Synthesis, structural characterization and biological activity of fluorinated Schiff-bases of the type [C6H4-1-(OH)-3-(CH=NArF)]

A series of fluorinated imines of the type [C6H4-1-(OH)-3-(CH=NArF)]; Ar-F=C6H4-4-F (1), C6H3-2,3-F-2 (2), C6H3-3,5-F-2 (3), C6H2-2,4,6-F-3 (4), C6H4-3-CF3 (5), C6H3-3,5-(CF3)(2) (6), were synthesized and fully characterized including single crystal X-ray diffraction analyses of compounds [C6H4-1-(OH)-3-(CH=NC6- H-4-4-F)] (1), [C6H4-1-(OH)-3-(CH=Nc(6)H(3)-3,5-F-2)] (3), [C6H4-1-(OH)-3-(CH=NC6H4-3-CF3)] (5). Further analyses of these results allowed the identification of the predominant non-covalent interactions and supramolecular arrangements in the solid state. Exploration of the anti-bacterial activity against both gram-positive and gram-negative bacteria showed those compounds including F or CF3 substituents at the meta positions i.e. [C6H4-1-(OH)-3-(CH=NC6H3-3,5-F-2)] (3), [C6H4-1-(OH)-3-(CH=NC6H4-3-CF3)] (5), [C6H4-1-(OH)-3-(CH=NC6H3-3,5-(CF3)(2))] (6), to be the best when their activity is compared versus ampicillin. (C) 2015 Elsevier B.V. All rights reserved.