Synthesis, crystal, calculated structure and biological activity of N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl) methyl)-N-(1-adamantyl)-3- (dimethylamino) propanamide

The halogenated hydrocarbon amination reaction between the original raw material N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl)methyl)-3-chloro-N-(1- adamantyl) propanamide and dimethylamine hydrochloride produces the target molecule N-((6-bromo-2-methoxyquinolin-3- yl)(phenyl)methyl)-N-(1-adamantyl)-3- (dimethylamino) propanamide (C ₃₂H ₃₈BrN ₃O ₂, M _r = 576.56), and its structure was confirmed by elemental analysis, IR, ¹H NMR, MS, and X-ray diffraction. This crystal is of monoclinic system, space group P2 ₁/c with a = 10.760(5), b = 14.768(5), c = 19.635(5) Å, β = 113.969(16)°, V = 2851.0(18) Å ³, Z = 4, D _c = 1.343 g/cm ³, F(000) = 1208, μ(MoKα) = 1.475 mm ^-1, the final R = 0.0645 and wR = 0.2039. In total, 4681 independent reflections including 3164 observed ones with I > 2σ(I) were collected. The dihedral angle between substituted quinolyl and phenyl is 64.0°. Through C- H···O, C-H···N and C-H···Br weak hydrogen bonds among molecules, the whole molecule is stacked into a three-dimensional structure. The optimized geometric bond lengths and bond angles obtained by using density functional theory (DFT) have been compared with X-ray diffraction values. In addition, the preliminary biological test showed that the title compound has anti-Mycobacterium phlei 1180 activity.