In Vitro Antifungal, Anticancer Activities and POM Analyses of a Novel Bioactive Schiff Base 4-(((E)-furan-2-ylmethylidene)amino)p-henol: Synthesis, Characterization and Crystal Structure

The title compound (1), C/sub 11/H/sub 9/NO/sub 2/, was synthesized and characterized by FT-IR, 1H NMR, /sup 13/C NMR spectroscopy, mass spectrometry and single crystal analysis. It was crystallized in a monoclinic system with a space group P21/n. The dihedral angle between the planes of furan and benzene ring is 21.24 (11)Degree. The torsion angle of bridge C-C-N-C is -177.81(15) Degree. The crystal structure is stabilized by intermolecular hydrogen bonds between O-H-N and C-H-O forming a three dimensional network. The synthesized compound was screened for the in vitro antifungal against the Fusarium oxysporum f.sp albedinis FAO fungal strains and showed good activity. It was also tested for the anticancer activities against breast (MDA-MB231) and colorectal (LOVO) cancer cell lines and exhibited IC50 values of 6.9 μg/mL and 14.6 μg/mL, respectively. POM calculations of molecular properties of 1 are in good agreement with the mode of antifungal action of the compound bearing (XδYδ) pharmacophore site. Also it shows a drug score of 43 percent which is an important parameter for the compound possessing the drug character. (author)