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 structurally characterized by elemental analysis, IR, UV-Vis 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)º, V = 1534.4(2) ų, 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)º, V = 1545.8(4) ų, 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.