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J-GLOBAL ID：201402234079225269   Reference number：14A0405058

Synthesis and Evaluation of a Cyclopropane Derivative of DHMEQ

DHMEQのシクロプロパン誘導体の合成および評価

Author (6)： YASUI Eiko (Dep. of Applied Chemistry, Kogakuin Univ.) ,  TAKAYAMA Kan (Dep. of Applied Chemistry, Kogakuin Univ.) ,  NAKAGO Takahiro (Dep. of Applied Chemistry, Kogakuin Univ.) ,  TAKEDA Nobuyuki (Dep. of Applied Chemistry, Kogakuin Univ.) ,  IMAMURA Yasutada (Dep. of Applied Chemistry, Kogakuin Univ.) ,  NAGUMO Shinji (Dep. of Applied Chemistry, Kogakuin Univ.)
Material： Chemical and Pharmaceutical Bulletin  (Chemical & Pharmaceutical Bulletin)
Volume： 62  Issue： 3  Page： 304-307 (J-STAGE)  Publication year： 2014 
JST Material Number： G0504A  ISSN： 0009-2363  CODEN： CPBTAL  Document type： Article
Article type： 短報  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： asymmetric synthesis ,...
Semi thesaurus term： NF kappa B inhibitor ,...

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JST classification (2)： Other condensed bicyclic carbocyclic compounds containing 6-membered ring  (CF06040Z) ,  Basic research of antitumor(=antineoplastic)drugs  (GW16010A)

Substance index (2)： (-)-DHMEQ ,  (1β,6β)-4-(2-Hydroxybenzoylamino)-5α-hydroxybicyclo[4.1.0]hepta-3-ene-2-one

Reference (9)：

• 1) Olivier S., Robe P., Bours V., Biochem. Pharmacol., 72, 1054-1068 (2006).
• 2) Matsumoto N., Ariga A., To-e S., Nakamura H., Agata N., Hirano S., Inoue J., Umezawa K., Bioorg. Med. Chem. Lett., 10, 865-869 (2000).
• 3) Yamamoto M., Horie R., Takeiri M., Kozawa I., Umezawa K., J. Med. Chem., 51, 5780-5788 (2008).
• 4) Compound 3a, a derivative of DHMEQ with the same stereochemistry, scarcely inhibited NF-κB activation, but it weakly binds to p65. On the other hand, compound 3b, a derivative of DHMEQ with the opposite stereochemistry, inhibited NF-κB activation dose-dependently, but it does not bind to p65 (refer to ref. 5). Compound 8 was synthesized to examine structure-activity correlation of cyclopropane derivatives. The synthesis of epimer of compound 8 (cyclopropane ring and hydroxyl group are substituted as anti) and their inhibitory activities against NF-κB would be reported in the next paper.
• 5) Saitoh T., Shimada C., Takeiri M., Shiino M., Ohba S., Obata R., Ishikawa Y., Umezawa K., Nishiyama S., Bioorg. Med. Chem. Lett., 20, 5638-5642 (2010).

Terms in the title (3)： DHMEQ ,  シクロプロパン誘導体 ,  評価