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

Ifat Shah; Michael D. Threadgill

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

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

University of Bath

Allbwn ymchwil: Cyfraniad at gyfnodolyn › Erthygl › adolygiad gan gymheiriaid

5 Dyfyniadau (Scopus)

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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.

Iaith wreiddiol	Saesneg
Tudalennau (o-i)	883-889
Nifer y tudalennau	7
Cyfnodolyn	Journal of Labelled Compounds and Radiopharmaceuticals
Cyfrol	43
Rhif cyhoeddi	9
Dynodwyr Gwrthrych Digidol (DOIs)	https://doi.org/10.1002/1099-1344(200008)43:9<883::AID-JLCR372>3.0.CO;2-4
Statws	Cyhoeddwyd - Awst 2000
Cyhoeddwyd yn allanol	Ie

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

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@article{fb9ced0aeaf342b787bac87549fe9416,

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

abstract = "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.",

keywords = "C, Curcumin, Dimethylformamide, H, Lithiation, Vanillin",

author = "Ifat Shah and Threadgill, \{Michael D.\}",

year = "2000",

month = aug,

doi = "10.1002/1099-1344(200008)43:9<883::AID-JLCR372>3.0.CO;2-4",

language = "English",

volume = "43",

pages = "883--889",

journal = "Journal of Labelled Compounds and Radiopharmaceuticals",

issn = "0362-4803",

publisher = "Wiley",

number = "9",

}

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 - https://www.scopus.com/pages/publications/0033925291

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 -

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

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