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  • Title: Pyrrolo[3',2':6,7]cyclohepta[1,2-b]pyridines with potent photo-antiproliferative activity.
    Author: Spanò V, Giallombardo D, Cilibrasi V, Parrino B, Carbone A, Montalbano A, Frasson I, Salvador A, Richter SN, Doria F, Freccero M, Cascioferro S, Diana P, Cirrincione G, Barraja P.
    Journal: Eur J Med Chem; 2017 Mar 10; 128():300-318. PubMed ID: 28213283.
    Abstract:
    Pyrrolo[3',2':6,7]cyclohepta[1,2-b]pyridines were synthesized as a new class of tricyclic system in which the pyridine ring is annelated to a cycloheptapyrrole scaffold, with the aim of obtaining new photosensitizing agents with improved antiproliferative activity and lower undesired toxic effects. A versatile synthetic pathway was approached, which allowed the isolation of derivatives of the title ring system with a good substitution pattern on the pyrrole moiety. Photobiological studies revealed that the majority of the new compounds showed a potent cytotoxic effect upon photoactivation with light of the proper wavelength, especially when decorated with a 2-ethoxycabonyl group and a N-benzyl substituted moiety, with EC50 values reaching the submicromolar level. The mechanism of action was evaluated.
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