title: Pyrano[2,3-e]isoindol-2-ones, new angelicin heteroanalogues.
abstract: 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 IC(50) in the micromolar range. Cell cytotoxicity involves apoptosis, alteration of cell cycle profile and membrane photodamage.
authors.affiliation: Dipartimento Farmacochimico, Tossicologico e Biologico, Università degli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy.
authors.forename: Paola
authors.initials: P
authors.lastname: Barraja
authors.forename: Virginia
authors.initials: V
authors.lastname: Spanò
authors.forename: Diana
authors.initials: D
authors.lastname: Patrizia
authors.forename: Anna
authors.initials: A
authors.lastname: Carbone
authors.forename: Girolamo
authors.initials: G
authors.lastname: Cirrincione
authors.forename: Daniela
authors.initials: D
authors.lastname: Vedaldi
authors.forename: Alessia
authors.initials: A
authors.lastname: Salvador
authors.forename: Giampietro
authors.initials: G
authors.lastname: Viola
authors.forename: Francesco
authors.initials: F
authors.lastname: Dall'acqua
mesh_terms: D017209:Apoptosis; D045744:Cell Line, Tumor; D002626:Chemistry, Pharmaceutical / Q000379:methods; D015195:Drug Design; D011564:Furocoumarins / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D054833:Isoindoles / Q000494:pharmacology*; D019169:Jurkat Cells; D020014:K562 Cells; D008956:Models, Chemical; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D011714:Pyrans / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D011564:Furocoumarins; D054833:Isoindoles; D011714:Pyrans; C011659:angelicin; D010100:Oxygen