Synthesis and electrophilic substitution of pyrido[2,3,4-kl]-acridines

Avi Koller, Amira Rudi, Marta Garcia Gravalos, Yoel Kashman*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Several new pyrido[2,3,4-kl]acridines were synthesized by reacting naphthoquinone, juglone or cyclohexan-1,3-dione with β,β'- diaminoketones in a biomimetic reaction. The structure of all new compounds was elucidated by NMR and MS spectroscopy. Electrophilic substitution, mainly nitration, of the various compounds was undertaken and the substitution positions determined. A series of derivatives was prepared and their cytotoxicity towards P-388 mouse lymphoma cells analysed. The most cytotoxic derivatives were found to have IC50's of 0.05 and 0.1 ug/ml.

Original languageEnglish
Pages (from-to)300-322
Number of pages23
JournalMolecules
Volume6
Issue number4
DOIs
StatePublished - Apr 2001

Keywords

  • Biomimetic synthesis
  • Cytotoxicity
  • Electrophilic nitration
  • NMR
  • Pyrido[2,3,4-kl]acridines

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