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

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 10 (1) over bar plane which are in turn linked by fifth C-H...O interactions, along b-axis. Interlayers pi...pi 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. (C) 2021 Elsevier B.V. All rights reserved.

Automated summary

The title compound with three independent molecules in the asymmetric unit forms a compact 3D supramolecular structure through hydrogen bonding. Molecular docking techniques were used to study interactions with proteins and interpret cytotoxic activities against cancer cell lines. Strong interactions were observed between the title compound and a closely related structure with modifications at position 5 in the pyrazole ring.