Synthesis, Crystal, Calculated Structure and Biological Activity of N-（（6-bromo-2-methoxyquinolin-3-yl）（phenyl） methyl）-N-（1-adamantyl）-3-（dimethylamino） Propanamide

摘要

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 （C32H38BrN3O2, Mr = 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 P21/c with a = 10.760（5）, b = 14.768（5）, c = 19.635（5）, β = 113.969（16）°, V = 2851.0（18）3, Z = 4, Dc = 1.343 g/cm3, 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.