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.
Najjar
Fadia
F
Laboratoire de Synthèse et de Physicochimie de Molécules d'Intérêt Biologique, UMR CNRS 5068, Université Paul-Sabatier, 118 route de Narbonne, 31062 Toulouse, France.
Gorrichon
Liliane
L
Baltas
Michel
M
Vial
Henri
H
Tzedakis
Théodore
T
André-Barrès
Christiane
C
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