Search

In light of the increasing antibiotic resistance, it is crucial to discover new antimicrobial medications. Pyridazines are frequently investigated in research for the development of new chemical entities with enhanced therapeutic properties. Their structure allows for significant flexibility in the attachment of various functional groups, which is essential for drug discovery.Our work focuses on synthesizing new pyridazine derivatives (7a, 7b, 7c and 7d) through coupling reactions with various amino esters. The structures of these compounds have been analyzed using spectroscopic measurements including 1H, 13C NMR, IR, and mass spectroscopy. The compounds showed positive effects against two bacterial strains: Escherichia coli: ATCC25922 and Staphylococcus aureus: CIP543154. Molecular docking results of the protein 7AZ5 indicated significant affinities with these molecules through hydrogen bonds. Compounds 7a and 7d demonstrated the highest binding energies and the best antimicrobial activity, suggesting their potential as a model for creating novel and potent antimicrobial compounds.

In the title molecule, C21H23N3O3, the imidazolidine ring slightly deviates from planarity and the morpholine ring exhibits the chair conformation. In the crystal, N—H...O and C—H...O hydrogen bonds form helical chains of molecules extending parallel to the c axis that are connected by C—H...π(ring) interactions. A Hirshfeld surface analysis reveals that the most important contributions for the crystal packing are from H...H (55.2%), H...C/C...H (22.6%) and H...O/O...H (20.5%) interactions. The volume of the crystal voids and the percentage of free space were calculated to be 236.78 Å3 and 12.71%, respectively. Evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization is dominated by the nearly equal electrostatic and dispersion energy contributions. The DFT-optimized molecular structure at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state. Moreover, the HOMO–LUMO behaviour was elucidated to determine the energy gap.

The aim of the present study is to analyze the phenolic compounds extracted from seeds of four spices belonging to Apiaceae family, namely caraway (Carum carvi), coriander (Coriandrum sativum L.), mystical cumin (Ammodaucus leucotrichus), and cumin (Cuminum cyminum L.). The extraction was carried out using solvents of different polarities (water, ethanol, methanol, and hexane). The antioxidant activity of each studied spice was performed by different methods including total antioxidant capacity (TAC), 2,2'-azino-bis3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 1,1-diphenyl-2 picrylhydrazyl (DPPH), ferric reducing antioxidant power (FRAP), and metal ion chelation power (CP). Based on obtained results, a significant difference in the phenolic compounds contents of analyzed seeds was observed. The lowest phenolic compounds level was obtained by the hexane extract for the four studied spices. Besides, the aqueous extract (AE) of conventional cumin showed the highest level of phenolic compounds (16.49 mg Gallic acid equivalents (GAE)/g dry weight (DW)), followed by the AE of caraway (15.9 mg GAE/g DW), then the AE of mystical cumin (15.01 mg GAE/DW), and, at the end, by the AE of coriander (12.89 mg GAE/g DW). This work revealed a well correlation between the antioxidant activities of the studied seed and the type of solvents used for their extraction. The studied spices present a much-diversified molecular weights distribution of the phenolic compounds evaluated by exclusion chromatography on Sephadex G50 gel. The climatological analysis showed also that the production of phenolic compounds was strongly influenced by some environmental factors such as the mean annual rainfall and temperature values registered in the planting zones of the four studied spices in Morocco.

The indoline portion of the title molecule, C16H13NO2, is planar. In the crystal, a layer structure is generated by C—H...O hydrogen bonds and C—H...π(ring), π-stacking and C=O...π(ring) interactions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (43.0%), H...C/C...H (25.0%) and H...O/O...H (22.8%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. The volume of the crystal voids and the percentage of free space were calculated to be 120.52 Å3 and 9.64%, respectively, showing that there is no large cavity in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the stabilization is dominated by the dispersion energy contributions in the title compound. Moreover, the DFT-optimized structure at the B3LYP/6-311G(d,p) level is compared with the experimentally determined molecular structure in the solid state.

In the title molecule, C7H7N3O, the pyrimidine ring is essentially planar, with the propynyl group rotated out of this plane by 15.31 (4)°. In the crystal, a tri-periodic network is formed by N—H...O, N—H...N and C—H...O hydrogen-bonding and slipped π–π stacking interactions, leading to narrow channels extending parallel to the c axis. Hirshfeld surface analysis of the crystal structure reveals that the most important contributions for the crystal packing are from H...H (36.2%), H...C/C...H (20.9%), H...O/O...H (17.8%) and H...N/N...H (12.2%) interactions, showing that hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization is dominated by the electrostatic energy contributions. The molecular structure optimized by density functional theory (DFT) calculations at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The HOMO–LUMO behaviour was also elucidated to determine the energy gap.

In the title compound, C20H28BrNO2, the indoline portion is almost planar and the 12-bromododecyl chain adopts an all-trans conformation apart from the gauche terminal C—C—C—Br fragment. A micellar-like structure is generated in the crystal by C—H...O hydrogen bonds and π-stacking interactions between indolinedione head groups and intercalation of the 12-bromododecyl tails. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (58.9%), H...O/O...H (17.9%) and H...Br/Br...H (9.5%) contacts. A density functional theory (DFT) optimized structure at the B3LYP/ 6–311 G(d,p) level shows good agreement with the experimentally determined molecular structure in the solid state.

The asymmetric unit of the title compound, C12H13N3O4, consists of two molecules differing to a small degree in their conformations. In the crystal, layers of molecules are connected by weak C—H...O hydrogen bonds and slipped π-stacking interactions. These layers lie parallel to (10\overline{1}) and are stacked along the normal to that plane. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing arise from H...H (43.5%) and H...O/O...H (30.8%) contacts. The density functional theory (DFT) optimized structure of the title compound at the B3LYP/ 6–311 G(d,p) level agrees well with the experimentally determined molecular structure in the solid state.

In the title molecule, C14H11NO3, the dihydroquinoline core deviates slightly from planarity, indicated by the dihedral angle of 1.07 (3)° between the two six-membered rings. In the crystal, layers of molecules almost parallel to the bc plane are formed by C—H...O hydrogen bonds. These are joined by π–π stacking interactions. A Hirshfeld surface analysis revealed that the most important contributions to the crystal packing are from H...H (36.0%), H...C/C...H (28.9%) and H...O/O...H (23.5%) interactions. The evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization is dominated by the dispersion energy contribution. Moreover, the molecular structure optimized by density functional theory (DFT) at the B3LYP/6-311G(d,p) level is compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

Coriander, caraway, and mystical cumin are famous for their aromatic properties and widely used in Moroccan cuisine. The nutritional/phytochemical composition of their seeds (used for food flavoring and preservation) were compared. Their antioxidant, anti-inflammatory, cytotoxic and hepatotoxic effects were also explored. The fat content was similar among the samples (13%), with monounsaturated fatty acids being predominant. The coriander and mystical cumin seeds were extremely rich in C18:1n9c (81 and 85%, respectively) while, in the caraway, C18:1n12 (25%) was found together with C18:1n9c (32%). The caraway seeds also presented a higher proportion of C18:2n6c (34%) than the other seeds (13 and 8%, correspondingly). γ-Tocotrienol was the major vitamin E form in all the samples. The caraway seeds contained double the amount of protein (~18%) compared to the other seeds (~8%) but, qualitatively, the amino acid profiles among all seeds were similar. The seeds were also rich in dietary fiber (40–53%); however, differences were found in their fiber profiles. Caraway showed the highest antioxidant profile and anti-inflammatory activity and an LC-DAD-ESI/MSn analysis revealed great differences in the phenolic profiles of the samples. Cytotoxicity (NCI-H460, AGS, MCF-7, and CaCo2) and hepatotoxicity (RAW 264.7) were not observed. In sum, besides their flavoring/preservation properties, these seeds are also relevant source of bioactive compounds with health-promoting activities.

The development of novel antimicrobial drugs is crucial due to the increasing problem of antibiotic resistance. A new series of 1,4-disubstituted-1,2,3-triazole derivatives containing a cytosine moiety (3a, 3b, 3c and 3d) were synthesized using 1,3-dipolar cycloaddition in a mixture of ethanol and water under Cu(I)-catalyzed with N-alkyl: 1-(prop-2-ynyl)-4-amino-2-oxopyrimidine 2 as dipolarophiles and azide derivatives (sucre-azoture) as dipoles. The desired products were obtained in good yields by reacting with a catalytic amount of copper (II) sulfate and sodium ascorbate. The structure of these compounds was analyzed and characterized using spectroscopic measurements such as 1H NMR, 13C NMR, and mass spectroscopy. Encouragingly, all cycloaddition molecules exhibited promising activity against various bacterial strains including Staphylococcus aureus and Escherichia coli. The crystal structure modeling of protein 7AZ5 demonstrated strong binding affinities through hydrogen bonds with these molecules. The cycloaddition compounds displayed the highest binding energies in terms of antimicrobial efficacy. This suggests that these substances could serve as an effective model for the development and production of new and potent antimicrobial agents.

Ten new isatin derivatives (2–11) were synthesized by alkylation reactions under phase transfer catalysis (PTC) conditions. Structural characterization of all compounds was performed using 1H and 13C NMR spectroscopy. The molecular and crystal structures of three compounds (4, 7, and 8) were confirmed through single-crystal X-ray diffraction analysis. Spectral data were also calculated using density function theory (DFT) at the B3LYP/6–311++G(d, p) level and compared to the experimental results, to understand the non-binding intermolecular interactions in the solid phase crystal packing. The closest contacts between atoms of the three molecules studied were identified by 2D and 3D Hirshfeld surface analyses. The structures of 4, 7 and 8 are optimized and their HOMO and LUMO energies, as well as their orbital pictures were evaluated. The experimental results correlated well with the calculated results. Finally, molecular docking studies of 4, 7 and 8 were performed to investigate their binding patterns with inhibitory targets from the Protein Data Bank (PDB: 3G7B and PDB: 3T0T using the AutoDock Vina program. The antibacterial activities of 2–11 against Gram-positive and Gram-negative microbial strains, such as Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa were evaluated, and the findings indicated that 4 and 8 exhibited the highest efficacy, as reflected in their minimal inhibitory concentration (MIC) values.

As they facilitate the cleavage of single and double stranded DNA to relax supercoils, unwind catenanes, and condense chromosomes in eukaryotic cells, Topoisomerase plays crucial roles in cellular reproduction and DNA organization. Because the unrepaired single and double stranded DNA breaks these complexes generate might result in apoptosis and cell death, they are cytotoxic agents.In this study, 28 compounds derived from phosphorus-substituted quinoline are subjected to a quantitative structure–activity relationship (QSAR) using partial least squares, principal component regression, and multiple linear regression. The Gaussian 09 software and the Molecular Operating Environment program were used to calculate molecular descriptors. The anti-proliferative activity was correlated with a variety of electronic and structural characteristics of the molecules, such as EHOMO (energy of the highest occupied molecular orbital) and ELUMO (energy of the lowest unoccupied molecular orbital), which provided evidence for the modeling. The B3LYP/6-31G (d, p) level of theory's Density Functional Theory (DFT) approach was used to compute these electronic properties, and Principal Component Analysis (PCA) was used to test for collinearity between the descriptors. In fact, three alternative prediction models were created using various 2D and 3D descriptor counts, and they were each assessed using the statistical metrics of coefficient of determination (R2) and root mean squared error (RMSE). A MLR model had the best predictive performance of all the constructed models, as indicated by R2 and RMSE of 0.865 and 0.316, respectively.Three proteins (6G77, 2NS2, and 5K47) for lung, ovarian, and kidney malignancies showed strong binding affinities via hydrophobic interactions and H-bonds with the pertinent chemicals by crystal structure modeling. Compounds C11, C19 and C26, respectively, showed the highest binding energy for ovarian, kidney and lung cancer. The outcomes of the molecular dynamic MD simulation diagram were produced to support the molecular docking findings from earlier research, which demonstrated that inhibitors were stable in the active sites of the selected proteins for 10 ns. This raises the possibility that these chemicals could serve as a valuable model for the development and synthesis of more effective anticancer prospects.

In the title compound, C12H10ClNO3, the dihydroquinoline moiety is not planar with a dihedral angle between the two ring planes of 1.61 (6)°. An intramolecular C—H...O hydrogen bond helps to establish the rotational orientation of the carboxyl group. In the crystal, sheets of molecules parallel to (10\overline{1}) are generated by C—H...O and C—H...Cl hydrogen bonds, and are stacked through slipped π-stacking interactions between inversion-related dihydroquinoline units. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (34.2%), H...O/O...H (19.9%), H...Cl/Cl...H (12.8%), H...C/C...H (10.3%) and C...C (9.7%) interactions. Computational chemistry indicates that in the crystal, the C—H...Cl hydrogen-bond energy is −37.4 kJ mol−1, while the C—H...O hydrogen-bond energies are −45.4 and −29.2 kJ mol−1. An evaluation of the electrostatic, dispersion and total energy frameworks revealed that the stabilization is dominated via the dispersion energy contribution. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state, and the HOMO—LUMO behaviour was elucidated to determine the energy gap.

5-bromopyridine-2,3-diamine reacted with benzaldehyde to afford the corresponding 6-Bromo-2-phenyl-3H-imidazo[4,5-b]pyridine (1). The reaction of the latter compound (1) with a series of halogenated derivatives under conditions of phase transfer catalysis solid–liquid (CTP) allows the isolation of the expected regioisomers compounds (2–8). The alkylation reaction of (1) gives, each time, two regioisomers, N3 and N4; in the case of ethyl bromoactate, the reaction gives, at the same time, the three N1, N3 and N4 regioisomers. The structures of synthesized compounds were elucidated on the basis of different spectral data (1H NMR, 13C NMR), X-Ray diffraction and theoretical study using the DFT method, and confirmed for each compound. Hirshfeld surface analysis was used to determine the intermolecular interactions responsible for the stabilization of the molecule. Density functional theory was used to optimize the compounds, and the HOMO-LUMO energy gap was calculated, which was used to examine the inter/intra molecular charge transfer. The molecular electrostatic potential map was calculated to investigate the reactive sites that were present in the molecule. In order to determine the potential mode of interactions with DHFR active sites, the three N1, N3 and N4 regioisomers were further subjected to molecular docking study. The results confirmed that these analogs adopted numerous important interactions, with the amino acid of the enzyme being targeted. Thus, the most docking efficient molecules, 2 and 4, were tested in vitro for their antibacterial activity against Gram-positive bacteria (Bacillus cereus) and Gram-negative bacteria (Escherichia coli). Gram-positive bacteria were more sensitive to the action of these compounds compared to the Gram-negative, which were much more resistant.

In the title molecule, C20H24Br2N4, the imidazopyridine moiety is not planar as indicated by the dihedral angle of 2.0 (2)° between the constituent rings; the 4-dimethylaminophenyl ring is inclined to the mean plane of the imidazole ring by 27.4 (1)°. In the crystal, two sets of C—H...π(ring) interactions form stacks of molecules extending parallel to the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (42.2%), H...C/C...H (23.1%) and H...Br/Br...H (22.3%) interactions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO–LUMO energy gap is 2.3591 eV.

The title quinoxaline molecule, C23H20N2O2, is not planar, the dihedral angle angle between the mean planes of the benzene rings being 72.54 (15)°. In the crystal, molecules are connected into chains extending parallel to (10\overline{1}) by weak C—H...O hydrogen bonds. Weak C—H...π interactions link the chains, forming a three-dimensional network structure. Hirshfeld surface analysis revealed that the most important contributions for the crystal packing are from H...H (48.7%), H...C/C...H (32.0%), H...O/O...H (15.4%), C...C (1.9%), H...N/N...H (1.1%) contacts.

The title compound, C24H30Br2N4O2, consists of a 2-(4-nitrophenyl)-4H-imidazo[4,5-b]pyridine entity with a 12-bromododecyl substituent attached to the pyridine N atom. The middle eight-carbon portion of the side chain is planar to within 0.09 (1) Å and makes a dihedral angle of 21.9 (8)° with the mean plane of the imidazolopyridine moiety, giving the molecule a V-shape. In the crystal, the imidazolopyridine units are associated through slipped π–π stacking interactions together with weak C—HPyr...ONtr and C—HBrmdcyl...ONtr (Pyr = pyridine, Ntr = nitro and Brmdcyl = bromododecyl) hydrogen bonds. The 12-bromododecyl chains overlap with each other between the stacks. The terminal –CH2Br group of the side chain shows disorder over two resolved sites in a 0.902 (3):0.098 (3) ratio. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (48.1%), H...Br/Br...H (15.0%) and H...O/O...H (12.8%) interactions. The optimized molecular structure, using density functional theory at the B3LYP/ 6–311 G(d,p) level, is compared with the experimentally determined structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

The title compound, C24H24N2O6, consists of ethyl 2-(1,2,3,4-tetrahydro-2-oxoquinolin-1-yl)acetate and 4-[(2-ethoxy-2-oxoethyl)(phenyl)carbomoyl] units, where the oxoquinoline unit is almost planar and the acetate substituent is nearly perpendicular to its mean plane. In the crystal, C—HOxqn...OEthx and C—HPhyl...OCarbx (Oxqn = oxoquinolin, Ethx = ethoxy, Phyl = phenyl and Carbx = carboxylate) weak hydrogen bonds link the molecules into a three-dimensional network sturucture. A π–π interaction between the constituent rings of the oxoquinoline unit, with a centroid–centroid distance of 3.675 (1) Å may further stabilize the structure. Both terminal ethyl groups are disordered over two sets of sites. The ratios of the refined occupanies are 0.821 (8):0.179 (8) and 0.651 (18):0.349 (18). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (53.9%), H...O/O...H (28.5%) and H...C/C...H (11.8%) interactions. Weak intermolecular hydrogen-bond interactions and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) geometric optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO molecular orbital behaviour was elucidated to determine the energy gap.

The title compound, C15H12ClNO3, consists of a 1,2-dihydroquinoline-4-carboxylate unit with 2-chloroethyl and propynyl substituents, where the quinoline moiety is almost planar and the propynyl substituent is nearly perpendicular to its mean plane. In the crystal, the molecules form zigzag stacks along the a-axis direction through slightly offset π-stacking interactions between inversion-related quinoline moieties which are tied together by intermolecular C—HPrpnyl...OCarbx and C—HChlethy...OCarbx (Prpnyl = propynyl, Carbx = carboxylate and Chlethy = chloroethyl) hydrogen bonds. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (29.9%), H...O/O...H (21.4%), H...C/C... H (19.4%), H...Cl/Cl...H (16.3%) and C...C (8.6%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the C—HPrpnyl...OCarbx and C—HChlethy...OCarbx hydrogen bond energies are 67.1 and 61.7 kJ mol−1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/ 6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

The title compound, C14H15BrClNO4, consists of a 5-bromoindoline-2,3-dione unit linked to a 1-{2-[2-(2-chloroethoxy)ethoxy]ethyl} moiety. In the crystal, a series of C—H...O hydrogen bonds link the molecules to form a supramolecular three-dimensional structure, enclosing R22(8), R22(12), R22(18) and R22(22) ring motifs. π–π contacts between the five-membered dione rings may further stabilize the structure, with a centroid–centroid distance of 3.899 (2) Å. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (28.1%), H...O/O...H (23.5%), H...Br/Br...H (13.8%), H...Cl/Cl...H (13.0%) and H...C/C...H (10.2%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO—LUMO behaviour was elucidated to determine the energy gap. The chloroethoxyethoxyethyl side chain atoms are disordered over two sets of sites with an occupancy ratio of 0.665 (8):0.335 (6).

The title compound, C21H16N2O2, consists of an imidazolidine unit linked to two phenyl rings and two prop-2-yn-1-yl moieties. The imidazolidine ring is oriented at dihedral angles of 79.10 (5) and 82.61 (5)° with respect to the phenyl rings, while the dihedral angle between the two phenyl rings is 62.06 (5)°. In the crystal, intermolecular C—HProp...OImdzln (Prop = prop-2-yn-1-yl and Imdzln = imidazolidine) hydrogen bonds link the molecules into infinite chains along the b-axis direction. Two weak C—HPhen...π interactions are also observed. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (43.3%), H...C/C...H (37.8%) and H...O/O...H (18.0%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that the C—HProp...OImdzln hydrogen-bond energy in the crystal is −40.7 kJ mol−1. Density functional theory (DFT) optimized structures at the B3LYP/6–311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

The title compound, C15H11BrClN3, is built up from a planar imidazo[4,5-b]pyridine unit linked to phenyl and allyl substituents. The allyl substituent is rotated significantly out of the imidazo[4,5-b]pyridine plane, while the benzene ring is inclined by 3.84 (6)° to the ring system. In the crystal, molecules are linked via a pair of weak intermolecular C—H...N hydrogen bonds, forming an inversion dimer with an R22(20) ring motif. The dimers are further connected by π–π stacking interactions between the imidazo[4,5-b]pyridine ring systems [centroid–centroid distances = 3.7161 (13) and 3.8478 (13) Å]. The important contributions to the Hirshfeld surface are H...H (35.9%), H...Cl/Cl...H (15.0%), H...C/C...H (12.4%), H...Br/Br...H (10.8%), H...N/N...H (7.5%), C...Br/Br...C (5.9%), C...C (5.5%) and C...N/N...C (4.0%) contacts.

Pomegranate variety properties are important not only to demonstrate their diversity but also to satisfy the current market need for high-quality fruits. This study aims to characterize pomological and physico-chemical features as well as the antioxidant capacity of Moroccan local cultivars (Djeibi, Mersi, Sefri 1 and Sefri 2) compared to the imported ones (Mollar de Elche and Hicaz). The pomological characteristics of varieties were relatively diverse. The juice varieties (PJ) displayed a marketed variability in organoleptic and quality properties, such as the flavor, juice yield, and micro/macronutrients contents. Interrelationships among the analyzed properties and PJ varieties were investigated by principal component analysis (PCA). Dimension of the data set was reduced to two components by PCA accounting for 64.53% of the variability observed. The rinds varieties (PR) were studied for their total phenolics, flavonoids, and condensed tannins quantifications. PR varieties extracts exhibited different levels of free radical scavenging activity and local varieties revealed a greater potential with stability over time. The HPLC-DAD analyses of PR extracts revealed (+) catechin as the major compound, where the highest content was found for the local varieties. The SEC analysis showed the molecular weight distribution of phenolic compounds with a high size of condensed tannins formed by the polymerization of the catechin monomer. Given these properties, this research provides an easy selection of high-quality fruits as potential candidates for local market needs.

In the title compound, C23H26BrClN6, the imidazo[4,5-b]pyridine ring system (r.m.s. deviation = 0.012 Å) is inclined at angles of 19.37 (12) and 89.27 (13)° to the phenyl and triazole rings, respectively, while the phenyl and triazole rings subtend a dihedral angle of 71.23 (15)°. In the crystal, the molecules are linked by C—H...NI and bifurcated C—H...(NT,NT) (I = imidazo[4,5-b]pyridine and T = triazole) hydrogen bonds into a double-column structure propagating along the b-axis direction.

Snails were fed with three medicinal plants belonging to the Lamiaceae family (rosemary, sage, and peppermint) in order to test their effects on those animals with high nutritive values. The media of raising were flour containing different percentages of the cited plants ranging from 1% to 9%. The feed had benefits on the raised snails depending on the plant and its percentage. Minerals in those aromatic plants, especially zinc and magnesium, had their effect on protein synthesis in snails fed with those plant percentages. Rosemary was the most profitable plant with the highest protein amount, the lowest mortality rate, and reduced microbial charge. Furthermore, it was a good regulator of the specific catalase activity which confirmed the role of the antioxidant activity of rosemary during raising snails.

A new series of amino acid derivatives of quinolines was synthesized through the hydrolysis of amino acid methyl esters of quinoline carboxamides with alkali hydroxide. The compounds were purified on silica gel by column chromatography and further characterized by TLC, NMR and ESI-TOF mass spectrometry. All compounds were screened for in vitro antimicrobial activity against different bacterial strains using the microdilution method. Most of the synthesized amino acid-quinolines show more potent or equipotent inhibitory action against the tested bacteria than their correspond esters. In addition, many of them exhibit fluorescent properties and could possibly be utilized as fluorophores. Molecular docking and simulation studies of the compounds at putative bacterial target enzymes suggest that the antimicrobial potency of these synthesized analogues could be due to enzyme inhibition via their favorable binding at the fluoroquinolone binding site at the GyrA subunit of DNA gyrase and/or the ParC subunit of topoisomerase-IV.

In the central dihydroquinoline unit of the title compound, C22H16BrN3O3, the dihydropyridinone and benzene rings are inclined to one another by 2.0 (1)°, while the outer pyridine rings are almost perpendicular to the plane of the dihydroquinoline ring system. The conformation of the molecule is partially determined by an intramolecular C—H...O hydrogen bond. In the crystal, molecules stack along the b-axis direction through a combination of C—H...N and C—H...O hydrogen bonds and π–π stacking interactions involving the dihydroquinoline units, with a centroid-to-centroid distance of 3.7648 (15) Å.

In the title compound, C13H8BrN3O2, the pyrido-pyrazine fused-ring system is essentially planar (r.m.s. deviation = 0.061 Å). The prop-2-ynyl moieties are twisted away from the ring system in opposite directions. In the crystal, a single weak C—H...O interaction generates [010] chains and aromatic π–π stacking interactions between the pyridine rings are observed.

The title compound, C21H18N4O2, crystallizes with one independent molecule in the asymmetric unit. The 6-methylquinoxaline-2,3(1H,4H)-dione unit is essentially planar. The dihedral angles between the mean plane of the 6-methylquinoxaline-2,3(1H,4H)-dione ring and its pendant pyridin-2-yl rings are 85.1 (3) and 73.8 (4)°. The pyridin-2-yl rings are inclined pointing away from the 6-methylquinoxaline-2,3(1H,4H)-dione ring system. In the crystal, molecules are linked by weak C—H...O interactions, forming a three-dimensional network structure.

In the title compound, C23H20N2S2, the mean planes of the phenyl rings are twisted with respect to the mean plane of the quinoxaline ring system by 73.8 (8) and 72.2 (8)°. A weak intramolecular C—H...N interactions is observed. The methyl group attached to the quinoxaline ring system is disordered over two sets of sites on the benzene ring having occupancies 0.531 (7) and 0.469 (7), respectively. One of the phenyl rings is disordered over two sets of sites having occupancies 0.649 (7) and 0.351 (10), respectively. In the crystal, π–π stacking interactions occur.

The title compound, C22H17ClN2O2, crystallizes with two independent molecules (A and B) in the asymmetric unit. The 6-chloroquinoxaline-2,3(1H,4H)-dione ring system is essentially planar. The dihedral angles between the mean planes of the 6-chloroquinoxaline-2,3(1H,4H)-dione ring and the phenyl rings of the benzyl substituents in the two molecules are 68.34 and 73.8 (7)° for A, and 73.8 (5) and 80.7 (1)° for B, so that these rings point away from the quinoxaline ring system. In the crystal, weak C—H...O hydrogen bonds and π–π stacking interactions link the molecules into a three-dimensional network.

The title molecule, C17H15N5, adopts a Z-shaped conformation, with the benzyl and benzodiazole substituents disposed on opposite sides of the plane of the triazole ring. A three-dimensional network is generated in the crystal by a combination of C—H...N hydrogen bonds and C—H...π(ring) interactions.

The title compound, C13H13NO3, lies on a mirror plane with an intramolecular C—H...O hydrogen bond enclosing an S(6) ring. In the crystal, weak C—H...O hydrogen bonds link the molecules into zigzag chains along the a-axis direction and π–π interactions, with a centroid-to-centroid distance of 3.7003 (2) Å, involving the pyridine and benzene rings of the oxoquinoline ring system, pack the molecules into parallel layers.

In the title compound, C19H13BrClN3, the chlorophenyl ring occupies an equatorial position with respect to the mean plane of the imidazopyridine unit, while the other phenyl ring is twisted by 4.1 (2)° with respect to the mean plane of the imidazopyridine unit. In the crystal, pairwise C—H...Br interactions link the molecules into dimers, forming an R22(16) ring motif. In addition, weak π–π stacking interactions stabilize the crystal packing.

In the title compound, C20H18N4O, the dihedral angle between the pyrazole and pyrazolone rings is 69.35 (3)° and an intramolecular C—H...O hydrogen bond encloses an R22(6) ring. In the crystal, the packing features N—H...O and C—H...O hydrogen bonds and C—H...π(ring) interactions.

The title compound,C23H26N4O7, adopts a Z-shaped conformation, with a dihedral angle between the mean planes of the dihydroindole and triazole rings of 70.36 (7)°. In the crystal, C—H...O interactions connect the molecules into zigzag chains running along the b-axis direction.

In the title molecule, C23H25FN4O7, the dihedral angle between the indole skeleton (r.m.s. deviation = 0.022 Å) and the triazole moiety is 74.67 (7)°. The molecules pack in a three-dimensional network in the crystal, being linked by C—H...O and N—H...O hydrogen bonds.

The asymmetric unit of the title compound, C11H8FNO2, consists of two independent molecules having different conformations and associated through pairwise C—H...F hydrogen bonds. These units form `stairstep' stacks along the b-axis direction via π–π stacking interactions between dihydroindole moieties, with interplanar spacings of 3.578 (3) and 3.627 (3) Å. The stacks are tied together by weak C—H...O hydrogen bonds.

The title imidazo [4,5-b] pyridine derivative, C16H14BrN3O2, crystallizes with two independent molecules (1 and 2) in the asymmetric unit. In molecule 1, the pendant phenyl ring is inclined to the imidazo[4,5-b]pyridine core by 43.10 (4)° while in molecule 2 the corresponding angle is 49.43 (4)°. The two molecules differ primarily in the conformations of the ester substituents. In the crystal, molecules are linked via C—H...N and C—H...O hydrogen bonds, forming sheets parallel to the ab plane.

In the title compound, C13H8BrN3S2, one propynyl substituent lies approximately in the plane of the pyridopyrazine ring system, while the other is twisted away from this plane. In the crystal, offset π–π stacking interactions between the pyridine and pyrazine rings with a centroid–centroid distance of 3.740 (1) Å stack the molecules along the a-axis direction. At the conclusion of the initial refinement, a significant residual peak remained in the difference map. This suggested an alternate location for the Br atom but at a very low occupancy. Further refinement with Br disordered over two sites yielded a population ratio for the two Br sites of 97:3. As the refined location of the minor Br site leads to unequal C—C—Br angles, we feel that the results indicate a `whole molecule' disorder rather than the presence of a minor amount of an isomer. Unfortunately, the very low amount of the second component of the disorder prevented the location of any of its other atoms.

In the title compound, C11H8ClNO2, the allyl side chain is almost perpendicular to the 5-chloroindoline-2,3-dione ring system, with a dihedral angle of 88.0 (3)°. In the crystal, C—H...O interactions link the molecules into layers lying parallel to the bc plane.

The title molecule, C9H6ClNO2, is almost planar, with an r.m.s. deviation of the fitted non-hydrogen atoms of 0.0922 (19) Å. In the crystal, molecules are connected through methyl-C—H...O(carbonyl) interactions into supramolecular helical chains along the b axis. Inter-chain π–π interactions lead to layers parallel to the ab plane [centroid–centroid distances = 3.4861 (13) to 3.9767 (12) Å]. The crystal studied was a non-merohedral twin with a ratio of the twin components of 0.8612 (12): 0.1388 (12).

In the title compound, C10H7NO3·H2O, O—H...O hydrogen bonds involving the carboxyl groups, the keto groups and the lattice water molecules form stepped sheets approximately parallel to {010} which are tied together by pairwise N—H...O interactions. The asymmetric unit contains two independent quinolone derivatives and two water molecules, one of which is disordered over two positions, of equal occupancy.

In the title compound, C14H15Br2NO2, the dihedral angle between the mean plane passing through the bromohexyl chain and the 5-bromoindoline ring system (r.m.s. deviation = 0.044Å) is 70.0 (3)°. In the crystal, molecules are connected by C—H...O hydrogen bonds, generating zigzag chains propagating along [010]. The packing is also influenced by inter-chain π–π interactions which form layers parallel to the ab plane [centroid–centroid distances = 3.765 (2) Å].

In the structure of the title compound, C20H27BrClNO2, the 5-chloroindoline-2,3-dione ring system is approximately planar, the largest deviation from the mean plane being 0.0237 (10) Å. The mean plane through the fused-ring system makes a dihedral angle of 61.00 (18)° with the mean plane passing through the 1-dodecyl chain. All C atoms of the dodecyl group adopt the planar zigzag arrangement normally observed in n-alkane compounds. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming chains parallel to the b axis.

The title compound, C15H10ClNO2, crystallizes with two molecules (A and B) in the asymmetric unit, which have almost identical conformations (r.m.s. overlay fit = 0.057 Å). In molecule A, the dihedral angle between the indole ring system (r.m.s. deviation = 0.025 Å) and the phenyl group is 71.39 (8)°. Equivalent data for molecule B are 0.023 Å and 71.43 (9)°. In the crystal, the A and B molecules are linked by a C—H...O hydrogen bond and aromatic π–π stacking is also observed [shortest centroid–centroid separation = 3.5810 (11) Å].

In the title compound, C16H14BrN3O2, the fused-ring system is essentially planar, with the largest deviation from the mean plane being 0.0216 (15) Å for the substituted N atom of the five-membered ring, the plane of which makes dihedral angles of 28.50 (7) and 77.48 (7)° with the terminal phenyl ring and the ethoxycarbonylmethyl group mean planes, respectively. In the crystal, C—H...N hydrogen bonds link the molecules into inversion dimers. These combine with weak C—H...N contacts to stack the molecules into columns along the b-axis direction.

The title molecule, C7H6BrN3, crystallizes with two molecules, A and B, in the asymmetric unit, with all non-hydrogen atoms lying on a crystallographic mirror plane. In the crystal, the molecules are linked into [100] chains of alternating A and B molecules by complementary N—H...N and C—H...N hydrogen bonds. The chains are associated through offset aromatic π–π stacking [shortest centroid–centroid separation = 3.6215 (9) Å] along the b axis.

In the title compound, C13H9BrClN3, the imidazopyridine fused-ring system is almost planar, with r.m.s. deviation of 0.006 (19) Å, and makes a dihedral angle of 29.32 (8)° with the mean plane of the 4-chlorophenyl group. In the crystal, C—H...N hydrogen bonds link the molecules into chains propagating in the [100] direction. Weak intermolecular π–π interactions between the five- and six-membered rings of the 3H-imidazo[4,5-b]pyridine moieties of neighbouring molecules [centroid–centroid distance = 3.8648 (12) Å] further consolidate the packing into layers parallel to the ab plane.