In the title compound, C24H20ClNO2, the mean planes of 4-chlorophenyl, 2-methylphenyl and phenylene rings make dihedral angles of 62.8 (2), 65.1 (3) and 15.1 (2)°, respectively, with the 5-methyl-1,2-oxazole ring. In the crystal, molecules are linked by intermolecular C—H...N, C—H...Cl, C—H...π contacts and π–π stacking interactions between the phenylene groups. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (48.7%), H...C/C...H (22.2%), Cl...H/H...Cl (8.8%), H...O/O...H (8.2%) and H...N/N...H (5.1%) interactions.

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The aim of the study is to explore the crystal structure and performe Hirshfeld surface analysis of 1-(4-chlorophenyl)-5-{4-[(2-methylphenyl)methoxy]phenyl}-1H-pyrazole.In the title compound, C23H19ClN2O, the 4-chlorophenyl, 2-methylphenyl and benzene rings are oriented with dihedral angles of 71.22(10), 31.82(9) and 59.76( 9)°, respectively, with respect to the pyrazole ring. Pairs of molecules are linked by intermolecular C-H•••O hydrogen contacts with R 2 2(8) ring motifs forming sheets lying parallel to (100). Furthermore C-H•••π interactions also contribute to stabilizing the molecular packing. A Hirshfeld surface analysis has been used to confirm and quantify the supramolecular interactions which indicate that the most important contributions for the crystal packing are from H•••H (42.5%) and H•••C/C•••H (35%) and H•••Cl/Cl•••H (12%) interactions.

Rho kinase (ROCK), an enzyme belonging to the serine-threonine kinase family, is involved in the regulation of basic cellular processes such as morphology, movement, division, differentiation and apoptosis. On the other hand, excessively activated ROCK can cause to cardiovascular and neurological disorders or cancer. In recent years, overactivation of Rho kinases has been associated with increased metastasis in various tumor types and has been explored as target for the development of new anticancer drugs. We report here the design and synthesis of five urea derivatives in search of novel inhibitors of cancer cell migration. Compounds evaluated for their cytotoxic activities against breast (MCF-7) cancer cell line. After determination of the ineffective concentrations of compounds on the proliferation of MCF-7 cells, wound healing experiments were conducted to investigate the antimigratory effects of compounds. While compounds 4 and 10 had no effect on cell migration, treatment of MCF-7 cells with compounds 5, 8 and 9 resulted in significant reduction in cell motility. Taken together our results suggest that the newly synthesized compounds 5, 8 and 9 had the potential antimigratory activity through possible ROCK inhibition in cancer cells.

Soluble epoxide hydrolase (sEH) metabolizes epoxyeicosatrienoic acids (EETs), which are endowed with beneficial biological activities as they reduce inflammation, regulate endothelial tone, improve mitochondrial function, and decrease oxidative stress. Therefore, inhibition of sEH for maintaining high EET levels is implicated as a new therapeutic modality with broad clinical applications for metabolic, renal, and cardiovascular disorders. In our search for new sEH inhibitors, we designed and synthesized novel amide analogues of the quinazolinone-7carboxylic acid derivative 5, a previously discovered 5-lipoxygenase-activating protein (FLAP) inhibitor, to evaluate their potential for inhibiting sEH. As a result, we identified new quinazolinone-7-carboxamides that demonstrated selective sEH inhibition with decreased FLAP inhibitor properties. The tractable SAR results indicated that the amide and thiobenzyl fragments flanking the quinazolinone nucleus are critical features governing the potent sEH inhibition, and compounds 34, 35, 37, and 43 inhibited the sEH activity with IC 50 values of 0.30−0.66 μM. Compound 34 also inhibited the FLAP-mediated leukotriene biosynthesis (IC 50 = 2.91 μM). In conclusion, quinazolinone-7-carboxamides can be regarded as novel lead structures, and newer analogues with improved efficiency against sEH along with or without FLAP inhibition can be generated.