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RESEARCH FRONT
Contents Vol 68(2)

Synthesis and Tautomerism of Curcumin Derivatives and Related Compounds

Hiroyasu Taguchi A D , Daijiro Yanagisawa A , Shigehiro Morikawa B , Koichi Hirao C , Nobuaki Shirai C and Ikuo Tooyama A
+ Author Affiliations
- Author Affiliations

A Molecular Neuroscience Research Center, Shiga University of Medical Science, Seta Tsukinowa-cho, Otsu 520-2192, Japan.

B Biomedical MR Science Center, Shiga University of Medical Science, Seta Tsukinowa-cho, Otsu 520-2192, Japan.

C Northeastern Industrial Research Center of Shiga Prefecture, 27-39 Mitsuya Motomachi, Nagahama 526-0024, Japan.

D Corresponding author. Email: taguti@belle.shiga-med.ac.jp

Australian Journal of Chemistry 68(2) 224-229 https://doi.org/10.1071/CH14464
Submitted: 22 July 2014  Accepted: 1 August 2014   Published: 27 October 2014

Abstract

1,7-Bis(4′-hydroxy-3′-trifluoromethoxyphenyl)-1,6-heptadiene-3,5-dione (2a), related to curcumin, and thirteen 4-substituted derivatives were prepared and their keto/enol ratio in DMSO[D6] was determined by 19F NMR because the enolic form of these related curcumins had been shown to bind to amyloid plaques in the Alzheimer brain. The parent compound and the 4-ethoxycarbonyl derivative were almost 100 % in the enolic form that contains a conjugated hepta-1,4,6-trien-3-on-5-ol backbone. Enolisation decreased to varying amounts in the derivatives that had 4-substituted alkyl groups. Attempts to prepare the 4-hydroxypropyl derivative by hydrolysis of O-methoxymethyl 2m or O-tetrahydropyranyloxy 2n protected derivatives led to cyclised products. A related pyrimidine compound 6b that mimicked a fixed enol form was also prepared.


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