Synthesis and antileishmanial activity of the core structure of cristaxenicin A

Hitoshi Fumiyama; Tomoko Sadayuki; Yasutaka Osada; Yasuyuki Goto; Yoichi Nakao; Seijiro Hosokawa

doi:10.1016/j.bmcl.2016.06.061

Synthesis and antileishmanial activity of the core structure of cristaxenicin A

Hitoshi Fumiyama, Tomoko Sadayuki, Yasutaka Osada, Yasuyuki Goto, Yoichi Nakao, Seijiro Hosokawa

先進理工学部

研究成果: Article › 査読

3 被引用数 (Scopus)

抄録

The core structure of cristaxenicin A having trans-fused dihydropyran and nine membered ring has been synthesized and evaluated the antileishmanial activity. The dihydropyran ring was synthesized by [4+2] cycloaddition reaction between an unsaturated aldehyde and a β-alkoxy-α,β-unsaturated ketone. The nine membered ring possessing α,β-unsaturated aldehyde was constructed by the intramolecular NHK reaction followed by the Mitsunobu rearrangement. The racemic core structure of cristaxenicin A was evaluated the anti-leishmanial activity with an IC₅₀value of 2.4 μM.

本文言語	English
ページ（範囲）	4355-4357
ページ数	3
ジャーナル	Bioorganic and Medicinal Chemistry Letters
巻	26
号	17
DOI	https://doi.org/10.1016/j.bmcl.2016.06.061
出版ステータス	Published - 2016

ASJC Scopus subject areas

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

文献へのアクセス

10.1016/j.bmcl.2016.06.061

フィンガープリント「Synthesis and antileishmanial activity of the core structure of cristaxenicin A」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

@article{ca26be2434e94e4b90771744f1f2fa74,

title = "Synthesis and antileishmanial activity of the core structure of cristaxenicin A",

abstract = "The core structure of cristaxenicin A having trans-fused dihydropyran and nine membered ring has been synthesized and evaluated the antileishmanial activity. The dihydropyran ring was synthesized by [4+2] cycloaddition reaction between an unsaturated aldehyde and a β-alkoxy-α,β-unsaturated ketone. The nine membered ring possessing α,β-unsaturated aldehyde was constructed by the intramolecular NHK reaction followed by the Mitsunobu rearrangement. The racemic core structure of cristaxenicin A was evaluated the anti-leishmanial activity with an IC50value of 2.4 μM.",

keywords = "Antileishmanial, Cristaxenicin A, Nine-membered ring, Synthesis, [4+2] cycloaddition",

author = "Hitoshi Fumiyama and Tomoko Sadayuki and Yasutaka Osada and Yasuyuki Goto and Yoichi Nakao and Seijiro Hosokawa",

note = "Funding Information: Authors are grateful for financial support to The Kurata Memorial Hitachi Science and Technology Foundation and The Naito Foundation . This Letter is a part of the outcome of research performed under a Waseda University Grant for Special Research Projects (Project number: 2008A-059). ",

year = "2016",

doi = "10.1016/j.bmcl.2016.06.061",

language = "English",

volume = "26",

pages = "4355--4357",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "17",

}

TY - JOUR

T1 - Synthesis and antileishmanial activity of the core structure of cristaxenicin A

AU - Fumiyama, Hitoshi

AU - Sadayuki, Tomoko

AU - Osada, Yasutaka

AU - Goto, Yasuyuki

AU - Nakao, Yoichi

AU - Hosokawa, Seijiro

N1 - Funding Information: Authors are grateful for financial support to The Kurata Memorial Hitachi Science and Technology Foundation and The Naito Foundation . This Letter is a part of the outcome of research performed under a Waseda University Grant for Special Research Projects (Project number: 2008A-059).

PY - 2016

Y1 - 2016

N2 - The core structure of cristaxenicin A having trans-fused dihydropyran and nine membered ring has been synthesized and evaluated the antileishmanial activity. The dihydropyran ring was synthesized by [4+2] cycloaddition reaction between an unsaturated aldehyde and a β-alkoxy-α,β-unsaturated ketone. The nine membered ring possessing α,β-unsaturated aldehyde was constructed by the intramolecular NHK reaction followed by the Mitsunobu rearrangement. The racemic core structure of cristaxenicin A was evaluated the anti-leishmanial activity with an IC50value of 2.4 μM.

AB - The core structure of cristaxenicin A having trans-fused dihydropyran and nine membered ring has been synthesized and evaluated the antileishmanial activity. The dihydropyran ring was synthesized by [4+2] cycloaddition reaction between an unsaturated aldehyde and a β-alkoxy-α,β-unsaturated ketone. The nine membered ring possessing α,β-unsaturated aldehyde was constructed by the intramolecular NHK reaction followed by the Mitsunobu rearrangement. The racemic core structure of cristaxenicin A was evaluated the anti-leishmanial activity with an IC50value of 2.4 μM.

KW - Antileishmanial

KW - Cristaxenicin A

KW - Nine-membered ring

KW - Synthesis

KW - [4+2] cycloaddition

UR - http://www.scopus.com/inward/record.url?scp=84981333797&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84981333797&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2016.06.061

DO - 10.1016/j.bmcl.2016.06.061

M3 - Article

C2 - 27476143

AN - SCOPUS:84981333797

VL - 26

SP - 4355

EP - 4357

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 17

ER -