Antitumor acridines with diaminoalkylo pharmacophoric group*
Technical University of Gdansk, Department of Pharmaceutical
Technology and Biochemistry, 80-952 Gdansk, Poland
Abstract: The substitution of acridine molecule in positions
1 and/or 4 with diaminoalkylo residue may result in obtaining derivatives
displaying antitumor activity. The diaminoalkylo residue can be attached
to acridine either directly or indirectly as a carboxamido moiety. In
the former case, the presence of appropriate substituent in position
para to diaminoalkylo residue is crucial for antitumor activity. Also,
heterocyclic aromatic rings condensed with the acridine core can be
considered as such substituents. Additional substituents introduced
into the acridine core, especially those that may be transformed into
quinoid systems, significantly increase antitumor activity of modified
analogs. It is, however, of utmost importance that the presence of diaminoalkylo
residue is the indispensable prerequisite for biological activity of
acridines. Among several groups of synthesized diaminoalkyloacridines,
the most potent antineoplastic properties toward a wide spectrum of
transplantable tumors are exhibited by acridine-4-carboxamides, imidazo-,
triazolo-, and pyrazoloacridinones. Two derivatives belonging to the
above groups, acridine-4-carboxamide DACA and imidazoacridinone C-1311,
are currently in clinical trials. Other derivatives exhibiting potent
antitumor activity, that could be considered as close analogs of diaminolkyloacridines,
are pyrazoloacridines, one of which is currently under clinical evaluation.
*Plenary lecture presented at the Hungarian-German-Italian-Polish
Joint Meeting on Medicinal Chemistry, Budapest, Hungary, 2 6 September
2001. Other presentations are published in this issue, pp.
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