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 hexacoord...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2004-03, Vol.14 (6), p.1433-1436
Main Authors: Najjar, Fadia, Gorrichon, Liliane, Baltas, Michel, Vial, Henri, Tzedakis, Théodore, André-Barrès, Christiane
Format: Article
Language:English
Subjects:
Animals
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antimalarials - chemistry
Antimalarials - pharmacology
Antiparasitic agents
Biological and medical sciences
Carboxylic Acids - chemistry
Electrochemistry
Endoperoxides
G-factor
Hexacoordinated silicon compounds
Malaria
Medical sciences
Pharmacology. Drug treatments
Plant Growth Regulators - chemistry
Plant Growth Regulators - pharmacology
Plasmodium falciparum - drug effects
Plasmodium falciparum - growth & development
Prostaglandin Endoperoxides, Synthetic - chemical synthesis
Prostaglandin Endoperoxides, Synthetic - pharmacology
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Summary: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. During synthesis of endoperoxides exhibiting antimalarial activity due to the peroxyketal function, a novel rearrangement occurred providing heterocycle 9.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2004.01.024