ChemInform Abstract: Novel Imidazo[4,5‐b]pyridine and Triaza‐benzo[c]fluorene Derivatives: Synthesis, Antiproliferative Activity and DNA Binding Studies.

Abstract

Novel Imidazo[4,5-b]pyridine and Triaza-benzo[c]fluorene Derivatives: Synthesis, Antiproliferative Activity and DNA Binding Studies. -Imidazopyridines (I), (IV), and (VII) are obtained via cyclocondensation between the corresponding diaminopyridines and acrylic acids and by condensation between methylimidazopyridines and cyanobenzaldehyde, resp. Their cyclic successors, triaza-benzofluorenes (II), (VI), and (VIII) are prepared by dehydrohalogenation cyclization at high temperature or by photochemical dehydrocyclization. Pinner reaction with derivatives (VIII) yields the hydrochloride salts (X). A preponderance of these compounds exerts strong cytostatic effects on a panel of seven human tumor cell lines. Marked antitumor activities are shown by derivatives (III) and (Xa). DNA interaction studies show that derivatives (VI) and (Xa) bind to DNA in an intercalative mode. -(HRANJEC*, M.; LUCIC, B.; RATKAJ, I.; KRALJEVIC PAVELIC, S.; PIANTANIDA, I.; PAVELIC, K.; KARMINSKI-ZAMOLA, G.; Eur.