoma cruzi / drug effects

Substances

Antimalarials
Antiprotozoal Agents
Oxazines
Trypanocidal Agents
Chloroquine
Pyrimethamine