Author/Authors :
Takashi Kitayama، نويسنده , , Maki Nakahira، نويسنده , , Kae Yamasaki، نويسنده , , Hiromi Inoue، نويسنده , , Chika Imada، نويسنده , , Yuji Yonekura، نويسنده , , Masataka Awata، نويسنده , , Hikaru Takaya، نويسنده , , Yasushi Kawai، نويسنده , , Kohta Ohnishi، نويسنده , , Akira Murakami، نويسنده ,
Abstract :
Zerumbone 1, having powerful latent reactivity and containing two conjugated double bonds and a double conjugated carbonyl group is the major component of the essential oil of wild ginger, Zingiber zerumbet Smith. The conjugation system plays an important role in the expression of biological activity. N-Bromosuccinimide (NBS) reaction of 1 gave high reactive intermediate 2 with an exo-methylene group, which was obtained from 1 quantitatively. Treatment of 2 with nucleophiles gave various zerumbone-pendant derivatives, including C–H, C–O, C–N, and C–C bond formation, maintaining the conjugation system through SN2′-type reaction. Almost all zerumbone-pendant derivatives showed a good value of IC50 against the suppressive effect of NO generation. Among them, amine derivative 5, binding with 2 mol of zerumbone, showed the strongest activity (IC50: 0.24 μM).
