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Abstract In this study, a two pyrazole derivatives; 2-(5-methyl-1H-pyrazole-3-carbonyl)-N-phenylhydrazine-1-carboxamide (Pyz-1) and 4-amino-5-(5-methyl-1H-pyrazol-3-yl)-4H-1,2,4-triazole-3-thiol (Pyz-2) were synthesized and characterized by 13C-NMR, 1H-NMR, FT-IR, and mass spectrometry. A complete molecular structures optimization, electronic and thermodynamic properties of Pyz-1 and Pyz-2 in gas phase and aqueous solution were predicted by using hybrid B3LYP method with the 6-311++G** basis sets. Pyz-1 and Pyz-2 were evaluated in vitro for their anti-diabetic, antioxidant and xanthine oxidase inhibition activities. For anti-diabetic activity, Pyz-1 and Pyz-2 showed a potent α-glucosidase and α-amylase inhibition with IC50 values of 75.62 ± 0.56, 95.85 ± 0.92 and 119.3 ± 0.75, 120.2 ± 0.68 µM, respectively, compared to Acarbose (IC50(α-glucosidase) = 72.58 ± 0.68 µM, IC50(α-amylase) = 115.6 ± 0.574 µM). In xanthine oxidase assay, Pyz-1 and Pyz-2 exhibited remarkable inhibitory ability with IC50 values 24.32 ± 0.78 and 10.75 ± 0.54 µM, respectively. The result of antioxidant activities showed that the title compounds have considerable antioxidant and radical scavenger abilities. In addition, molecular docking simulation was used to determine the binding modes and energies between the title compounds and α-glucosidase and α-amylase enzymes.

This study investigates, in the first part, the synthesis and purification of a poorly crystalline hydroxyapatite (HAp) using natural Moroccan phosphate (Boucraa region) as a raw material. Despite its successful preparation, the obtained HAp was contaminated by several metallic cations (mostly Cd, Pb, Sn, Ti, Mn, Mg, Fe, and Al) migrated from the natural rocks during the digestion process, inhibiting HAp application in several sectors. To minimize the existence of these elements, the dissolution–precipitation technique (DP) was investigated as a non-selective purification process. Following the initial DP cycle conducted on the precipitated HAp, the removal efficiency was approximately 60% for Al, Fe, Mg, Mn, and Ti and 90% for Cd and Pb. After three consecutive DP cycles, notable improvement in the removal efficiency was observed, reaching 66% for Fe, 69% for Mg, 73% for Mn, and 74% for Al, while Cd, Pb, and Ti were totally removed. In the second part of this study, the purified HAp was digested using sulfuric acid to produce high-quality phosphoric acid (PA) and gypsum (GP). The elemental analysis of the PA indicates a removal efficiency of approximately 89% for Fe and over 94% for all the examined cations. In addition, the generated GP was dominated by SO3 and CaO accompanied with minor impurities. Overall, this simple process proves to be practically useful, to reduce a broad spectrum of cationic impurities, and to be flexible to prepare valuable products such hydroxyapatite, phosphoric acid, and gypsum.

Pyrazole, characterized by a five-membered heterocyclic structure featuring two neighboring nitrogen atoms, serves as a core element. Pyrazoles hold a privileged status as versatile frameworks in various sectors of the chemical industry, including medicine and agriculture. Previous reviews have extensively highlighted the significance of pyrazoles and their diverse biological activities, encompassing roles such as antituberculosis, antimicrobial, antifungal, anti-inflammatory, anticancer, and antidiabetic agents. Consequently, they have garnered substantial interest from researchers. The aim of this review is to offer a comprehensive overview of the published research related to the synthesis of pyrazole derivatives, encompassing a discussion of diverse methods for accessing the pyrazole moiety. These methods span from utilizing transition-metal catalysts and photoredox reactions to employing one-pot multicomponent processes, novel reactants, and innovative reaction types. It encompasses studies conducted by numerous scientists worldwide, showcasing collective efforts in advancing the methodologies and applications of pyrazole derivatives.

Despite continual efforts being made with multiple clinical studies and deploying cutting-edge diagnostic tools and technologies, the discovery of new cancer therapies remains of severe worldwide concern. Multiple drug resistance has also emerged in several cancer cell types, leaving them unresponsive to the many cancer treatments. Such a condition always prompts the development of next-generation cancer therapies that have a better chance of inhibiting selective target macromolecules with less toxicity. Therefore, in the present study, extensive computational approaches were implemented combining molecular docking and dynamic simulation studies for identifying potent pyrazole-based inhibitors or modulators for CRMP2, C-RAF, CYP17, c-KIT, VEGFR, and HDAC proteins. All of these proteins are in some way linked to the development of numerous forms of cancer, including breast, liver, prostate, kidney, and stomach cancers. In order to identify potential compounds, 63 in-house synthesized pyrazole-derivative compounds were docked with each selected protein. In addition, single or multiple standard drug compounds of each protein were also considered for docking analyses and their results used for comparison purposes. Afterward, based on the binding affinity and interaction profile of pyrazole compounds of each protein, potentially strong compounds were filtered out and further subjected to 1000 ns MD simulation analyses. Analyzing parameters such as RMSD, RMSF, RoG and protein–ligand contact maps were derived from trajectories of simulated protein–ligand complexes. All these parameters turned out to be satisfactory and within the acceptable range to support the structural integrity and interaction stability of the protein–ligand complexes in dynamic state. Comprehensive computational analyses suggested that a few identified pyrazole compounds, such as M33, M36, M72, and M76, could be potential inhibitors or modulators for HDAC, C-RAF, CYP72 and VEGFR proteins, respectively. Another pyrazole compound, M74, turned out to be a very promising dual inhibitor/modulator for CRMP2 and c-KIT proteins. However, more extensive study may be required for further optimization of the selected chemical framework of pyrazole derivatives to yield improved inhibitory activity against each studied protein receptor.

In the title compound, C18H15ClN3O+·Cl−·2H2O, three intramolecular hydrogen bonds are observed, N—H...O, O—H...Cl and O—H...O. In the crystal, molecules are connected by C—H...Cl and N—H...O hydrogen bonds. Strong C—H...Cl, N—H...O, O—H...Cl and O—H...O hydrogen-bonding interactions are implied by the Hirshfeld surface analysis, which indicate that H...H contacts make the largest contribution to the overall crystal packing at 33.0%.

The title compound, C22H15N3O4, is built up from a central imidazo[1,2-a]pyridine ring system connected to a nitroso group, a phenyl ring and a 2-oxo-2-phenylethyl acetate group. The imidazo[1,2-a] pyridine ring system is almost planar (r.m.s. deviation = 0.017 Å) and forms dihedral angles of 22.74 (5) and 45.37 (5)°, respectively, with the phenyl ring and the 2-oxo-2-phenylethyl acetate group. In the crystal, the molecules are linked into chains parallel to the b axis by C—H...O hydrogen bonds, generating R21 (5) and R44 (28) graph-set motifs. The chains are further linked into a three-dimensional network by C—H...π and π-stacking interactions. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most important contributions for the crystal packing are from H...H (36.2%), H...C/C...H (20.5%), H...O/O...H (20.0%), C...O/O...C (6.5%), C...N/N...C (6.2%), H...N/N...H (4.5%) and C...C (4.3%) interactions.

The title Schiff base, C22H24N2O6, adopts an E configuration. The molecule is planar, the mean planes of the phenyl ring system (r.m.s deviation = 0.0059 Å) forms a dihedral angle of 0.96 (4)° with the mean plane of the phenyl ring moiety (r.m.s deviation = 0.0076 Å). In the crystal, molecules are linked by weak intermolecular C—H...O and C—H...N hydrogen bonds into chains extending along the c-axis and b-axis directions, respectively. A molecular docking study between the title molecule and 5-HT2C, which is a G protein receptor and ligand-gated ion channels found in nervous systems (PDB ID: 6BQH) was executed. The experiment shows that it is a good potential agent because of its affinity and ability to stick to the active sites of the receptor.

The pyridazine ring in the title compound, C20H17ClN2O3, adopts a screw-boat conformation. The whole molecule is flattened, the dihedral angles subtended by the least-squares plane of the central aromatic ring with those of the terminal benzene and pyridazine rings being 15.18 (19) and 11.23 (19)°, respectively. In the crystal, the molecules are linked by pairs of N—H...O bonds into centrosymmetric dimers and by C—H...π contacts into columns. The results of the Hirshfeld surface analysis show that the most prominent interactions are H...H, accounting for 36.5% of overall crystal packing, and H...O/O...H (18.6% contribution) contacts.

In this research, FT-IR, NMR (1H & 13C), mass spectrometry and single-crystal X-ray diffraction has been used to characterize the synthesized 5-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)quinolin-8-ol (DD2) derivative. B3LYP calculations with the 6-31G* and 6–311++G** basis sets have shown that the most stable C2 structure in gas phase and aqueous solution is in agreement with the experimental determined by X-ray diffraction. Higher dipole moments for C2 in aqueous solution, predicted with both methods, are probably related to its higher stability resulting higher volume contraction (ΔV −1.0 Å3) in solution with the B3LYP/6-31G* method. Similar behaviours in the Mulliken and NPA charges but different from MK charges are observed. Bond orders studies reveal that the O15-H16···N17 bonds are present in both media, as was experimentally observed in the solid state. MEP surfaces have evidenced nucleophilic sites on N of triazol ring while weak electrophilic ones on aromatic H of three rings being the H atom of OH the most labile. Gap values support a lower reactivity of C2 in solution, in agreement with the higher stability evidenced by AIM analyses. The higher electronic density on triazol ring could justify that C2 is unstable in solution, as revealed by NBO analyses. Complete assignments of 93 expected vibration normal modes of C2 and a set of scaled force constants were obtained in both media by using harmonic force fields. Comparisons between experimental and theoretical infrared and 1H- and 13C NMR spectra show reasonable concordances. Intermolecular interactions in the crystal packing of DD2 were studied by using Hirshfeld surface analysis. Furthermore, DD2 was investigated against two targets of SARS-CoV-2 (PDB ID: 6WCF and PDB ID: 6Y84) by using molecular docking studies. Finally, drug likeness and ADME properties of DD2 were researched and compared with hydroxychloroquine, remdesivir, oseltamivir, lopinavir, ritonavir molecules associated as SARS-CoV-2 inhibitors.

In this work, we present an efficient one-pot method for the synthesis of three new azo-isoxazoline derivatives (4a–c) from aromatic aldehydes, hydroxylamine hydrochloride and 4-(allyloxy)azobenzene. Thus, the azo-isoxazoline derivatives (4a–c) were synthesized via 1,3-dipolar cycloaddition using sodium dichloroisocyanurate (SDIC) as an eco-friendly and inexpensive oxidizing agent under ultrasound cavitation in water as a green solvent. The desired compounds 4a–c were obtained in high to excellent yields of 75–90%.

Despite the decades of scientific studies for developing promising new therapies, cancer remains a major cause of illness and mortality, worldwide. Several cancer types are the major topic of research in drug discovery programs due to their global incidence cases and growing frequency. In the present study, using two different statistical approaches PCA (principal component analysis) and PLS (partial least squares), six 2D-QSAR (quantitative structure activity relationship) models have been developed for the set of compounds retrieved against seven cancer cell lines vizPC-3, B16F10, K562, MDA-MB-231, A2780, and ACHN. For the creation and validation of 2D-QSAR models, OECD (Organization for Economic Co-operation and Development) requirements have been strictly followed. All of the generated 2D-QSAR models produce a significant and high correlation coefficient value with several other statistical parameters. Moreover, developed 2D-QSAR models have been used for activity predictions of in-house synthesized 63 pyrazole derivatives compounds. Precisely, most statistically significant and accepted2D-QSAR model generated for each cancer cell line has been used to predict the pIC50 value (anti-cancer activity) of all 63 synthesized pyrazole derivatives. Furthermore, designing of novel pyrazole derivatives has been carried out by substituting the essential functional groups based on the best derived 2D-QSAR models for each cancer cell line, more precisely, based on the most significant molecular descriptors with enhanced anti-cancer activity. Finally, the prediction of the new designed molecules reveals higher pIC50 than the standard compounds.

The aim of this work was to scrutinize the physiochemical properties of a new pyridazin-3(2H)-one derivative with potential pharmaceutical effectiveness via density functional theory (DFT) and molecular docking analysis. The compound 2-(2-(4-fluorophenyl)-2-oxoethyl)-6-methyl-5-(4-methylbenzyl)pyridazin-3(2H)-one (FOMMP) was synthesized and characterized by FT-IR, UV-Vis, 1H-NMR, 13C-NMR, ESI-MS, and single-crystal XRD analysis. In addition, the geometrical structure of the molecule was analyzed. Frontier molecular orbital (FMO) analysis showed a low energy gap that suggests the chemical reactivity of the title compound. The electrophilicity index (ω) points towards the probable biological activity of FOMMP. The molecular electrostatic potential (MEP) was used to assess the local reactivity properties and suggests that the nitrogen atom sites are electronegative. Computational and experimental UV-spectral analyses were performed to attain the bandgap associated with electronic transitions while the charge transfer length helped us determine that the excitation mode associated with the electronic transitions is long-ranged. Natural hybrid orbital (NHO) and natural bond orbital (NBO) analyses depicted the prominent acceptor-donor interactions in terms of the stabilization energies. Hirshfeld surface analysis was performed to analyze the intermolecular interactions in the crystal structure. In addition, a molecular docking study was executed to evaluate the potential of the protease inhibitors (PIs) against SARS-CoV-2.

The structure, spectroscopic features, and pharmaceutical effect of N′-(4-Methoxybenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide (MBPPC) has been studied by DFT modeling, X-ray diffraction, FT-IR, 1H and 13C NMR, and molecular docking investigation. Molecular structure analysis was carried out using DFT calculation. Then, the low RMSD value indicates the good agreement between calculated and observed data. In order to understand the electronic charge transition, the electron difference density technical was performed. 1H and 13C NMR spectra were recorded in the region of 0–15 and 5–225 ppm, respectively, and FT-IR spectrum of MBPPC was obtained from 4000 to 500 cm−1. Electronic structure characteristics were achieved at the level of B3LYP/6-311+G(2d,p). Inter and intramolecular interactions are discussed by topological (AIM, RDG) and Hirshfeld surface analyses. TD-DFT calculations were conducted to reveal molecular orbital based reactivity characteristics and nonlinear optical features up to third order. In addition, thanks to the broad biological field of compounds based on pyrazole and hydrazone groups, molecular docking of the title compound was carried out to study their clinical activities. Docking simulation shows the potential of MBPPC against Vibrio cholera, Mycobacterium tuberculosis, and estrogen receptor.

The asymmetric unit of the title compound, C22H31NO3, comprises of one molecule. The molecule is not planar, with the carboxylate ester group inclined by 33.47 (4)° to the heterocyclic ring. Individual molecules are linked by aromaticC—H...Ocarbonyl hydrogen bonds into chains running parallel to [001]. Slipped π–π stacking interactions between quinoline moieties link these chains into layers extending parallel to (100). Hirshfeld surface analysis, two-dimensional fingerprint plots and molecular electrostatic potential surfaces were used to quantify the intermolecular interactions present in the crystal, indicating that the most important contributions for the crystal packing are from H...H (72%), O...H/H...O (14.5%) and C...H/H...C (5.6%) interactions.

Two polymorphs of the title compound, C19H16N2O3, were obtained from ethanolic (polymorph I) and methanolic solutions (polymorph II), respectively. Both polymorphs crystallize in the monoclinic system with four formula units per cell and a complete molecule in the asymmetric unit. The main difference between the molecules of (I) and (II) is the reversed position of the hydroxy group of the carboxylic function. All other conformational features are found to be similar in the two molecules. The different orientation of the OH group results in different hydrogen-bonding schemes in the crystal structures of (I) and (II). Whereas in (I) intermolecular O—H...O hydrogen bonds with the pyridazinone carbonyl O atom as acceptor generate chains with a C(7) motif extending parallel to the b-axis direction, in the crystal of (II) pairs of inversion-related O—H...O hydrogen bonds with an R22(8) ring motif between two carboxylic functions are found. The intermolecular interactions in both crystal structures were analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

In this work, a novel series of pyridazinone derivatives (3–17) were synthesized and characterized by NMR (1H and 13C), FT-IR spectroscopies, and ESI-MS methods. All synthesized compounds were screened for their antibacterial activities against Staphylococcus aureus (Methicillin-resistant), Escherichia coli, Salmonella typhimurium, Pseudomonas aeruginosa, and Acinetobacter baumannii. Among the series, compounds 7 and 13 were found to be active against S. aureus (MRSA), P. aeruginosa, and A. baumannii with the lowest MIC value range of 3.74–8.92 µM. Afterwards, DFT calculations of B3LYP/6-31++G(d,p) level were carried out to investigate geometry structures, frontier molecular orbital, molecular electrostatic potential maps, and gap energies of the synthesized compounds. In addition, the activities of these compounds against various bacterial proteins were compared with molecular-docking calculations. Finally, ADMET studies were performed to investigate the possibility of using of the target compounds as drugs.

The title pyridazinone derivative, C20H18N2O3, is not planar. The phenyl ring and the pyridazine ring are inclined to each other by 10.55 (12)°, whereas the 4-methylbenzyl ring is nearly orthogonal to the pyridazine ring, with a dihedral angle of 72.97 (10)°. In the crystal, molecules are linked by pairs of O—H...O hydrogen bonds, forming inversion dimers with an R22(14) ring motif. The dimers are linked by C—H...O hydrogen bonds, generating ribbons propagating along the c-axis direction. The intermolecular interactions were additionally investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots. They revealed that the most significant contributions to the crystal packing are from H...H (48.4%), H...O/O...H (21.8%) and H...C/C...H (20.4%) contacts. Molecular orbital calculations providing electron-density plots of HOMO and LUMO molecular orbitals and molecular electrostatic potentials (MEP) were also computed, both with the DFT/B3LYP/6–311 G++(d,p) basis set.

In the title compound, C10H10N2OS, the five atoms of the thiophene ring are essentially coplanar (r.m.s. deviation = 0.0037 Å) and the pyridazine ring is non-planar. In the crystal, pairs of N—H...O hydrogen bonds link the molecules into dimers with an R22(8) ring motif. The dimers are linked by C—H...O interactions, forming layers parallel to the bc plane. The theoretical geometric parameters are in good agreement with XRD results. The intermolecular interactions were investigated using a Hirshfeld surface analysis and two-dimensional fingerprint plots. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are by H...H (39.7%), C...H/H...C (17.3%) and O...H/H...O (16.8%) contacts.

In the title compound, C13H14N2O3, the dihydropyridazine ring (r.m.s. deviation = 0.166 Å) has a screw-boat conformation. The dihedral angle between its mean plane and the benzene ring is 0.77 (12)°. In the crystal, intermolecular O—H...O hydrogen bonds generate C(5) chains and N—H...O hydrogen bonds produce R22(8) motifs. These types of interactions lead to the formation of layers parallel to (12\overline{1}). The three-dimensional network is achieved by C—H...O interactions, including R24(8) motifs. Intermolecular interactions were additionally investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots. The most significant contributions to the crystal packing are by H...H (43.3%), H...C/C...H (19.3%), H...O/H...O (22.6%), C...N/N...C (3.0%) and H...N/N...H (5.8%) contacts. C—H...π interactions and aromatic π–π stacking interactions are not observed.

The asymmetric units of the title compounds both contain one nonplanar molecule. In 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one, C17H14N2O, (I), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 46.69 (9)°; the phenyl ring of the benzyl group is nearly perpendicular to the plane of the pyridazine ring, the dihedral angle being 78.31 (10)°. In methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate, C20H16Cl2N2O3, (II), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 21.76 (18)°, whereas the phenyl ring of the dichlorobenzyl group is inclined to the pyridazine ring by 79.61 (19)°. In the crystal structure of (I), pairs of N—H...O hydrogen bonds link the molecules into inversion dimers with an R22(8) ring motif. In the crystal structure of (II), C—H...O hydrogen bonds generate dimers with R12(7), R22(16) and R22(18) ring motifs. The Hirshfeld surface analyses of compound (I) suggests that the most significant contributions to the crystal packing are by H...H (48.2%), C...H/H...C (29.9%) and O...H/H...O (8.9%) contacts. For compound (II), H...H (34.4%), C...H/H...C (21.3%) and O...H/H...O (16.5%) interactions are the most important contributions.

In the present work, we represent two thiazolidinediones, namely (Z)-5-(4-methoxybenzylidene) thiazolidine-2,4-dione (MeOTZD) and (Z)-5-(4-methylbenzylidene) thiazolidine-2,4-dione (MeTZD), as corrosion inhibitors for carbon steel (CS) in 1.0 M HCl solution. Techniques for gravimetric methods, electrochemical measurements, and morphological characterization were used to conduct experimental evaluations. Additionally, calculations based on the fundamental principles of Density Functional Theory (DFT) were employed to simulate inhibitor–iron interactions. Experimental results indicated that investigated inhibitors can significantly enhance the corrosion resistance of CS, reaching a performance of 95% and 87% at 5 × 10−3 mol/L of MeOTZ and MeTZD, respectively. According to gravimetric and electrochemical experiments, inhibitor molecules obstruct corrosion reactions by adhering to the CS surface, which follows the Langmuir isotherm model. On the other hand, the morphological analysis showed a well-distinguished difference between unprotected and protected CS surfaces as a result of the inhibitors’ addition to HCl. Projected density of states and interaction energies obtained from first-principles DFT simulations indicate that the studied molecules form covalent bonds with iron atoms through charge transfer.

In this paper, we describe the synthesis of a new dihydro-2H-pyridazin-3-one derivative. The molecule, C18H16N2O, is not planar; the benzene and pyridazine rings are twisted with respect to each other, making a dihedral angle of 11.47 (2)°, and the toluene ring is nearly perpendicular to the pyridazine ring, with a dihedral angle of 89.624 (1)°. The molecular conformation is stabilized by weak intramolecular C—H...N contacts. In the crystal, pairs of N—H...O hydrogen bonds link the molecules into inversion dimers with an R22(8) ring motif. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional (2D) fingerprint plots, revealing that the most important contributions for the crystal packing are from H...H (56.6%), H...C/C...H (22.6%), O...H/H...O (10.0%) and N...C/C...N (3.5%) interactions.

The title pyridazin-3(2H)-one derivative, C25H19FN2O2, crystallizes with two independent molecules (A and B) in the asymmetric unit. In molecule A, the 4-fluorophenyl ring, the benzyl ring and the phenyl ring are inclined to the central pyridazine ring by 86.54 (11), 3.70 (9) and 84.857 (13)°, respectively. In molecule B, the corresponding dihedral angles are 86.80 (9), 10.47 (8) and 82.01 (10)°, respectively. In the crystal, the A molecules are linked by pairs of C—H...F hydrogen bonds, forming inversion dimers with an R22(28) ring motif. The dimers are linked by C—H...O hydrogen bonds and a C—H...π interaction, forming columns stacking along the a-axis direction. The B molecules are linked to each other in a similar manner and form columns separating the columns of A molecules.

In the title quinoline derivative, C24H19NO3, the two benzyl rings are inclined to the quinoline ring mean plane by 74.09 (8) and 89.43 (7)°, and to each other by 63.97 (10)°. The carboxylate group is twisted from the quinoline ring mean plane by 32.2 (2)°. There is a short intramolecular C—H...O contact forming an S(6) ring motif. In the crystal, molecules are linked by bifurcated C—H,H...O hydrogen bonds, forming layers parallel to the ac plane. The layers are linked by C—H...π interactions, forming a supramolecular three-dimensional structure.

The title pyridazinone derivative, C21H19ClN2O3, is not planar. The unsubstituted phenyl ring and the pyridazine ring are inclined to each other, making a dihedral angle of 17.41 (13)° whereas the Cl-substituted phenyl ring is nearly orthogonal to the pyridazine ring [88.19 (13)°]. In the crystal, C—H...O hydrogen bonds generate dimers with R22(10) and R22(24) ring motifs which are linked by C—H...O interactions, forming chains extending parallel to the c-axis direction. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most significant contributions to the crystal packing are from H...H (44.5%), C...H/H...C (18.5%), H...O/H...O (15.6%), Cl...H/H...Cl (10.6%) and C...C (2.8%) contacts.

In the title quinoline derivative, C14H14ClNO3, there is an intramolecular C—H...O hydrogen bond forming an S(6) graph-set motif. The molecule is essentially planar with the mean plane of the ethyl acetate group making a dihedral angle of 5.02 (3)° with the ethyl 6-chloro-2-ethoxyquinoline mean plane. In the crystal, offset π–π interactions with a centroid-to-centroid distance of 3.4731 (14) Å link inversion-related molecules into columns along the c-axis direction. Hirshfeld surface analysis indicates that H...H contacts make the largest contribution (50.8%) to the Hirshfeld surface.

The asymmetric unit of the title compound, C17H12Cl2N2O, contains one independent molecule. The molecule is not planar, the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 29.96 (2)° and the dichlorophenyl ring is nearly perpendicular to the pyridazine ring, with a dihedral angle of 82.38 (11)°. In the crystal, pairs of N—H...O hydrogen bonds link the molecules to form inversion dimers with an R22(8) ring motif. The dimers are linked by C—H...O interactions, forming layers parallel to the bc plane. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, and the molecular electrostatic potential surface was also analysed. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are by H...H (31.4%), Cl...H/H...Cl (19.9%) and C...H/H...C (19%) contacts.

The asymmetric unit of the title compound, C20H20N4O·0.5H2O, contains two independent organic molecules (1 and 2) and a water molecule of crystallization. The two molecules differ primarily in the dihedral angles between the aromatic rings, which are 7.79 (7) and 29.89 (7)° in molecules 1 and 2, respectively. In each molecule there is intramolecular C—H...O hydrogen bond forming an S(6) ring motif. In molecule 1 there is an intramolecular N—H...π(pyrazole) interaction and an intramolecular C—H...π(pyrazole) interaction present. Molecule 1 is linked to molecule 2 by a C—H...π(benzene ring) interaction. An intramolecular N—H...N hydrogen bond and an intramolecular C—H...N hydrogen bond are also present in molecule 2. In the crystal, the three components are linked by Owater—H...N, N—H...Owater and N—H...N hydrogen bonds, forming chains along the [100] direction. The chains are linked by C—H...O and C—H...N hydrogen bonds, forming layers parallel to the ab plane. Finally, the layers are linked by C—H...π interactions, forming a three-dimensional structure.

In the title compound, C10H8Cl2N2O, the seven-membered diazepine ring adopts a boat-shaped conformation. The mean planes of the two rings of the benzodiazepine unit are inclined to each other by 22.05 (6)°. In the crystal, molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers with an R22(8) ring motif. The dimers are linked by C—H...π interactions, forming layers lying parallel to (10\overline{1}). The roles of the intermolecular interactions in the crystal packing were clarified using Hirshfeld surface analysis; the most important contributions are from Cl...H/H...Cl (30.5%) and H...H (22.5%) interactions.

Abstract Background Nowadays, is emerging a new generation of highly promising inhibitors bearing the β-ketoenol functionality. The present work relates to the first synthesis, the structure determination, the DFT studies and the use of a new biomolecule designed with a β-ketoenol group bounded to a pyrazolic moiety. Result A novel β-ketoenol-pyrazole has been synthesized, well characterized and its structure was confirmed by single crystal X-ray diffraction. The electron densities and the HOMO–LUMO gap have been calculated using the DFT method with BLYP, PW91, PWC functionals and 6-31G* basis set. An evaluation of the molecule stability is provided by a NBO analysis and the calculated Fukui and Parr functions have been used to locate the reactive electrophile and nucleophile centers in the molecule. The synthesized compound, screened for its in vitro antifungal behavior against the Fusarium oxysporum f.sp. albedinis FAO fungal strains, shows a moderate activity with an inhibition percentage of 46%. The product was also tested against three bacterial strains (Escherichia coli, Bacillus subtilis and Micrococcus luteus), but no significant effect was observed against these organisms. Conclusions Density functional calculations are used to evaluate the HOMO–LUMO energy gap, the molecular electrostatic potential and to provide a natural bond orbital analysis. The measured antimicrobial activities encourage us to continue searching for other structures, likely to be good antifungal candidates.

The present study was conducted to evaluate a natural extract, obtained from the Beta vulgaris plant, for its phytochemical composition and its beneficial health effects. Therefore, total phenolic and flavonoid contents, as well as identification and quantification of phenolic compounds by HPLC, were assessed in leaves’ extract. Moreover, antioxidant activities were investigated using free radical scavenging tests, (ABTS+ and DPPH+) and reducing power assay (FRAP) as well as ferrous ions’ (Fe2+) chelating activity. The Antiglycation effect was also evaluated, using the BSA-fructose model, and the antidiabetic effect was determined by inhibition of α-amylase and α-glucosidase enzymes. Additionally, the in vitro antitumor effect was quantified using the MTT assay, and the antibacterial activity was evaluated using the agar disc diffusion and broth microdilution methods. Both aqueous and methanolic extracts exhibited potential antioxidant capacity with a higher effect for the methanolic extract. Furthermore, the in vitro antitumor activity of the methanolic extracts exhibited potent cytotoxic effects against two breast cancer cell lines, MDA-MB-468 and MCF-7. Moreover, Beta vulgaris extracts inhibit not only α-amylase and α-glucosidase, but also advanced glycation end-products’ (AGEs) formation, which would prevent diabetes’ complications. Beta vulgaris methanolic extract revealed also a high antibacterial effect against Proteus mirabilis and Bacillus subtilis. Taken together, these results revealed that Beta vulgaris leaves’ extracts constitute a valuable food and natural source of bioactive molecules that could be used for the development of new, natural drugs against cancer and diabetes.

Copper is the third-most-produced metal globally due to its exceptional mechanical and thermal properties, among others. However, it suffers serious dissolution issues when exposed to corrosive mediums. Herein, two thiazolidinedione derivatives, namely, (Z)-5-(4-methylbenzylidene)thiazolidine-2,4-dione (MTZD) and (Z)-3-allyl-5-(4-methylbenzylidene)thiazolidine-2,4-dione (ATZD), were synthesized and applied for corrosion protection of copper in 3.5 wt.% NaCl medium. The corrosion inhibition performance of tested compounds was evaluated at different experimental conditions using electrochemical impedance spectroscopy (EIS), potentiodynamic polarization curves (PPC) and atomic force microscopy (AFM). EIS results revealed that the addition of studied inhibitors limited the dissolution of copper in NaCl solution, leading to a high polarization resistance compared with the blank solution. In addition, PPC suggested that tested compounds had a mixed-type effect, decreasing anodic and cathodic corrosion reactions. Moreover, surface characterization by AFM indicated a significant decrease in surface roughness of copper after the addition of inhibitors. Outcomes from the present study suggest that ATZD (IE% = 96%) outperforms MTZD (IE% = 90%) slightly, due to the presence of additional –C3H5 unit (–CH2–CH = CH2) in the molecular scaffold of MTZD.

In order to evaluate the antioxidant properties of aqueous and methanol extracts of needles and berries of Juniperus oxycedrus subsp. oxycedrus (Joo) species, various antioxidant capacity assessment tests (free radical scavenging assays (DPPH• and ABTS•+ tests), ferrous ions (Fe2+) chelating activity and reducing power assay (FRAP) were conducted. In all of the tests, the extracts exhibited strong antioxidant activity. Furthermore, in-vitro cytotoxic activity assays of the methanolic extracts showed potent cytotoxic effects against two breast cancer cell lines (MDA-MB-468 and MCF-7), with no cytotoxicity towards normal cells (PBMCs). Reactive oxygen species generation was presumed to be a potential reason for the observed cytotoxic effects. According to all the above, and considering its appropriate composition of mineral elements and phenolic compounds, Joo could offer a beneficial and natural source of bioactive compounds that can be either used on the preventive side as it could potentially be used in the clinic without toxicity.

In the title compound, C15H15NO5S, the benzene and heterocyclic rings are close to being coplanar [dihedral angle = 1.49 (6)°]. In the crystal, pairwise C—H...O hydrogen bonds form dimers, which are arranged into `stair-step' rows by way of C=O–π interactions between a carbonyl group and the benzene ring [O...π = 3.3837 (12) Å].

In the title compound, C17H13BrN4O, the dihedral angles between the pyrazole ring and the pedant phenyl and bromobenzene rings are 21.61 (11) and 28.09 (11)°, respectively. In the crystal, N—H...O hydrogen bonds link the molecules into [010] chains, which are reinforced by C—H...O interactions.

The title 1-H-pyrazole-3-carbohydrazide molecule, C13H14N4O, shows a slight twist from end to end. The packing features N—H...N and bifurcated N—H...(N,O) hydrogen bonds, which generate (010) sheets.

In the title compound, C18H16N4O, the planes of the phenyl rings are approximately perpendicular to each other [dihedral angle = 78.07 (8)°] and form dihedral angles of 56.43 (8) and 24.59 (8)° with the pyrazole ring. In the crystal, molecules are linked by N—H...O hydrogen bonds to form one-dimensional chains parallel to the [010] direction.

Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. The presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antipsychotic CDPPB, the anti-obesity drug rimonabant, difenamizole, an analgesic, betazole, a H2-receptor agonist and the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Owing to this diversity in the biological field, this nucleus has attracted the attention of many researchers to study its skeleton chemically and biologically. This review highlights the different synthesis methods and the pharmacological properties of pyrazole derivatives. Studies on the synthesis and biological activity of pyrazole derivatives developed by many scientists around the globe are reported.

The development of low-cost catalytic systems that mimic the activity of tyrosinase enzymes (Catechol oxidase) is of great promise for future biochemistry technologic demands. Herein, we report the synthesis of new biomolecules systems based on hydrazone derivatives containing a pyrazole moiety (L1–L6) with superior catecholase activity. Crystal structures of L1 and L2 biomolecules were determined by X-ray single crystal diffraction (XRD). Optimized geometrical parameters were calculated by density functional theory (DFT) at B3LYP/6–31G (d, p) level and were found to be in good agreement with single crystal XRD data. Copper (II) complexes of the compounds (L1–L6), generated in-situ, were investigated for their catalytic activities towards the oxidation reaction of catechol to ortho-quinone with the atmospheric dioxygen, in an attempt to model the activity of the copper containing enzyme tyrosinase. The studies showed that the activities depend on four parameters: the nature of the ligand, the nature of counter anion, the nature of solvent and the concentration of ligand. The Cu(II)-ligands, given here, present the highest catalytic activity (72.920 μmol·L−1·min−1) among the catalysts recently reported in the existing literature.

Quinoxalinone and its derivatives are used in organic synthesis for building natural and designed synthetic compounds and they have been frequently utilized as suitable skeletons for the design of biologically active compound. This review covers updated information on the most active quinoxalinone derivatives that have been reported to show considerable pharmacological actions such as antimicrobial, anti-inflammatory, antidiabetic, antiviral, antitumor, and antitubercular activity. It can act as an important tool for chemists to develop newer quinoxalinone derivatives that may prove to be better agents in terms of efficacy and safety.

The molecule of the title compound, C42H32N6O, is built up from one pyrazole ring linked to three phenyl rings and to an approximately planar [maximum deviation = 0.0455 (15) Å] quinoxaline system connected to a phenylbenzohydrazide group. The pyrazole ring assumes an envelope conformation, the C atom attached to the quinoxalin-3-yl ring system being the flap atom. The dihedral angle between the two phenyl rings of the phenylbenzohydrazide group is of 58.27 (9)°. The mean plane through the pyrazole ring is nearly perpendicular to the quinoxaline ring system and to the phenyl ring attached to the opposite side, forming dihedral angles of 82.58 (7) and 87.29 (9)°, respectively. An intramolecular C—H...O hydrogen bond is present. In the crystal, molecules are linked by pairs of N—H...N hydrogen bonds, forming inversion dimers, which are further connected by C—H...N hydrogen bonds into chains parallel to the b axis.