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Reactivity of 4-Vinyl-2H-1-benzopyran-2-ones in Diels-Alder Cycloaddition Reactions: Access to Coumarin-Based Polycycles with Cdc25 Phosphatase-Inhibiting Activity

Abstract : The reactivity of 4-(1-butoxyvinyl)-2H-chromen-2-one (1) and (E)-4-(2-butoxyvinyl)-2H-chromen-2-one (2) as diene in thermal DielsAlder cycloaddition reactions with several electron-poor dienophiles is reported. Among several dienophiles used in this study 1,4-benzoquinone afforded cycloadducts 11-butoxy-1H-naphtho[1,2-c]chromene-1,4,5-trione (3e) and 1H-naphtho[1,2-c]chromene-1,4,5-trione (4g) that showed Cdc25 phosphatase-inhibition activity at low micromolar values, with both compounds more effective against Cdc25 A and Cdc25 C isoforms.
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Submitted on : Wednesday, March 22, 2017 - 4:40:21 PM
Last modification on : Friday, February 26, 2021 - 3:24:02 PM

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Sergio Valente, Zhanjie Xu, Emilie Bana, Clemens Zwergel, Antonello Mai, et al.. Reactivity of 4-Vinyl-2H-1-benzopyran-2-ones in Diels-Alder Cycloaddition Reactions: Access to Coumarin-Based Polycycles with Cdc25 Phosphatase-Inhibiting Activity. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2013, pp.2869-2877. ⟨10.1002/ejoc.201201736⟩. ⟨hal-01494085⟩

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