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Molecules 2015, 20(8), 15374-15391;

Structure-Activity Relationships of the Antitumor C5-Curcuminoid GO-Y030

Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan
Department of Clinical Oncology, Faculty of Medicine, Akita University, Akita 010-8643, Japan
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 24 July 2015 / Revised: 19 August 2015 / Accepted: 19 August 2015 / Published: 24 August 2015
(This article belongs to the Section Medicinal Chemistry)
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1,5-Bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadiene-3-one (2) was isolated from Curcuma domestica as a curcumin (1)-related compound, which we named C5-curcumin. Intrigued by the potent antitumor activity of C5-curcumin (2)-related 1,5-bisaryl-1,4-pentadiene-3-ones [bis(arylmethylidene)acetones, termed C5-curcuminoids], we previously conducted a structure–activity relationship study of C5-curcuminoids and showed that highly active GO-Y030 [1,5-bis(3,5-bis(methoxymethoxy)phenyl)-1,4-pentadiene-3-one (4)] is the most promising antitumor compound. In this study, a panel of C5-curcuminoids based on GO-Y030, consisting of 30 new and 10 known compounds, was synthesized to elucidate in detail which moiety of GO-Y030 is significant for antitumor activity. The results confirmed that both the cross-conjugated dienone moiety and the 3,5-bis(methoxymethoxy) substituent are important for the antitumor activity. View Full-Text
Keywords: curcumin; antitumor; Michael reaction; structure-activity relationship curcumin; antitumor; Michael reaction; structure-activity relationship

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kohyama, A.; Yamakoshi, H.; Hongo, S.; Kanoh, N.; Shibata, H.; Iwabuchi, Y. Structure-Activity Relationships of the Antitumor C5-Curcuminoid GO-Y030. Molecules 2015, 20, 15374-15391.

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