Synthesis, Characterization, X-Ray Crystal Study and Bioctivities of Pyrazole Derivatives: Identification of Antitumor, Antifungal and Antibacterial Pharmacophore Sites

Abstract The reaction of hydroxymethyl pyrazole derivatives with one equivalent of the appropriate primary amine yields N-((1h-pyrazol-1-yl) methyl) pyrimidin-2-amine (L1), 2-(((1h-pyrazol-1-yl) methyl) amino) benzoic acid (L2), and ethyl 5-methyl-1-(((6-methyl-3-nitropyridin-2-yl) amino) methyl)-1h-pyrazole-3-carboxylate (L3). The structure of synthesized compounds (L1-L3) was identified by FT-IR, UV-visible, proton NMR spectroscopy, mass spectroscopy, and single crystal X-ray crystallography. The armed pyrazoles (L1-L3) were crystallized in the space groups C2/c, P21/n and P-1 for L1, L2, and L3 respectively. Crystallographic analysis revealed that N-H of the amine group and Nitrogen or Oxygen atoms are in-plane with the aromatic ring. The aminomethyl chain forms a distorted second plane. The angle between the two planes is observed to be 76.07° (N2-C7-N5-N19) for L1, 62.12° (N34-C63-N22-N35) for L2, 60.84° (N3-C8-N2-N1), and 0.41° (N1-C4-C3-O1/O2) for L3 was studied. Theoretical physical and chemical properties calculations have been performed on the studied armed pyrazoles (L1-L3) using three different programs: Petra, Osiris, & Molinspiration (POM). The geometric parameters of the optimized structure are in agreement with the experimental data obtained from the X-ray structures. The origin of the biological activity against breast cancer and microbes has also been confirmed.