Crystal structure of 1-(1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)-3,5-diphenyl-1H-pyrazole and molecular docking studies of 1-(1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)-3,5-diphenyl-1H-pyrazole and 5-methyl-1-(1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)-3-phenyl-1H-pyrazole towards tyrosine kinases

Abstract

The title compound, C20H17N5O2, crystallizes with three independent molecules (A, B and C) in the asymmetric unit with almost identical geometrical parameters. The molecules are far from planar as a result of steric repulsion between the rings. In the crystal, the A, B and C molecules are linked by a pair of C—H···O and one C—H···N hydrogen bonds forming A, B and C trimer. These trimers are further linked by a fourth C—H···N hydrogen bond, forming layers that stack along 101¯ plane which are in turn linked by fifth C—H···O interactions, along b-axis. Interlayers π···π interactions between different pyrazole rings of two molecules add extra lattice supramolecularity. All interactions form a compact 3D supramolecular structure. Molecular docking techniques are carried out to explore the interactions of the title compound and closely related structures with bcr/abl and epidermal growth factor receptor tyrosine kinases (EGFR and HER2) to interpret the cytotoxic activities of some of them toward K562 and MCF-7 cancer cell lines. Results of the molecular docking reveal strong interactions between the title compound and one of the closely related structure (muting the phenyl group to methyl at position 5 in pyrazole ring) with the studied proteins.