TY - JOUR
T1 - Labelled compounds of interest as antitumour agents-VII1. [2H]- and [14C]-curcumin
AU - Shah, Ifat
AU - Threadgill, Michael D.
PY - 2000/8
Y1 - 2000/8
N2 - 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.
AB - 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.
KW - C
KW - Curcumin
KW - Dimethylformamide
KW - H
KW - Lithiation
KW - Vanillin
UR - http://hdl.handle.net/2160/43502
UR - http://www.scopus.com/inward/record.url?scp=0033925291&partnerID=8YFLogxK
U2 - 10.1002/1099-1344(200008)43:9<883::AID-JLCR372>3.0.CO;2-4
DO - 10.1002/1099-1344(200008)43:9<883::AID-JLCR372>3.0.CO;2-4
M3 - Article
SN - 0362-4803
VL - 43
SP - 883
EP - 889
JO - Journal of Labelled Compounds and Radiopharmaceuticals
JF - Journal of Labelled Compounds and Radiopharmaceuticals
IS - 9
ER -
