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

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

Research output: Contribution to journal › Article

13 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 languageEnglish
Pages (from-to)5383-5386
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number18
DOIs
Publication statusPublished - 2009 Sep 15

Fingerprint

Salicylic Acid
Bioactivity
DNA
parasitenone
dehydroxymethylepoxyquinomicin

Keywords

  • Anodic oxidation
  • DHMEQ
  • Epoxycyclohexenone
  • NF-κB inhibitor
  • Parasitenone

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry
  • Medicine(all)

Cite this

Saitoh, T., Suzuki, E., Takasugi, A., Obata, R., Ishikawa, Y., Umezawa, K., & Nishiyama, S. (2009). Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB. Bioorganic and Medicinal Chemistry Letters, 19(18), 5383-5386. https://doi.org/10.1016/j.bmcl.2009.07.120

Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB. / Saitoh, Tsuyoshi; Suzuki, Eriko; Takasugi, Arisa; Obata, Rika; Ishikawa, Yuichi; Umezawa, Kazuo; Nishiyama, Shigeru.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 19, No. 18, 15.09.2009, p. 5383-5386.

Research output: Contribution to journal › Article

Saitoh, T, Suzuki, E, Takasugi, A, Obata, R, Ishikawa, Y, Umezawa, K & Nishiyama, S 2009, 'Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB', Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 18, pp. 5383-5386. https://doi.org/10.1016/j.bmcl.2009.07.120
Saitoh T, Suzuki E, Takasugi A, Obata R, Ishikawa Y, Umezawa K et al. Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB. Bioorganic and Medicinal Chemistry Letters. 2009 Sep 15;19(18):5383-5386. https://doi.org/10.1016/j.bmcl.2009.07.120
Saitoh, Tsuyoshi ; Suzuki, Eriko ; Takasugi, Arisa ; Obata, Rika ; Ishikawa, Yuichi ; Umezawa, Kazuo ; Nishiyama, Shigeru. / Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB. In: Bioorganic and Medicinal Chemistry Letters. 2009 ; Vol. 19, No. 18. pp. 5383-5386.
@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",
year = "2009",
month = "9",
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

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

VL - 19

SP - 5383

EP - 5386

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 18

ER -

Access to Document