Biomimetic Photocycloaddition of 3-Hydroxyflavones: Synthesis and Evaluation of Rocaglate Derivatives as Inhibitors of Eukaryotic Translation

Authors

  • Stéphane P. Roche Dr.,

    1. Department of Chemistry, Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston MA, 02215 (USA), Fax: (+1) 617-358-2847
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  • Regina Cencic Dr.,

    1. McGill University, Department of Biochemistry and The Rosalind and Morris Goodman Cancer Research Centre, Room 810, 3655 Drummond St., Montreal, QC, H3G 1Y6 (Canada), Fax: (+1) 514-398-7384
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  • Jerry Pelletier Prof. Dr.,

    1. McGill University, Department of Biochemistry and The Rosalind and Morris Goodman Cancer Research Centre, Room 810, 3655 Drummond St., Montreal, QC, H3G 1Y6 (Canada), Fax: (+1) 514-398-7384
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  • John A. Porco Jr. Prof. Dr.

    1. Department of Chemistry, Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston MA, 02215 (USA), Fax: (+1) 617-358-2847
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  • Financial support from the National Institutes of Health (R01 GM073855) is gratefully acknowledged. We thank Professors R. Johnson (UNH), F. D. Lewis (Northwestern University), and Dr. Baudouin Gerard (Broad Institute) for extremely helpful and stimulating discussions.

Abstract

original image

Durch Licht geschaffen: Die Titelreaktion wurde zur Synthese einer Reihe von Rocaglat-Derivaten genutzt. Mechanistischen Studien zufolge könnten Donor-Akzeptor-Wechselwirkungen und Triplettdiradikal-artige Zustände am photochemisch angeregten Zustand beteiligt sein. Einige neue Rocaglat-Derivate reichen in ihrer Wirksamkeit an das Tumortherapeutikum Silvestrol heran.

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