Antimalarial Simplified 3-Aryltrioxanes:  Synthesis and Preclinical Efficacy/Toxicity Testing in Rodents

Journal of Medicinal Chemistry
2001.0

Abstract

A streamlined five-step chemical synthesis of rationally designed, simplified 3-aryltrioxane 8a is described. A noteworthy feature of this synthetic scheme is use of air rather than expensive molecular oxygen as the source of the pharmacologically critical peroxide unit in trioxane 8a. This simplified acetal trioxane carboxylic acid 8a is thermally stable, and it is hydrolytically stable in water even at 40 degrees C and pH 7.4 for at least 7 days. Preclinical evaluation of this water-soluble synthetic trioxane 8a in rodents shows it to have at least as good a therapeutic index (efficacy/toxicity) as that of water-soluble semisynthetic trioxane artelinic acid (5).

Knowledge Graph

Similar Paper

Antimalarial Simplified 3-Aryltrioxanes:  Synthesis and Preclinical Efficacy/Toxicity Testing in Rodents
Journal of Medicinal Chemistry 2001.0
Orally Active Antimalarial 3-Substituted Trioxanes:  New Synthetic Methodology and Biological Evaluation
Journal of Medicinal Chemistry 1998.0
Orally active amino functionalized antimalarial 1,2,4-trioxanes
Bioorganic & Medicinal Chemistry Letters 2004.0
Spiro and Dispiro-1,2,4-trioxolanes as Antimalarial Peroxides:  Charting a Workable Structure−Activity Relationship Using Simple Prototypes
Journal of Medicinal Chemistry 2005.0
Chemical Stability of the Peroxide Bond Enables Diversified Synthesis of Potent Tetraoxane Antimalarials
Journal of Medicinal Chemistry 2008.0
Orally Active, Hydrolytically Stable, Semisynthetic, Antimalarial Trioxanes in the Artemisinin Family
Journal of Medicinal Chemistry 1999.0
Anticancer and Antimalarial Efficacy and Safety of Artemisinin-Derived Trioxane Dimers in Rodents
Journal of Medicinal Chemistry 2004.0
Malaria-Infected Mice Are Cured by a Single Oral Dose of New Dimeric Trioxane Sulfones Which Are Also Selectively and Powerfully Cytotoxic to Cancer Cells
Journal of Medicinal Chemistry 2009.0
Iodine-catalyzed one-pot synthesis and antimalarial activity evaluation of symmetrically and asymmetrically substituted 3,6-diphenyl[1,2,4,5]tetraoxanes
Bioorganic & Medicinal Chemistry Letters 2009.0
Orally Active 1,2,4-Trioxanes:  Synthesis and Antimalarial Assessment of a New Series of 9-Functionalized 3-(1-Arylvinyl)-1,2,5-trioxaspiro[5.5]undecanes against Multi-Drug-Resistant Plasmodium yoelii nigeriensis in Mice
Journal of Medicinal Chemistry 2006.0