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

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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 EC50values reaching the submicromolar level. The mechanism of action was evaluated.
Original languageEnglish
Pages (from-to)300-318
Number of pages19
JournalEuropean Journal of Medicinal Chemistry
Volume128
Publication statusPublished - 2017

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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