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Pyrrolo[3′,2′:6,7]cyclohepta[1,2-b]pyridines with potent photo-antiproliferative activity

  • Authors: Spanò, V.; Giallombardo, D.; Cilibrasi, V.; Parrino, B.; Carbone, A.; Montalbano, A.; Frasson, I.; Salvador, A.; Richter, S.; Doria, F.; Freccero, M.; Cascioferro, S.; Diana, P.; Cirrincione, G.; Barraja, P.
  • Publication year: 2017
  • Type: Articolo in rivista (Articolo in rivista)
  • Key words: Photo-antiproliferative activity; Photosensitizing agents; Phototoxicity; Pyrrolo[3′,2′:6,7]cyclohepta[1,2-b]pyridine-9(1H)-ones; Reactive oxygen species; Pharmacology; Drug Discovery3003 Pharmaceutical Science; Organic Chemistry
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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 EC50values reaching the submicromolar level. The mechanism of action was evaluated.