Synthesis, crystal, computational study and in vitro anti-tuberculosis activity of N-(furan-2-yl-methyl)-N-(phenyl(quinolin-3-yl)methyl) acetamide derivatives

A one-pot synthesis of N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl)methyl)- N-(furan-2-yl-methyl)-2-morpholinoacetamide (1) and N-((6-bromo-2- methoxyquinolin-3-yl)(phenyl)methyl)-N-(furan-2-yl-methyl)-2-adamantylacetamide (2) was achieved in good yield for the first time. Compounds 1 and 2·H₂O were characterized by single crystal X-ray diffraction in solid state. The structures of two new derivatives have been confirmed by typical spectroscopic techniques, namely IR, ¹H and ¹³C NMR. The optimized geometric bond lengths and bond angles obtained by using density functional theory (DFT) have been compared with X-ray diffraction values. The experimental molecular structures are well reproduced by the computation. The geometrical parameters of the title compounds are similar to those of some reported derivatives. In addition, in vitro anti-tuberculosis activities of derivatives 1 and 2 were also investigated.