6533b830fe1ef96bd1297afe

RESEARCH PRODUCT

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

Diana PatriziaGiampietro ViolaGirolamo CirrincioneVirginia SpanòFrancesco Dall'acquaPaola BarrajaDaniela VedaldiAnna CarboneAlessia Salvador

subject

AnnulationPyrano-isoindolesStereochemistryChemistry PharmaceuticalClinical BiochemistryPharmaceutical ScienceApoptosisIsoindolesRing (chemistry)BiochemistryChemical synthesisInhibitory Concentration 50Jurkat CellsStructure-Activity Relationshipchemistry.chemical_compoundAngelicinCell Line TumorFurocoumarinsDrug DiscoveryHumansMoietyMolecular BiologyPyransMolecular StructurePyrano-isoindoleChemistryPhotochemotherapeutic activityOrganic ChemistryPyrano-isoindoles; Angelicin heteroanalogues; Photochemotherapeutic activity; ApoptosisSettore CHIM/08 - Chimica FarmaceuticaAngelicin heteroanaloguesOxygenModels ChemicalPyranDrug DesignBenzyl groupMolecular MedicineK562 CellsIsoindoleAngelicin heteroanalogue

description

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.

yearjournalcountryeditionlanguage
2009-01-01Bioorganic & Medicinal Chemistry Letters
https://doi.org/10.1016/j.bmcl.2009.01.096