Synthesis and antimalarial activities of novel 3,3,6,6-tetraalkyl-1,2,4,5-tetraoxanes.
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.
Zmitek
Katja
K
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.
Stavber
Stojan
S
Zupan
Marko
M
Bonnet-Delpon
Daniele
D
Charneau
Sebastien
S
Grellier
Phillipe
P
Iskra
Jernej
J
D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology; D002384:Catalysis; D006861:Hydrogen Peroxide; D007659:Ketones / Q000737:chemistry; D010084:Oxidation-Reduction; D013329:Structure-Activity Relationship; D045568:Tetraoxanes / Q000138:chemical synthesis / Q000494:pharmacology*
D000962:Antimalarials; D007659:Ketones; D045568:Tetraoxanes; D006861:Hydrogen Peroxide