Crystal structure of 6,7-dimethoxy-1-(4-nitrophenyl)quinolin-4(1H)-one: a molecular scaffold for potential tubulin polymerization inhibitors

Abstract

The protein tubulin is central for maintaining normal cellular processes, and molecules interfering with the tubulin dynamics have potential in the treatment of cancerous diseases. The title compound, C17H14N2O5, was prepared as a lead compound in a project dedicated to the development of therapeutic agents binding to the colchicine binding site on tubulin, thereby interfering with the cell division in cancer cells. It holds many of the main structural characteristics for colchicine binding and has the potential for further modification and functionalization. In the title molecule, the benzene ring is inclined to the quinoline ring by 76.10 (8)°. In the crystal, molecules are linked by two pairs of C—H...O hydrogen bonds, forming tubular-like arrangements, propagating along the direction of the diagonals of theabplane, and enclosingR22(26) andR22(16) ring motifs.