Synthesis, crystal structures and urease inhibition of N'-(2-bromobenzylidene)-2-(4-nitrophenoxy) acetohydrazide and N'-(4-nitrobenzylidene)-2-(4-nitrophenoxy)acetohydrazide

Abstract

Two new hydrazone compounds, N'-(2-bromobenzylidene)-2-(4-nitrophenoxy)acetohydrazide (1) and N'-(4-nitrobenzylidene)- 2-(4-nitrophenoxy)acetohydrazide (2), were prepared and characterized by elemental analysis, IR, UVVis and 1H NMR spectroscopy, and single-crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic space group P21/n with unit cell dimensions of a = 5.3064(5) Å, b = 18.202(2) Å, c = 15.970(2) Å, β = 95.866(3)°, V = 1534.4(2) Å;3, Z = 4, R1 = 0.0457, and wR2 = 0.0975. Compound 2 crystallizes in the monoclinic space group P21/c with unit cell dimensions of a = 4.6008(7) Å, b = 14.451(2) Å, c = 23.296(3) Å, β = 93.620(2)°, V = 1545.8(4) Å;3, Z = 4, R1 = 0.0441, and wR2 = 0.0985. Structures of the compounds are stabilized by hydrogen bonds and π⋯π interactions. The urease inhibitory activities of the compounds were studied. Both compounds show strong urease inhibitory activities, with IC50 values of 8.4 and 20.2 μM, respectively.