Crystal structure, Hirshfeld and electronic transition analysis of 2-[(1H-benzimidazol-1-yl)meth-yl]benzoic acid.

In the title compound, C15H12N2O2, the benzimidazole ring system is inclined to the benzene ring by 78.04 (10)°. The crystal structure features O-H⋯N and C-H⋯O hydrogen bonding and C-H⋯π and π-π inter-actions, which were investigated using Hirshfeld surface analysis.

Potential Third-Order Nonlinear Optical Response Facilitated by Intramolecular Charge Transfer in a Simple Schiff Base Molecule: Experimental and Theoretical Exploration.

A Schiff base, namely, 4-[(2-hydroxy-3-methoxybenzylidene) amino] benzoic acid (L1), has been synthesized by the condensation reaction. It has been characterized by Fourier transform infrared spectroscopy , UV-vis spectroscopy, single-crystal X-ray diffraction, and DFT/B3LYP calculations. Single-crystal X-ray crystallographic analysis revealed that L1 exists in the zwitterionic (N-H···...O) form. The supramolecular interactions were investigated by Hirshfeld surface analysis. In addition, third-order nonlinear optical (NLO) properties of L1 were also investigated. The nonlinear refractive index (n2), nonlinear absorption coefficient (ß), and the third-order NLO susceptibility (χ(3)) have been estimated at different concentrations and at different laser powers using close and openaperture Z-scan data. The values of the parameters were found to be varying almost linearly with concentration and power. The present study revealed the utility of the material for various optoelectronic devices such as optical switches, optical data storage devices, and optical sensors. The optical limiting study reveals that this material can also be exploited as an instrument protector from unwanted laser illumination. Furthermore, the NLO behavior of L1 has also been studied by B3LYP/6-311++G(d,p) results.

Ligand substituent effect on the cytotoxicity activity of two new copper(ii) complexes bearing 8-hydroxyquinoline derivatives: validated by MTT assay and apoptosis in MCF-7 cancer cell line (human breast cancer).

In this study, we have examined the effect of ligand substituent on the structure-cytotoxicity relationships of the MCF-7 cancer cell line (human breast cancer), by two copper(ii) complexes {[Cu(qmbn)(Hqmba)(q)]·NO3·2H2O} (1) and {[Cu(Hqmba)2(q)]·NO3·2H2O} (2) (where, qmbn = 2-(quinolin-8-yloxy)(methyl) benzonitrile (L1); Hqmba = 2-((quinolin-8-yloxy)methyl)benzoic acid (L2) and q = quinolin-8-olate). The structural analysis reveals that both the complexes exhibit distorted octahedral (CuN3O3) configuration which is further corroborated by density functional theory (DFT) calculations. The cytotoxicity impact of ligands (L1 and L2) and complexes (1 and 2) was screened against the MCF-7 cell line (human breast cancer). The MTT assay uptake indicated that the presence of -COOH functionality in complex 2 leads to higher cytotoxicity (lower IC50) than that observed for complex 1 containing a -CN group. This could be due to the strong H-bonding forming propensity of the carboxylic acids. Incubation of MCF-7 cancer cells with IC50 concentrations of 1 and 2 promoted cellular detachments via nuclear condensation and membrane destabilization followed by apoptosis as a result of metal-assisted generation of reactive oxygen species. Flow cytometry analysis showed that 1 and 2 might prompt early apoptosis in MCF-7 cells as the maximum percentage of cells appeared in the LR quadrant. Furthermore, mRNA expression analysis confirmed that both the complexes induced apoptosis in MCF-7 cells. Comparative mRNA expression analysis of complexes with their respective ligands also confirmed the enhanced apoptotic behavior of complexes. Furthermore, molecular docking studies of the complexes have also been performed with the active site of EGFR kinase receptors (major target for any cancer causing agent) due to similar analogues with FDA-approved EGFR inhibitors in order to rationalize its promising cytotoxicity activity.

Evaluation of catacholase mimicking activity and apoptosis in human colorectal carcinoma cell line by activating mitochondrial pathway of copper(II) complex coupled with 2-(quinolin-8-yloxy)(methyl)benzonitrile and 8-hydroxyquinoline.

To evaluate the cytotoxic potential of metal-based chemotherapeutic candidate towards the colorectal cancer, we have synthesized a new copper(II) complex [Cu(qmbn)(q)(Cl)] (1) (where, qmbn = 2-(quinolin-8-yloxy)(methyl)benzonitrile and q = 8-hydroxyquinoline) and structurally characterized by single crystal X-ray, Powder-XRD, FTIR and thermogravimetric analysis (TGA). The structural analysis reveals that copper(II) ions exist in a distorted square pyramidal (τ = ~0.1), with ligation of a chloride ion, oxygen atom and two nitrogen atoms at equatorial position and one oxygen atom at apical position. The cytotoxicity potential of complex 1 was executed against human colorectal cell lines (HCT116), which showed that 1 induces mitochondrion-mediated apoptotic cell death via activation of the Bax (pro-apoptotic protein) caspases-3 and 9 proteins. Interestingly, complex 1 was found to be a good candidate as electron-transfer catalyst which mimics catacholase with high turnover frequency (kcat = 1.03 × 102 h-1) for the conversion of the model substrate 3,5-di-tertbutylcatechol (3,5-DTBC) to 3,5-di-tertbutylquinone (3,5-DTBQ). Furthermore, molecular docking studies revealed that complex 1 was successfully localized inside the binding pocket of protein kinase (Akt), which validate the mechanism and mode of interaction of 1 that displayed cytotoxic activity experimentally. The obtained outcomes reveal that the complex 1 could be utilized as an encouraging perspective in the development of new therapeutic candidate for colon cancer.

Crystal structure and Hirshfeld surface analysis of diethyl 5-(2-cyano-phen-oxy)isophthalate.

The title compound, C19H17NO5, obtained by ether bond formation between the reagents, crystallizes in the monoclinic space group P21/c. The compound is non-planar, subtending a dihedral angle of 82.38 (4)° between the plane of hy-droxy isophthalate-based ester and that of the benzo-nitrile moiety. The mol-ecule is bent at the ether linkage, with a Car-yl-O-Car-yl bond angle of 116.74 (11)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds and other weak inter-actions forming a supra-molecular framework. A Hirshfeld surface analysis was performed to generate two-dimensional fingerprint plots, which reveal the type of inter-actions occurring in the vicinity of the mol-ecule.

Crystal structure of 4-(2-hy-droxy-3-meth-oxy-benzyl-amino)-benzoic acid di-methyl-formamide monosolvate monohydrate.

The title compound, C15H15NO4·C3H7NO·H2O, a secondary amine mol-ecule, is accompanied by one equivalent of water and one equivalent of di-methyl-formamide (DMF) as solvents. The mol-ecule is non-planar, with a Car-yl-CH2-NH-Car-yl torsion angle of -66.3 (3)°. In the crystal, O-H⋯O and N-H⋯O hydrogen-bonding inter-actions between the amine mol-ecules and the two types of solvent mol-ecule result in the formation of a layered structure extending parallel to (010).

Crystal structure of 4-[(2-hy-droxy-3-meth-oxy-benz-yl)amino]-benzoic acid hemihydrate.

In the crystal of the title vanilline derivative, 2C15H15NO4·H2O, the secondary amine mol-ecule is accompanied by half equivalent of water. The mol-ecule is non-planar, with torsion angle Car-yl-CH2-NH-Car-yl of -83.9 (2)°. In the crystal, the system of O-H⋯O hydrogen bonds, including bridging water mol-ecules residing on crystallographic twofold axes, results in a two-dimensional layered structure. Within the layers, there are also weak N-H⋯π inter-actions involving the vanilline benzene ring.

Crystal structure of 4-[(3-meth-oxy-2-oxidobenzyl-idene)azaniumyl]-benzoic acid methanol monosolvate.

In the crystal of the title compound, C15H13NO4·CH3OH, the Schiff base mol-ecule exists in the zwitterionic form; an intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular structure. The benzene rings are nearly co-planar, subtending a dihedral angle of 5.34 (2)°. In the crystal, classical O-H⋯O and weak C-H⋯O hydrogen bonds link the Schiff base mol-ecules and methanol solvent mol-ecules into a three-dimensional supra-molecular architecture. The crystal studied was refined as an inversion twin.