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

Department of Humanities and Social Sciences

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5383-5386
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	18
DOIs	https://doi.org/10.1016/j.bmcl.2009.07.120
Publication status	Published - 2009 Sep 15

Keywords

Anodic oxidation
DHMEQ
Epoxycyclohexenone
NF-κB inhibitor
Parasitenone

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Access to Document

10.1016/j.bmcl.2009.07.120

Cite this

@article{dfdae8527c144c5d8e8276b53ee3cd6a,

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.",

year = "2009",

month = sep,

day = "15",

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

language = "English",

volume = "19",

pages = "5383--5386",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "18",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=68949108026&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=68949108026&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2009.07.120

DO - 10.1016/j.bmcl.2009.07.120

M3 - Article

C2 - 19666224

AN - SCOPUS:68949108026

VL - 19

SP - 5383

EP - 5386

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 18

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this