Efficient synthesis of (+/-)-parasitenone, a novel inhibitor of NF-kappaB

Tsuyoshi Saitoh; Eriko Suzuki; Arisa Takasugi; Rika Obata; Yuichi Ishikawa; Kazuo Umezawa; Shigeru Nishiyama

doi:10.1016/j.bmcl.2009.07.120

Efficient synthesis of (+/-)-parasitenone, a novel inhibitor of NF-kappaB

Bioorg Med Chem Lett. 2009 Sep 15;19(18):5383-6. doi: 10.1016/j.bmcl.2009.07.120. Epub 2009 Jul 30.

Authors

Tsuyoshi Saitoh¹, Eriko Suzuki, Arisa Takasugi, Rika Obata, Yuichi Ishikawa, Kazuo Umezawa, Shigeru Nishiyama

Affiliation

¹ Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan.

PMID: 19666224
DOI: 10.1016/j.bmcl.2009.07.120

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Benzamides / pharmacology
Cell Line
Cell Proliferation / drug effects
Cell Survival / drug effects
Cyclohexanones / chemical synthesis*
Cyclohexanones / pharmacology*
Epoxy Compounds / chemical synthesis*
Epoxy Compounds / pharmacology*
Macrophages / drug effects
Mice
NF-kappa B / antagonists & inhibitors*
NF-kappa B / metabolism*
Nitric Oxide / metabolism

Substances

Benzamides
Cyclohexanones
Epoxy Compounds
NF-kappa B
dehydroxymethylepoxyquinomicin
parasitenone
Nitric Oxide