title: Structure-Activity Relationships of the Antitumor C5-Curcuminoid GO-Y030.
abstract: 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.
authors: Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan. a-kohyama@dc.tohoku.ac.jp.
authors: Aki
authors: A
authors: Kohyama
authors: Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan. yamakoshi@phar.nagoya-cu.ac.jp.
authors: Hiroyuki
authors: H
authors: Yamakoshi
authors: Department of Clinical Oncology, Faculty of Medicine, Akita University, Akita 010-8643, Japan. hongoh23@gmail.com.
authors: Shoko
authors: S
authors: Hongo
authors: Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan. nkanoh@m.tohoku.ac.jp.
authors: Naoki
authors: N
authors: Kanoh
authors: Department of Clinical Oncology, Faculty of Medicine, Akita University, Akita 010-8643, Japan. hiroyuki@med.akita-u.ac.jp.
authors: Hiroyuki
authors: H
authors: Shibata
authors: Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan. y-iwabuchi@m.tohoku.ac.jp.
authors: Yoshiharu
authors: Y
authors: Iwabuchi
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D003474:Curcumin / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004583:Electrons; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011522:Protons; D013329:Structure-Activity Relationship
chemical_list: C541015:1,5-bis(3,5-bis(methoxymethoxy)phenyl)penta-1,4-dien-3-one; D000970:Antineoplastic Agents; D001555:Benzene Derivatives; D007659:Ketones; D011522:Protons; D003474:Curcumin
keywords: Michael reaction; antitumor; curcumin; structure-activity relationship