Synthesis and antileishmanial activity of the core structure of cristaxenicin A

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

    研究成果: Article

    3 引用 (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 IC50 value of 2.4 μM.

    元の言語English
    ページ(範囲)4355-4357
    ページ数3
    ジャーナルBioorganic and Medicinal Chemistry Letters
    26
    発行部数17
    DOI
    出版物ステータスPublished - 2016 9 1

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    Aldehydes
    Cycloaddition
    Cycloaddition Reaction
    Ketones
    Inhibitory Concentration 50
    cristaxenicin A
    alkoxyl radical

    ASJC Scopus subject areas

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

    これを引用

    Synthesis and antileishmanial activity of the core structure of cristaxenicin A. / Fumiyama, Hitoshi; Sadayuki, Tomoko; Osada, Yasutaka; Goto, Yasuyuki; Nakao, Youichi; Hosokawa, Seijiro.

    :: Bioorganic and Medicinal Chemistry Letters, 巻 26, 番号 17, 01.09.2016, p. 4355-4357.

    研究成果: Article

    Fumiyama, Hitoshi ; Sadayuki, Tomoko ; Osada, Yasutaka ; Goto, Yasuyuki ; Nakao, Youichi ; Hosokawa, Seijiro. / Synthesis and antileishmanial activity of the core structure of cristaxenicin A. :: Bioorganic and Medicinal Chemistry Letters. 2016 ; 巻 26, 番号 17. pp. 4355-4357.
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    AU - Fumiyama, Hitoshi

    AU - Sadayuki, Tomoko

    AU - Osada, Yasutaka

    AU - Goto, Yasuyuki

    AU - Nakao, Youichi

    AU - Hosokawa, Seijiro

    PY - 2016/9/1

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    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 IC50 value of 2.4 μM.

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