Crucial role of the peroxyketal function for antimalarial activity in the G-factor series.
New endoperoxides, related to the natural phytohormones known as G factors (G1, G2, G3), were modified on the side chain and the ketalic position. An unexpected rearrangement, specific to one diastereoisomer was observed in the deprotection step of O-silylated compounds and attributed to a hexacoordinated fluorosilicon intermediate. The reduction potential of these new peroxides was determined. They exhibited good to moderate antimalarial activity, greatly related to the presence of peroxyketal function.
Laboratoire de Synthèse et de Physicochimie de Molécules d'Intérêt Biologique, UMR CNRS 5068, Université Paul-Sabatier, 118 route de Narbonne, 31062 Toulouse, France.
Fadia
F
Najjar
Liliane
L
Gorrichon
Michel
M
Baltas
Henri
H
Vial
Théodore
T
Tzedakis
Christiane
C
André-Barrès
D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000494:pharmacology*; D002264:Carboxylic Acids / Q000737:chemistry; D004563:Electrochemistry; D010937:Plant Growth Regulators / Q000737:chemistry / Q000494:pharmacology*; D010963:Plasmodium falciparum / Q000187:drug effects / Q000254:growth & development; D011450:Prostaglandin Endoperoxides, Synthetic / Q000138:chemical synthesis / Q000494:pharmacology
D000962:Antimalarials; D002264:Carboxylic Acids; D010937:Plant Growth Regulators; D011450:Prostaglandin Endoperoxides, Synthetic