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Labelled compounds of interest as antitumour agents‐VII 1 . [ 2 H]‐ and [ 14 C]‐curcumin
Author(s) -
Parveen Ifat,
Threadgill Michael D.
Publication year - 2000
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/1099-1344(200008)43:9<883::aid-jlcr372>3.0.co;2-4
Subject(s) - chemistry , curcumin , vanillin , yield (engineering) , lithium (medication) , pentane , bromine , organic chemistry , medicinal chemistry , stereochemistry , biochemistry , metallurgy , endocrinology , medicine , materials science
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 O 2 HCNMe 2 and acidic work‐up gave 4‐hydroxy‐3‐methoxybenz‐[ 2 H]‐aldehyde ([ 2 H]‐vanillin) in 27% yield (based on O 2 HCNMe 2 ). Condensation with pentane‐2,4‐dione then gave E , E ‐1,7‐di(4‐hydroxy‐3‐methoxyphenyl)‐3‐hydroxy‐1,7‐di‐[ 2 H]‐hepta‐1,3,6‐trien‐5 one ([ 2 H 2 ]‐curcumin). Adaptation of the procedures and use of OH 14 CNMe 2 provided [ 14 C]‐curcumin (specific radioactivity 12·7 MBq mmol −1 ) via [ 14 C]‐vanillin. Copyright © 2000 John Wiley & Sons, Ltd.