Synthesis, crystal structure and biological activity of 6-(3-chloropropoxy)-4-(2-fluorophenylamino)-7-methoxyquinazoline

摘要

The title compound, 6-(3-chloropropoxy)-4-(2-fluorophenylannino)-7-nnethoxyquinazoline, was synthesized by selective nucleophilic attack at C-1 of 1-bronno-3-chloropropane by the potassium salt of 4-(2-fluorophenylamino)-7-methoxyquinazolin-6-ol, which was prepared from 7-nnethoxy-4-oxo-3,4-dihydroquinazolin-6-yl acetate in three steps. The compound crystallized as an ethyl acetate complex (C20H21CIFN3O3, M-r = 405.85), and X-ray crystallography showed that the crystal belongs to the orthorhombic system, space group Pbca with a = 12.7407(4)angstrom, b = 14.0058(5)angstrom, c = 21.7726(7)angstrom, alpha = 90 degrees, beta=90 degrees and gamma=90 degrees. The whole molecule is stacked into a three-dimensional structure via weak N-H center dot center dot center dot N hydrogen bonding between molecules. The compound acts as an effective inhibitor on the proliferation of a lung cancer cell line.