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

Valente Sergio | Zendy; Xu Zhanjie | Zendy; Bana Emilie | Zendy; Zwergel Clemens | Zendy; Mai Antonello | Zendy; Jacob Claus | Zendy; Meiser Peter | Zendy; Bagrel Denyse | Zendy; Silva Artur M. S. | Zendy; Kirsch Gilbert | Zendy

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

Author(s) -

Valente Sergio,

Xu Zhanjie,

Bana Emilie,

Zwergel Clemens,

Mai Antonello,

Jacob Claus,

Meiser Peter,

Bagrel Denyse,

Silva Artur M. S.,

Kirsch Gilbert

Publication year - 2013

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201201736

Subject(s) - chemistry , cycloaddition , reactivity (psychology) , coumarin , diene , medicinal chemistry , diels–alder reaction , organic chemistry , catalysis , medicine , natural rubber , alternative medicine , pathology

The reactivity of 4‐(1‐butoxyvinyl)‐2 H ‐chromen‐2‐one ( 1 ) and ( E )‐4‐(2‐butoxyvinyl)‐2 H ‐chromen‐2‐one ( 2 ) as diene in thermal Diels–Alder cycloaddition reactions with several electron‐poor dienophiles is reported. Among several dienophiles used in this study 1,4‐benzoquinone afforded cycloadducts 11‐butoxy‐1 H ‐naphtho[1,2‐ c ]chromene‐1,4,5‐trione ( 3e ) and 1 H ‐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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