Synthesis and antileishmanial activity of the core structure of cristaxenicin A

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

    Research output: Contribution to journalArticle

    2 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 IC50 value of 2.4 μM.

    Original languageEnglish
    Pages (from-to)4355-4357
    Number of pages3
    JournalBioorganic and Medicinal Chemistry Letters
    Volume26
    Issue number17
    DOIs
    Publication statusPublished - 2016 Sep 1

    Fingerprint

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

    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

    Cite this

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

    In: Bioorganic and Medicinal Chemistry Letters, Vol. 26, No. 17, 01.09.2016, p. 4355-4357.

    Research output: Contribution to journalArticle

    Fumiyama, Hitoshi ; Sadayuki, Tomoko ; Osada, Yasutaka ; Goto, Yasuyuki ; Nakao, Youichi ; Hosokawa, Seijiro. / Synthesis and antileishmanial activity of the core structure of cristaxenicin A. In: Bioorganic and Medicinal Chemistry Letters. 2016 ; Vol. 26, No. 17. pp. 4355-4357.
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    AU - Osada, Yasutaka

    AU - Goto, Yasuyuki

    AU - Nakao, Youichi

    AU - Hosokawa, Seijiro

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