Synthesis of 2-amino-8-chloro-4-phenyl-5,11-dihydro-6H-pyrido[2,3-a]carbazole-3-carbonitrile: Structural and biological evaluation

The title compound 2-amino-8-chloro-4-phenyl-5,11-dihydro-6H-pyrido[2,3-a]carbazole-3-carbonitrile was prepared in good yield by multicomponent reaction under l-proline as promoter structure of the prepared compound was studied and characterized using IR, 1H and 13C NMR spectroscopic techniques. The crystal structure of the compound was determined by X-ray diffraction on single crystals. The spectroscopic experimental evidences strongly suggested that the compound could interact with calf thymus DNA (CT-DNA) through intercalation. The cytotoxicity was evaluated by Sulforhodamine B assay against A-549, B16F10, HCT-15, SKMel2 and SKOV3 cell lines and compared with standard drug cisplatin. The title compound bearing the chloro group depicted better and selective cytotoxicity against SKMel2 cell line. The compound showed moderate capacity for scavenging DPPH.

► Synthesis and characterization of novel pyrido[2,3-a]carbazoles.
► Crystal structure description.
► DNA binding and intercalation.
► Cytotoxicity against 5 cancer cell line A-549, B16F10, HCT-15, SKMel2 and SKOV3 cell lines.
► Free radical scavenging capacity.