2-Nitrobenzohydrazide as a Potent Urease Inhibitor: Synthesis, Characterization and Single Crystal X-ray Diffraction Analysis

2-Nitrobenzohydrazide was efficiently synthesized in two steps by the esterification of 2-nitrobenzoic acid followed by the treatment with hydrazine hydrate in methanol. The structure of 2-nitrobenzohydrazide was established by modern spectro-analytical techniques including FTIR, H-1 and C-13-NMR spectroscopy and unequivocally confirmed by single crystal X-ray diffraction data. 2-Nitrobenzohydrazide crystallized in orthorhombic space group P 21 21 21 with unit cell dimensions a = 4.9764(4) angstrom, b = 12.5280 (3) angstrom, c = 12.8512(1) angstrom, beta = beta = gamma = 90 degrees. A combination of N-H center dot center dot center dot N and N-H center dot center dot center dot O hydrogen bonds stabilized the crystal packing of 3. The synthesized compound 3 was assessed as urease inhibitor against Jack bean urease and the results revealed good inhibitory potency with an IC50 value of 4.25 +/- 0.08 mu M. This inhibition strength was 5-fold higher compared to the reference inhibitor thiourea (IC50 = 21.00 +/- 0.11 mu M). The molecular docking studies of the synthesized inhibitor 3 inside the active pocket of urease revealed several important binding interactions.