Abstract
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 methylenolethers. 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.
Key words
addition reactions - antitumor agents - diazo compounds - ketones - terpenoids
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CCDC 610293 contains the supplementary crystallographic data for this paper. These
data can be obtained free of charge from Cambridge Crystallographic Data Centre via
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12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk
