Labelled compounds of interest as antitumour agents-VII1. [2H]- and [14C]-curcumin

Curcumin (E,E-1,7-di(4-hydroxy-3-methoxyphenyl)-3-hydroxyhepta-1,3,6-trien-5-one) is an investigational cancer chemopreventive agent. Lithium-bromine exchange of 1-bromo-4-(1-ethoxyethyl)-3-methoxybenzene with butyl lithium, quench with O2HCNMe2 and acidic work-up gave 4-hydroxy-3-methoxybenz-[2H]-aldehyde ([2H]-vanillin) in 27% yield (based on O2HCNMe2). Condensation with pentane-2,4-dione then gave E,E-1,7-di(4-hydroxy-3-methoxyphenyl)-3-hydroxy-1,7-di-[2H]-hepta-1,3,6-trien-5 one ([2H2]-curcumin). Adaptation of the procedures and use of OH14CNMe2 provided [14C]-curcumin (specific radioactivity 12·7 MBq mmol−1) via [14C]-vanillin. Copyright © 2000 John Wiley & Sons, Ltd.