New amino endoperoxides belonging to the antimalarial G-factor series

作者：Givelet Cecile; Bernat Virginie; Danel Mathieu; Andre Barres Christiane^*; Vial Henri

来源：European Journal of Organic Chemistry, 2007, (19): 3095-3101.

DOI：10.1002/ejoc.200700086

• endoperoxide
• malaria
• autoxidation
• hexacoordinate fluorosilicon complex
• 1,2-dioxetane

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.

• 出版日期2007-7