Synthesis and antimalarial activities of novel 3,3,6,6-tetraalkyl-1,2,4,5-tetraoxanes

Katja Zmitek; Stojan Stavber; Marko Zupan; Daniele Bonnet-Delpon; Sebastien Charneau; Phillipe Grellier; Jernej Iskra

doi:10.1016/j.bmc.2006.07.069

Synthesis and antimalarial activities of novel 3,3,6,6-tetraalkyl-1,2,4,5-tetraoxanes

Bioorg Med Chem. 2006 Dec 1;14(23):7790-5. doi: 10.1016/j.bmc.2006.07.069. Epub 2006 Aug 17.

Authors

Katja Zmitek¹, Stojan Stavber, Marko Zupan, Daniele Bonnet-Delpon, Sebastien Charneau, Phillipe Grellier, Jernej Iskra

Affiliation

¹ Laboratory of Organic and Bioorganic Chemistry, Jozef Stefan Institute and Faculty of Chemistry and Chemical Technology of University of Ljubljana, Jamova 39, 1000 Ljubljana, Slovenia.

PMID: 16919459
DOI: 10.1016/j.bmc.2006.07.069

Abstract

The oxidative system H2O2/fluorinated alcohol (TFE, HFIP) was used for direct acid- and MeReO3-catalyzed synthesis of 1,2,4,5-tetraoxanes from cyclic (C6, C7, and C12) and acyclic ketones. The influence of ring size and alkyl chain length were studied and antimalarial activities of synthetic 3,3,6,6-tetraalkyl-1,2,4,5-tetraoxanes were determined. Variations in their antimalarial activities were significant, although they share similar electrochemical properties of the peroxide bond.

Publication types

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

MeSH terms

Antimalarials / chemical synthesis*
Antimalarials / pharmacology
Catalysis
Hydrogen Peroxide
Ketones / chemistry
Oxidation-Reduction
Structure-Activity Relationship
Tetraoxanes / chemical synthesis
Tetraoxanes / pharmacology*

Substances

Antimalarials
Ketones
Tetraoxanes
Hydrogen Peroxide