New Amino Endoperoxides Belonging to the Antimalarial G-Factor Series

Autor:	Christiane André-Barrès, Virginie Bernat, Cécile Givelet, Henri Vial, Mathieu Danel
Rok vydání:	2007
Předmět:	chemistry.chemical_classification 1 2-Dioxetane Autoxidation Stereochemistry Organic Chemistry Hexacoordinate Diastereomer Aldehyde Decomposition chemistry.chemical_compound chemistry Reactivity (chemistry) Amine gas treating Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2007:3095-3101
ISSN:	1099-0690 1434-193X
DOI:	10.1002/ejoc.200700086
Popis:	In the search for new antimalarial endoperoxides we developed a direct route for the preparation of new amino compounds belonging to the G-factor series. During the synthesis, a significant difference in reactivity between two series of diastereoisomers was observed. The final amino endoperoxides were obtained with 58 to 70 % yields, depending on the starting amine, in the “anti” series, but with the “syn” diastereoisomers an unexpected rearrangement occurred during the deprotection step. This was attributed to a transient hexacoordinate fluorosilicon complex allowing the formation of a 1,2-dioxetane. Its decomposition gave aldehyde 12 and 4-hydroxybutan-2-one; these compounds were also identified when acidic conditions were used in the deprotection step. The anti amino compounds obtained were tested, but in vitro activities were found to be lower than initially expected, and fitted poorly with the previous biological hypothesis.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
Databáze:	OpenAIRE
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