Crystal Structure and Hirshfeld Surface Analysis of 1-(4-Chlorophenyl)-5-{4-[(2-methylphenyl)methoxy]phenyl}-1<i>H</i>-Pyrazole

Abstract

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.

Vicinal Diaryl-Substituted Isoxazole and Pyrazole Derivatives with In Vitro Growth Inhibitory and In Vivo Antitumor Activity

“…According to the SAR results, compound 11 with 3,4diarylisoxazole and compound 85 with 1,5-diarylpyrazole frameworks were selected for further analysis, and unambiguous structural elucidation of 11 and 85 using the single-crystal X-ray diffraction method was accomplished showing the accurate rearrangement of aromatic rings and atoms in 3Dshape (Figure S1). 29,30 Next, judged by the cellular activity of 11 and 85, both compounds in addition to Huh7, Mahlavu, and MCF7 cell lines were further screened against a panel of the hepatocellular carcinoma (HepG2, SNU475, Hep3B, FOCUS, Hep40, and PLC-PRF-5) and breast cancer (MDA-MB-231, MDA-MB-468, SKBR3, and ZR-75) cell lines along with the nontumorigenic immortalized breast epithelial cells MCF10A (Table 5). The results demonstrated that both compounds are endowed with potent antiproliferative activity against all cancer cells with IC 50 values in the range of 1.3−9.5 μM for 11 and 0.77−7.8 μM for 85 for hepatocellular carcinoma and breast cancer cell lines, while found less toxic to the MCF10A immortalized normal breast epithelial cells (Table 5).…”

“…According to the SAR results, compound 11 with 3,4-diarylisoxazole and compound 85 with 1,5-diarylpyrazole frameworks were selected for further analysis, and unambiguous structural elucidation of 11 and 85 using the single-crystal X-ray diffraction method was accomplished showing the accurate rearrangement of aromatic rings and atoms in 3D-shape (Figure S1). , …”

“…13 C NMR (100 MHz, CDCl 3 ): δ C 11.56, 52.15, 69.32, 114.53, 114.91, 121.74, 126.97, 129.02, 129.04, 129.81, 129.90, 131.10, 133.73, 141.75, 159.45, 160.51, 166.59, 166.77. HRMS (m/z) [M + H] + calcd for C 25 H 21 NO 4 Cl: 434.1159, found: 434.1161-5-methylisoxazol-3-yl)phenoxy)methyl)benzoic acid (29). Compound 28 (1.0 equiv) was stirred with LiOH.H 2 O (3.0 eq) in a THF:water solvent system under reflux for 3 h. At the end of the period, the reaction mixture was acidified with concentrated HCl and the precipitate formed was filtered under vacuum by washing with water.…”