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^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

5 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4355-4357
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	26
Issue number	17
DOIs	https://doi.org/10.1016/j.bmcl.2016.06.061
Publication status	Published - 2016

Keywords

Antileishmanial
Cristaxenicin A
Nine-membered ring
Synthesis
[4+2] cycloaddition

ASJC Scopus subject areas

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

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10.1016/j.bmcl.2016.06.061

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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",

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year = "2016",

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

language = "English",

volume = "26",

pages = "4355--4357",

journal = "Bioorganic and Medicinal Chemistry Letters",

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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

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

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SP - 4355

EP - 4357

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 17

ER -

Synthesis and antileishmanial activity of the core structure of cristaxenicin A

Abstract

Keywords

ASJC Scopus subject areas

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