Synthesis and Electrophilic Substitution of Pyrido[2,3,4-kl]-acridines

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.

Keywords

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