Efficient synthesis of (+/-)-parasitenone, a novel inhibitor of NF-[kappa]B

Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-[kappa]B (NF-[kappa]B) inhibitor that inhibits DNA binding of NF-[kappa]B components including p65. To inspect its biological activity of 1, we synthesized parasitenone ( 3), possessing the common epoxycyclohexenone moiety of 1. Ass...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2009-09, Vol.19 (18), p.5383-5386
Main Authors: Saitoh, Tsuyoshi, Suzuki, Eriko, Takasugi, Arisa, Obata, Rika, Ishikawa, Yuichi, Umezawa, Kazuo, Nishiyama, Shigeru
Format: Article
Language:English
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Summary:Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-[kappa]B (NF-[kappa]B) inhibitor that inhibits DNA binding of NF-[kappa]B 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-[kappa]B indicated that the epoxycyclohexenone moiety is the most essential element for the NF-[kappa]B inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity.
ISSN:0960-894X
DOI:10.1016/j.bmcl.2009.07.120