Abstract
Several 4H-pyrano[3,2-h]quinoline (3a-d, 4a, 7a,b, 9a-c, 10a,b, 11a,b, and 13a-c) and 7H-pyrimido[4',5':6,5]pyrano[3,2-h]quinoline derivatives (8a-c) were obtained by treatment of 8-hydroxyquinoline (1a) and 8-hydroxy-2-methylquinoline (1b) with alpha-cyano-p-chloro/bromocinnamonitrile (2a,b) or 4H-pyrano[3,2-h]quinoline derivatives (3a,c,d) with different electrophilic reagents followed by nucleophilic reagents. Structures of these compounds were established on the basis of spectral data. The antitumor activity of the synthesized compounds was investigated in comparison with Vinblastine. Among them, compounds 3c,d, 4a, 8b, 9b,c, 11a,b, and 13a,c inhibited the growth of cancer cells compared to Vinblastine. The structure-activity relationships were discussed.