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Nanoparticles are key focus of research for a wide range of novel applications. As such, ZnFe2O4 magnetic nanoparticles were synthesized hydrothermally and characterized via scanning and transmission electron microscopies, powder X-ray diffraction, energy-dispersive X-ray and infrared spectroscopies, thermogravimetric analysis and magnetic measurements. They were used as a robust catalyst for the synthesis of a series of biologically active multi-substituted imidazoles using a multicomponent reaction by the reaction of benzil with various aromatic aldehydes, ammonium acetate and aliphatic amines ( N, N-dimethyl-1,3-propanediamine and 1-amino-2-propanol) under solvent-free conditions. The key advantages of this method are shorter reaction times, very high yield and ease of operation. The thermally and chemically stable, benign and economical catalyst was easily recovered using an external magnet and reused in at least five successive runs without an appreciable loss of activity. All of these novel synthesized compounds were characterized from spectral data and their purities were checked using thin-layer chromatography, giving one spot. Furthermore, the prepared compounds were tested for their anti-inflammatory activity. [ABSTRACT FROM AUTHOR]

Morpholinium hydrogen sulfate as an ionic liquid was employed as a catalyst for the synthesis of a biologically active series of multi-substituted imidazoles by a four-component reaction involving the combination of benzil with different aromatic aldehydes, ammonium acetate, and 1-amino-2-propanol under solvent-free conditions. The key advantages of this method are shorter reaction times, very high yield, and ease of processing. Furthermore, the resulting products can be purified by a non-chromatographic method and the ionic liquid catalyst is reusable. All of these novel compounds have been fully characterized from spectral data. The X-ray crystal structures of two representative molecules are also detailed. [ABSTRACT FROM AUTHOR]

This study aimed to isolate and identify three prenylflavonoids (cannflavin A, B, and C) from Cannabis sativa leaves using different chromatographic techniques. The potential of the isolated compounds against SARS-CoV-2 was suggested through several in silico analysis. Structural similarity studies against nine co-crystallized ligands of SARS-CoV-2's proteins indicated the similarities of the isolated cannflavins with the SARS-CoV-2 Papain-Like Protease (PLP) ligand, Y95 . Then, flexible allignment study confirmed this similarity. Docking experiments showed successful binding of all cannflavins within the active pocket of PLP, with energies comparable to Y95 . Among them, cannflavin A demonstrated the most similar binding mode, while cannflavin C exhibited the best energy. Molecular dynamics (MD) simulations and MM-GPSA confirmed the accurate binding of cannflavin A to the PLP. In silico ADMET studies indicated favourable drug-like properties for all three compounds, suggesting their potential as anti-SARS-CoV-2 agents. Further In vitro and In vivo investigations are necessary to validate these findings and establish their efficacy and safety profiles.

The title compound, C 24 H 21 N 3 O 3 , crystallizes with two unique but closely r.m.s. overlay fit = 0.215 Å) comparable mol-ecules (1 and 2) in the asymmetric unit of the triclinic unit cell. In molecule 1, the dihedral angles between the central imidazlole ring and the benzene-ring substituents are 42.51 (9), 45.41 (9) and 56.92 (8)°, respectively. Comparable data for molecule 2 are 39.36 (10), 34.45 (11) and 60.34 (8)°, respectively. The rings at the 2-positions carry p -nitro substituents that subtend dihedral angles of 12.9 (4)° in mol-ecule 1 and 11.7 (4)° in mol-ecule 2 to their respective benzene ring planes. The imidazole rings also have propan-2-ol substituents on the 1-N atoms, which adopt extended conformations for the N-C-C-C chains. In the crystal, classical O-H⋯N hydrogen bonds combine with C-H⋯O, C-H⋯N and C-H⋯π(ring) hydrogen bonds and stack the molecules along the a -axis direction.

The title compound, C 24 H 21 ClN 2 O, crystallizes with two unique mol-ecules in the asymmetric unit. In each mol-ecule, the central imidazole ring is substituted at the 2-, 4- and 5-positions by benzene rings. The 2-substituted ring carries a Cl atom at the 4-position. One of the imidazole N atoms in each mol-ecule has a propan-2-ol substituent. In the crystal, a series of O-H⋯N, C-H⋯O and C-H⋯Cl hydrogen bonds, augmented by several C-H⋯π(ring) inter-actions, generate a three-dimensional network of mol-ecules stacked along the a -axis direction.

The central imidazole ring of the title compound, C24H20Cl2N2O, is twisted with respect to with the planes of the 2,6-di-chloro-benzene and two phenyl rings, making dihedral angles of 74.06 (18), 28.52 (17) and 67.65 (18)°, respectively. The phenyl ring not adjacent to the N-bonded 2-hy-droxy-propyl group shows the greatest twist, presumably to minimize steric inter-actions. In the crystal, mol-ecules are linked by O-H⋯N and C-H⋯O hydrogen-bond contacts into chains along the a-axis direction. The series of parallel chains form a two-dimensional sheet approximately parallel to the bc diagonal. In addition, C-H⋯π inter-actions are observed between the sheets. The atoms of the 2-hy-droxy-propyl group and the N atom of the 1H-imidazole ring to which it is bonded are disordered over two sets of sites, with an occupancy ratio of 0.722 (5):0.278 (5). The structure was refined as an inversion twin.

The central imidazole ring in the title compound, C28H30N2O2, makes dihedral angles of 28.42 (13), 71.22 (15) and 29.50 (14)°, respectively, with the phenyl rings in the 4- and 5-positions and the 3,4-di-meth-oxy-phenyl group. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯N hydrogen bonds, weak π-π stacking inter-actions [centroid-centroid distance = 3.760 (2) Å] and C-H⋯π contacts, forming a three-dimensional network.

The title compound, C26H25BrN2, is isomorphous with the chloro derivative [2-(4-chloro-phen-yl)-1-pentyl-4,5-diphenyl-1H-imidazole; Mohamed et al. (2013 ▶). Acta Cryst. E69, o846-o847]. The two phenyl rings and the 4-bromo-phenyl ring are oriented at dihedral angles of 30.1 (2), 64.3 (3) and 42.0 (2)°, respectively, with respect to the imidazole ring. In the crystal, mol-ecules stack in columns along the b-axis direction, however, there are no significant inter-molecular inter-actions present.

In the title compound, C26H25ClN2, the phenyl rings and the 2-(4-chloro-phen-yl) group make dihedral angles of 30.03 (11), 67.49 (12) and 41.56 (11)°, respectively, with the imidazole ring. In the crystal, the mol-ecules inter-act with each other via very weak C-H⋯π contacts, forming layers parallel to (110).

In the title compound, C26H24N2O2, the two phenyl and the 2,5-di-meth-oxy-phen-yl rings are inclined to the imidazole ring at dihedral angles of 30.38 (8), 56.59 (9) and 73.11 (9)°, respectively. In the crystal, mol-ecules are linked by pairs of C-H⋯O inter-actions into centrosymmetric dimers with graph-set notation R 2 (2)(8). C-H⋯π inter-actions are also observed.

In the title compound, C20H18ClN5S, the toluene and triazole rings are oriented almost perpendicular to each other, making a dihedral angle of 89.97 (9)°, whereas the dihedral angle between cholorophenyl and pyrazole rings is 54.57 (11)°. In the crystal, pairs of N-H⋯N hydrogen bonds link the mol-ecules into inversion dimers. Weaker C-H⋯S and C-H⋯Cl inter-actions are also present.

The title compound, C24H19ClN2, crystallizes with two independent mol-ecules in the asymmetric unit. The prop-2-enyl substituents on the imidazole rings adopt similar conformations in the two mol-ecules. The 4-and 5-substituted phenyl rings and the benzene ring make dihedral angles of 67.06 (8), 5.61 (8) and 41.09 (8)°, respectively, with the imadazole ring in one mol-ecule and 71.53 (8), 28.85 (8) and 41.87 (8)°, respectively, in the other. The crystal structure features C-H⋯π inter-actions and weak π-π stacking inter-actions [centroid-centroid distances = 3.6937 (10) and 4.0232 (10) Å] between the chloro-phenyl rings, which form a three-dimensional supramolecular structure.

The title compound, C26H24Cl2N2, crystallizes with two independent mol-ecules (1 and 2) in the asymmetric unit. In mol-ecule 1, the two phenyl and 2,6-di-chloro-phenyl rings are inclined to the imidazole ring at angles of 74.12 (14), 26.13 (14) and 67.30 (14)°, respectively. In mol-ecule 2, due to the different mol-ecular environment in the crystal, the corresponding angles are different, viz. 71.72 (15), 16.14 (15) and 80.41 (15)°, respectively. In the crystal, mol-ecules 1 and 2 are linked by C-H⋯Cl inter-actions, and inversion-related 2 mol-ecules are linked by C-H⋯π inter-actions. There are no other significant inter-molecular inter-actions present.

In the title compound, C19H16BrClO4, both the fused xanthene rings and one of the cyclo-hexane rings adopt envelope conformations, while the other cyclo-hexane ring is in a chair conformation. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming infinite chains running along [10-1] incorporating R 2 (2)(16) ring motifs. In addition, C-H⋯π inter-actions and weak π-π stacking inter-actions [centroid-centroid distance = 3.768 (3) Å] help to consolidate the packing.

In the title compound, C24H22N2O2, the central imidazole ring makes dihedral angles of 49.45 (8), 88.94 (9) and 19.43 (8)° with the benzene ring and the two phenyl rings, respectively. The dihedral angle between the phenyl rings is 77.86 (9)°, and they form dihedral angles of 49.06 (9) and 67.31 (8)° with the benzene ring. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds, forming chains along the b axis. These chains are connected by C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (100). In addition, C-H⋯π inter-actions are also observed. The terminal C and O atoms of the ethanol group are disordered over two sets of sites with an occupancy ratio of 0.801 (5):0.199 (5).

In the title compound, C(16)H(14)ClN(3)O(2)S, the dihedral angle between the benzene and pyrazole rings is 52.75 (2)°, while that between the pyrazole and 4-chloro-phenyl rings is 54.0 (3)°. The terminal sulfonamide group adopts an approximately tetra-hedral geometry about the S atom with a C-S-N angle of 108.33 (10)°. In the crystal, pairs of N-H⋯N hydrogen bonds lead to the formation of inversion dimers. These dimers are linked via a second pair of N-H⋯N hydrogen bonds and C-H⋯O interactions, forming a two-dimensional network lying parallel to the bc plane. The two-dimensional networks are linked via C-H⋯Cl interactions, forming a three-dimensional structure.

The title compound, C27H28N2O, is a lophine (2,4,5-triphenyl-1H-imidazole) derivative with an n-pentyl chain on the amine N atom and a 4-meth-oxy substituent on the benzene ring. The two phenyl and meth-oxy-benzene rings are inclined to the imidazole ring at angles of 25.32 (7), 76.79 (5) and 35.42 (7)°, respectively, while the meth-oxy substituent lies close to the plane of its benzene ring, with a maximum deviation of 0.126 (3) Å for the meth-oxy C atom. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R2(2)(22) loops. These dimers are stacked along the a-axis direction.

The mol-ecular conformation of the title compound, C13H8BrFN2O3, is essentially planar, with maximum deviations of 0.076 (1) and -0.080 (2) Å for the O atoms of the NO2 group. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond, forming an S(6) ring motif. In the crystal, pairs of mol-ecules are linked via two pairs of C-H⋯O hydrogen bonds, forming inversion dimers that enclose R(2)2(7)R(2)2(10)R(2)2(7) ring motifs.

In the title compound, C19H17NO2, the dihedral angle between the benzene ring and the naphthalene ring system is 9.72 (5)°, while the torsion angle of the C-N-C-C bridging group is 179.24 (17)°. The methyl group of the 1-phenyl-ethanol moiety is disordered over two positions with a refined occupancy ratio of 0.775 (5):0.225 (5). The mol-ecular conformation is stabil-ized by an intra-molecular N-H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming zigzag chains propagating along the c-axis direction. Neighbouring chains are linked via C-H⋯O inter-actions, forming a two-dimensional slab-like network parallel to the bc plane.

The asymmetric unit of the title compound, C34H16O5, contains two independent mol-ecules (A and B) with similar conformations. The two benzene rings attached to the nine-membered ring are inclined to one another at 63.62 (14)° in mol-ecule A and 68.23 (12)° in mol-ecule B. One intra-moleculer C-H⋯O hydrogen bond occurs in mol-ecule A and two are observed in mol-ecule B. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming a three-dimensional network structure with R(2)2(10) and R(2)2(24) ring motifs. Aromatic π-π stacking interactions [centroid-centroid distances = 3.7572 (19), 3.6996 (19) and 3.7043 (19) Å] are also observed. The unit cell contains a pair of voids of 37 (2) Å(3) about an inversion centre but the residual electron density (highest peak = 0.19 e Å(-3) and deepest hole = -0.20 e Å(-3)) in the difference Fourier map suggests that no solvent mol-ecule occupies this void.

The asymmetric unit of the title compound, C(25)H(22)N(2)O, contains two independent mol-ecules (A and B), with significantly different conformations. In mol-ecule A, the central imidazole ring makes dihedral angles of 88.26 (10) and 12.74 (11)° with the two phenyl rings, and 22.06 (9)° with the benzene ring. In mol-ecule B, one of the phenyl rings is disordered over two sites, each having an occupancy of 0.5. Here the central imidazole ring forms dihedral angles of 79.24 (10)° with the ordered phenyl ring, and 3.5 (5) and 22.6 (5)° with the two parts of the disordered phenyl ring. The dihedral angle involving the benzene ring is 67.49 (10)°. The -N-C(H(2))-C(H)-C(H(2)) torsion angles of the prop-1-ene group in the two mol-ecules are very similar, 0.5 (3) and 1.3 (4)° for mol-ecules A and B, respectively. The crystal structure is stabilized by C-H⋯π inter-actions.

In the title compound, C(26)H(24)N(2)O(2), the planar 1H-imidazole ring makes dihedral angles of 35.78 (4), 26.35 (5) and 69.75 (5)°, respectively, with the dimeth-oxy-phenyl ring and the phenyl rings in the 4- and 5-positions. In the crystal, C-H⋯O hydrogen bonds connect neighbouring mol-ecules, forming infinite chains running along the b axis. Furthermore, the crystal structure exhibits a C-H-⋯π inter-action between a methyl H atom and a phenyl ring from an adjacent mol-ecule.