title: Efficient synthesis of (+/-)-parasitenone, a novel inhibitor of NF-kappaB.
abstract: Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-kappaB (NF-kappaB) inhibitor that inhibits DNA binding of NF-kappaB components including p65. To inspect its biological activity of 1, we synthesized parasitenone (3), possessing the common epoxycyclohexenone moiety of 1. Assessment of the inhibitory activity against NF-kappaB indicated that the epoxycyclohexenone moiety is the most essential element for the NF-kappaB inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity.
authors: Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan.
authors: Tsuyoshi
authors: T
authors: Saitoh
authors: Eriko
authors: E
authors: Suzuki
authors: Arisa
authors: A
authors: Takasugi
authors: Rika
authors: R
authors: Obata
authors: Yuichi
authors: Y
authors: Ishikawa
authors: Kazuo
authors: K
authors: Umezawa
authors: Shigeru
authors: S
authors: Nishiyama
mesh_terms: D000818:Animals; D001549:Benzamides / Q000494:pharmacology; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000494:pharmacology*; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D016328:NF-kappa B / Q000037:antagonists & inhibitors* / Q000378:metabolism*; D009569:Nitric Oxide / Q000378:metabolism
chemical_list: D001549:Benzamides; D003512:Cyclohexanones; D004852:Epoxy Compounds; D016328:NF-kappa B; C464444:dehydroxymethylepoxyquinomicin; C461799:parasitenone; D009569:Nitric Oxide