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

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.

A versatile and convenient pathway for the synthesis of pyrano[2,3-e]isoindol-2-one derivatives and their photochemotherapeutic activity are reported.Figure optionsDownload as PowerPoint slide