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Synthesis, Crystal Structures and Urease Inhibition of N'-(2-Bromobenzylidene)-2-(4-nitrophenoxy)acetohydrazide and N'-(4-Nitrobenzylidene)-2-(4-nitrophenoxy)acetohydrazide

Gui-Hua Sheng, Xiang-Fei Chen, Jian Li, Jie Chen, Ying Xu, Yan-Wei Han, Ting Yang, Zhonglu You, Hai-Liang Zhu

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) Å3, 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) Å3, 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.

Keywords


Hydrazone; Crystal structure; Hydrogen bonds; X-ray diffraction; Urease inhibition.

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DOI: http://dx.doi.org/10.17344/acsi.2015.1770

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Copyright (c) 2015 Gui-Hua Sheng, Xiang-Fei Chen, Jian Li, Jie Chen, Ying Xu, Yan-Wei Han, Ting Yang, Zhonglu You, Hai-Liang Zhu

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