Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB

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-κB

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

人文社会学科

研究成果: Article › 査読

17 被引用数 (Scopus)

抄録

Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-κB (NF-κB) inhibitor that inhibits DNA binding of NF-κB 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-κB indicated that the epoxycyclohexenone moiety is the most essential element for the NF-κB inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity.

本文言語	English
ページ（範囲）	5383-5386
ページ数	4
ジャーナル	Bioorganic and Medicinal Chemistry Letters
巻	19
号	18
DOI	https://doi.org/10.1016/j.bmcl.2009.07.120
出版ステータス	Published - 2009 9月 15

ASJC Scopus subject areas

生化学
分子医療
分子生物学
薬科学
創薬
臨床生化学
有機化学

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10.1016/j.bmcl.2009.07.120

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title = "Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB",

abstract = "Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-κB (NF-κB) inhibitor that inhibits DNA binding of NF-κB 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-κB indicated that the epoxycyclohexenone moiety is the most essential element for the NF-κB inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity.",

keywords = "Anodic oxidation, DHMEQ, Epoxycyclohexenone, NF-κB inhibitor, Parasitenone",

author = "Tsuyoshi Saitoh and Eriko Suzuki and Arisa Takasugi and Rika Obata and Yuichi Ishikawa and Kazuo Umezawa and Shigeru Nishiyama",

note = "Funding Information: This work was supported by High-Tech Research Center Project for subsidy from MEXT, 2006–2011, Japan. T.S. was indebted to Global COE Program {\textquoteleft}Center for Human Metabolomic Systems Biology{\textquoteright} from MEXT.",

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doi = "10.1016/j.bmcl.2009.07.120",

language = "English",

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T1 - Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB

AU - Saitoh, Tsuyoshi

AU - Suzuki, Eriko

AU - Takasugi, Arisa

AU - Obata, Rika

AU - Ishikawa, Yuichi

AU - Umezawa, Kazuo

AU - Nishiyama, Shigeru

N1 - Funding Information: This work was supported by High-Tech Research Center Project for subsidy from MEXT, 2006–2011, Japan. T.S. was indebted to Global COE Program ‘Center for Human Metabolomic Systems Biology’ from MEXT.

PY - 2009/9/15

Y1 - 2009/9/15

N2 - Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-κB (NF-κB) inhibitor that inhibits DNA binding of NF-κB 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-κB indicated that the epoxycyclohexenone moiety is the most essential element for the NF-κB inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity.

AB - Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-κB (NF-κB) inhibitor that inhibits DNA binding of NF-κB 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-κB indicated that the epoxycyclohexenone moiety is the most essential element for the NF-κB inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity.

KW - Anodic oxidation

KW - DHMEQ

KW - Epoxycyclohexenone

KW - NF-κB inhibitor

KW - Parasitenone

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EP - 5386

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

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ER -

Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB

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