Synthesis and antitumor activities of certain novel 2-amino-9-(4-halostyryl)-4H-pyrano[3,2-h]quinoline derivatives

Abstract

A series of (E) 4H-pyrano[3,2-h]quinoline-3-carbonitrile (5a–f) and (E) ethyl 4H-pyrano[3,2-h]quinoline-3-carboxylate (6a–f) derivatives were synthesized by interaction of (E) 2-(4-chloro/bromo/fluorostyryl)-8-hydroxyquinoline (3a–c) with α-cyano-p-chloro/bromocinnamonitriles (4a,b) and ethyl α-cyano-p-chloro/bromocinnamates (4c,d), respectively. Structures of these compounds were established on the basis of IR, 1H NMR, 13C NMR, 13C NMR–DEPT, 13C NMR–APT, and MS data. The new compounds were evaluated for antitumor activities against three different human tumor cell lines MCF-7, HCT, and HepG-2. The results of antitumor evaluation revealed that compounds 5a,d and 6a,c,d inhibited the growth of cancer cells compared to Vinblastine. The structure–activity relationships were discussed.