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Pyrano[2,3-e]isoindol-2-ones, new angelicin heteroanalogues

  • Autori: Barraja, P.; Spano', V.; Diana, P.; Carbone, A.; Cirrincione, G.; Vedaldi, D.; Salvador, A.; Viola, G.; Dall'Acqua, F.
  • Anno di pubblicazione: 2009
  • Tipologia: Articolo in rivista (Articolo in rivista)
  • Parole Chiave: Pyrano-isoindoles; Angelicin heteroanalogues; Photochemotherapeutic activity; Apoptosis
  • OA Link:


A convenient synthesis of the pyrano[2,3-e ]isoindol-2-one ring system, an heteroanalogue of angelicin, is reported. Our synthetic approach consists of the annelation of the pyran ring on the isoindole moiety using 5-dialkylamino- or 5-hydroxymethylene intermediates as building blocks. The photoantiproliferative activity of the new derivatives was studied. Some of them bearing the benzyl group at the 8 position were active with IC50 in the micromolar range. Cell cytotoxicity involves apoptosis, alteration of cell cycle profile and membrane photodamage.