Labelled compounds of interest as antitumour agents - VII(I) [2H]- and [14C]-Curcumin

Article abstract of DOI:10.1002/1099-1344(200008)43:9<883::AID-JLCR372>3.0.CO;2-4

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.