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.

► Two diarylquinoline derivatives were firstly synthesized by a simple one-pot method.
► The two antituberculosis derivatives were confirmed by spectra, X-ray diffraction.
► The two new derivatives were also optimized by a DFT method.
► The experimental and computational study of bond lengths and angles were contrasted.
► The result can understand diarylquinoline molecular structure and discover inhibitor.