Crystal structure of 6,7-dimeth-oxy-1-(4-nitro-phen-yl)quinolin-4(1H)-one: a mol-ecular scaffold for potential tubulin polymerization inhibitors.
The protein tubulin is central for maintaining normal cellular processes, and mol-ecules inter-fering 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 inter-fering 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 mol-ecule, the benzene ring is inclined to the quinoline ring by 76.10 (8)°. In the crystal, mol-ecules 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.
Department of Pharmaceutical Chemistry, University of Oslo, PO Box 1068 Blindern, N-0371 Oslo, Norway.
Vegard Torp
VT
Lien
Department of Pharmaceutical Chemistry, University of Oslo, PO Box 1068 Blindern, N-0371 Oslo, Norway.
Dag Erlend
DE
Olberg
Department of Pharmaceutical Chemistry, University of Oslo, PO Box 1068 Blindern, N-0371 Oslo, Norway.
Jo
J
Klaveness
Department of Chemistry, University of Oslo, PO Box 1033 Blindern, N-0315 Oslo, Norway.
Carl Henrik
CH
Görbitz
N-substituted quinolone; crystal structure; cytotoxic agents; hydrogen bonding; tubulin polymerization