Synthesis, spectroscopic characterization, X-ray powder structure analysis, DFT study and in vitro anticancer activity of N-(2-methoxyphenyl)-3-methoxysalicylaldimine

Abstract

Schiff base, N-(2-methoxyphenyl)-3-methoxysalicylaldimine (MPMS), was synthesized and characterized by spectroscopic methods. Crystal structure of the title compound crystallizing in the orthorhombic space group P ca2 1, a = 23.695(2), b = 7.7011(8), c = 7.3570(9) Å, V = 1342.5(2) Å 3, Z = 4 has been solved from X-ray powder diffraction data following direct-space approach and refined by the Rietveld method. In solid state, the salicylaldimine compound exists as a phenol-imine tautomer with a strong intramolecular O–H…N hydrogen bond. The molecular geometry and electronic structure of MPMS were calculated at the DFT level using the hybrid exchange-correlation functional, BLYP. The optimized molecular geometry corresponds to the non-planar conformation of the molecule as established by the crystallographic analysis. The anticancer activity of the title Schiff base was evaluated against three different cell lines, SF-268, MCF-7 and NCI-H460.