Details

Autor(en) / Beteiligte

• Shen, Xiurui
• Yang, Xiaomei
• Zhu, Ying
• Liu, Xihuan
• Wen, Hongliang

Titel

Synthesis of [18O2]-curcumin

Ist Teil von

• Journal of labelled compounds & radiopharmaceuticals, 2014-09, Vol.57 (11), p.658-659

Ort / Verlag

England: Blackwell Publishing Ltd

Erscheinungsjahr

2014

Link zum Volltext

Quelle

Wiley Online Library Journals Frontfile Complete

Beschreibungen/Notizen

• Curcumin, a pigment isolated from rhizomes of Curcuma longa, is a potent cancer chemopreventive and chemotherapeutic agent and is now evaluated in phase III human clinical trials. This report describes an efficient synthesis of [18O2]‐curcumin. [18O2]‐Curcumin was prepared in three steps from 1‐iodo‐2‐methoxy‐4‐methylbenzene in an overall yield of 53%. This report presents an efficient synthesis of [18O2]‐curcumin. Hydroxylation of 1‐iodo‐2‐methoxy‐4‐methylbenzene with K18OH in a mixed solvent system (t‐BuOH‐dimethyl sulphoxide‐H218O) catalyzed with CuI/8‐hydroxyquinoline gave [18O]‐2‐methoxy‐4‐methylphenol in 87% yield. The oxidation of the methyl group at C‐4 of [18O]‐2‐methoxy‐4‐methylphenol with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone in CH2Cl2 at room temperature gave [18O]‐vanillin in 85% yield. Finally, condensation with pentane‐2,4‐dione and [18O2]‐curcumin was obtained.