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Reactions of activated lupane oxo-compounds with diazomethane: An approach to new derivatives of cytotoxic triterpenes

Publikace na Přírodovědecká fakulta |
2006

Tento text není v aktuálním jazyce dostupný. Zobrazuje se verze "en".Abstrakt

The reactions of diazomethane with activated carbonyl derivatives of lupane were investigated. Previously known cytotoxic oxo-compounds were chosen as substrates, which allowed new information on the structure-activity relationships of this group of compounds to be obtained.

Reactions of lupane derivatives containing an unsaturated aldehyde, α-diketones or 18,19-seco-triketones with diazomethane gave 1,3-dipolar and carbene addition products, for example oxirane and dihydropyrazole derivatives, along with products arising from homologation of cyclic ketones, such as methylenoleth-ers. We synthesised seventeen new compounds containing dihydropyrazole, oxirane, cyclopropane or 3-methoxycyclohex-2-en-1-one rings on the triterpenic skeleton.

All compounds were tested for their in vitro cytotoxic activity against the T-lymphoblastic leukaemia CEM cell line.