Preparation, spectroscopic, X-ray crystallographic, DFT, antimicrobial and ADMET studies of N-[(4-flourophenyl)sulfanyl]phthalimide.

N-[(4-Fluorophenyl)sulfanyl]phthalimide (C14H8FNO2S, FP) was synthesized and characterized using X-ray crystallography. It was then investigated via quantum chemical analysis using the density functional theory (DFT) approach, as well as spectrochemically using FT-IR and 1H and 13C NMR spectroscopy, and elemental analysis. The observed and stimulated spectra are in very good agreement for the DFT method. The in vitro antimicrobial activity of FP against three Gram-positive bacteria, three Gram-negative bacteria and two fungi were determined using the serial dilution method, and FP showed the highest antibacterial activity against E. coli, with a MIC of 128 µg ml-1. Druglikeness, ADME (absorption, distribution, metabolism and excretion) and toxicology studies were carried out to theoretically examine the drug properties of FP.

Inhibitory effects of sulfenimides on human and bovine carbonic anhydrase enzymes.

A series of sulfenimide derivatives (1a-i) were investigated as inhibitors of human (hCA-I, hCA-II) and bovine (bCA) carbonic anhydrase enzymes. The compounds were synthesised by the reaction of substituted thiophenols with phthalimide by means of an effective, simple and eco-friendly method and the structures were confirmed by IR, 1H NMR, 13C NMR, MS and elemental analysis. All derivatives except for the methyl derivative (1b) exhibited effective inhibitory action at low micromolar concentrations on human isoforms, but only four derivatives (1e, 1f, 1h, 1i) inhibited the bovine enzyme. The bromo derivative (1f) was found to be strongest inhibitor of all three enzymes with KI values of 0.023, 0.044 and 20.57 µM for hCA-I, hCA-II and bCA, respectively. Results of our study will make valuable contributions to carbonic anhydrase inhibition studies for further investigations since inhibitors of this enzyme are important molecules for medicinal chemistry.

Design, synthesis and spectroscopic and structural characterization of novel N-(2-hydroxy-5-methylphenyl)-2,3-dimethoxybenzamide: DFT, Hirshfeld surface analysis, antimicrobial activity, molecular docking and toxicology.

The novel compound N-(2-hydroxy-5-methylphenyl)-2,3-dimethoxybenzamide, C16H17NO4, I, was prepared by a two-step reaction and then characterized by elemental analysis and X-ray diffraction (XRD) methods. Moreover, its spectroscopic properties were investigated by FT-IR and 1H and 13C NMR. Compound I crystallized in the monoclinic space group P21/c and the molecular geometry is not planar, being divided into three planar regions. Supramolecular structures are formed by connecting units via hydrogen bonds. The ground-state molecular structure of I was optimized by the DFT-B3LYP/6-31G(d,p) method and the theoretical structure was compared with that obtained by X-ray diffraction. Intermolecular interactions in the crystal network were studied by two-dimensional (2D) and three-dimensional (3D) Hirshfeld analyses. The calculated electronic transition results were examined and the molecular electrostatic potentials (MEPs) were also determined. The in vitro antimicrobial activities of I against three Gram-positive bacteria, three Gram-negative bacteria and two fungi were determined. The compound was compared with several control drugs and showed better activity than the amoxicillin standard against Gram-positive bacteria B. subtilis, S. aureus and E. faecalis, and Gram-negative bacteria E. coli, K. pneumoniae and P. aeruginosa. The density functional theory (DFT)-optimized structure of the small molecule was used to perform molecular docking studies with proteins from experimentally studied bacterial and fungal organisms using AutoDock to determine the most preferred binding mode of the ligand within the protein cavity. A druglikeness assay and ADME (absorption, distribution, metabolism and excretion) and toxicology studies were carried out and predict a good drug-like character.

Synthesis, X-ray structure, antimicrobial activity, DFT and molecular docking studies of N-(thiophen-2-ylmethyl)thiophene-2-carboxamide.

In the present study, N-(thiophen-2-ylmethyl)thiophene-2-carboxamide, C10H9NOS2, (I), was obtained by the reaction of thiophene-2-carbonyl chloride and thiophen-2-ylmethanamine. Characterization of (I) was carried out using X-ray diffraction, spectroscopic techniques and elemental analyses. The DFT/B3LYP/6-311++G(d,p) theoretical level was successfully applied to calculate the optimized geometry and the local and global chemical activity parameters. The results obtained show good agreement between the experimental and theoretical geometrical parameters. The local and global chemical activity parameters were examined to determine the electrophilic and nucleophilic sites in (I). The natural bond orbital (NBO) analysis of (I) gives an efficient methodology for investigating the inter- and intramolecular bonding, as well as giving a convenient basis for investigating charge transfer or conjugative interactions in molecular systems. Also, the antimicrobial activity of (I) was investigated against eight microorganisms using the microdilution method and it is found to have an effective antibacterial activity. In addition, molecular docking studies were calculated in order to understand the nature of the binding of (I) with a lung cancer protein (PDB entry 1x2j).

Synthesis, Spectroscopic Characterization, Single-Crystal Structure, Hirshfeld Surface Analysis, and Antimicrobial Studies of 3-Acetoxy-2-methylbenzoic Anhydride.

We report a novel anhydride derivative, 3-acetoxy-2-methylbenzoic anhydride (AMA), obtained from the interaction of 3-acetoxy-2-methylbenzoyl chloride with 3-acetoxy-2-methylbenzoic acid. The synthesized compound was characterized by elemental analysis, IR, 1H NMR, and 13C NMR spectroscopic studies and single-crystal X-ray crystallography which revealed the crystallization of AMA as monoclinic with space group P21/c. A Hirshfeld surface analysis was performed to record various intermolecular interactions, indicating the stabilization of the AMA structure by the intermolecular weak C-H···O hydrogen bonds and π···π interactions. The title compound was screened for antibacterial and antifungal activities using a serial dilution technique under aseptic conditions. The results indicate that the title compound has significant antibacterial properties but showed no antifungal behavior.

Synthesis, Structural Investigation, Hirshfeld Surface Analysis, and Biological Evaluation of N-(3-Cyanothiophen-2-yl)-2-(thiophen-2-yl)acetamide.

In this study, a novel heterocyclic amide derivative, N-(3-cyanothiophen-2-yl)-2-(thiophen-2-yl)acetamide (I), was obtained by reacting 2-aminothiophene-3-carbonitrile with activated 2-(thiophen-2-yl)acetic acid in a N-acylation reaction and characterized by elemental analyses, FT-IR, 1H and 13C NMR spectroscopic studies, and single crystal X-ray crystallography. The crystal packing of I is stabilized by C-H···N and N-H···N hydrogen bonds. In addition, I was investigated computationally using the density functional theory (DFT) method with the B3LYP exchange and correlation functions in conjunction with the 6311++G(d,p) basis set in the gas phase. Fukui function (FF) analysis was also carried out. Electrophilicity-based charge transfer (ECT) method and charge transfer (ΔN) were computed to examine the interactions between I and DNA bases (such as guanine, thymine, adenine, and cytosine). The most important contributions to the Hirshfeld surface are H···H (21%), C···H (20%), S···H (19%), N···H (14%), and O···H (12%). An ABTS antioxidant assay was used to evaluate the in vitro antioxidant activity of I. The compound exhibited moderate antioxidant activity. The antimicrobial activity of the title molecule was investigated under aseptic conditions, using the microdilution method, against Gram-positive and Gram-negative bacterial strains, and it also demonstrated significant activity against yeasts (Candida glabrata ATCC 90030, Candida krusei ATCC 34135). The findings revealed that the molecule possesses significant antioxidant and antimicrobial properties.

Experimental and theoretical investigations on a furan-2-carboxamide-bearing thiazole: synthesis, molecular characterization by IR/NMR/XRD, electronic characterization by DFT, Hirshfeld surface analysis and biological activity.

A thiazole-based heterocyclic amide, namely, N-(thiazol-2-yl)furan-2-carboxamide, C8H6N2O2S, was synthesized and investigated for its antimicrobial activity. The structure was characterized by elemental analysis and IR, 1H NMR, and 13C NMR spectroscopy. The molecular and electronic structures were investigated experimentally by single-crystal X-ray diffraction (XRD) and theoretically by density functional theory (DFT) modelling. The compound crystallized in the monoclinic space group P21/n and the asymmetric unit contains two symmetrically independent molecules. Several noncovalent interactions were recorded by XRD and analysed with Hirshfeld surface analysis (HSA) calculations. Natural bond orbital, molecular electrostatic potential, second-order nonlinear optical and thermodynamic property analyses were also carried out using the DFT/B3LYP method. The title compound was evaluated for antimicrobial activity against eight microorganisms consisting of Gram-negative bacteria, Gram-positive bacteria and fungi. The compound showed good antimicrobial activity against the eight tested microorganisms. This suggests that the compound merits further study for potential pharmacological and medical applications.

Synthesis, crystal structure, spectroscopic features and Hirshfeld surfaces of 2-methyl-3-[(2-methyl-phen-yl)carbamo-yl]phenyl acetate.

The title compound, C17H17NO3, was synthesized, characterized by IR spectroscopy and its crystal structure was determined from single-crystal diffraction data. The asymmetric unit contains two mol-ecules, which adopt different conformations. In one mol-ecule, the acet-oxy and the terminal 2-methyl-phenyl groups are positioned on opposite sides of the plane formed by the central benzene ring, whereas in the other mol-ecule they lie on the same side of this plane. In the crystal, the mol-ecules are linked through strong N-H⋯O hydrogen bonds into chains along [010]. Hirshfeld surface analysis and fingerprint plots were used to investigate the inter-molecular inter-actions in the solid state.

Crystal structure of 2,3-dimeth-oxy-N-(4-nitro-phen-yl)benzamide.

In the title compound, C15H14N2O5, the benzene rings are nearly coplanar, making a dihedral angle of 4.89 (8)°. An intra-molecular N-H⋯O hydrogen bond occurs between the imino and meth-oxy groups. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into supra-molecular chains propagating along the a-axis direction. π-π stacking is observed between parallel benzene rings of neighbouring chains, the centroid-to-centroid distance being 3.6491 (10) Å. Three-dimensional Hirshfeld surface analyses and two-dimensional fingerprint plots have been used to analyse the inter-molecular inter-actions present in the crystal.

1,3-Bis(4-methylphenyl)triazene, 1-(4-chlorophenyl)-3-(4-fluorophenyl)triazene and 1-(4-fluorophenyl)-3-(4-methylphenyl)triazene.

The title 4,4'-disubstituted diphenyl-1,3-triazines, C14H15N3, (I), C12H9ClFN3, (II), and C13H12FN3, (III), each contain a triazene group (-N=N-NH-) having an extended conformation. The dihedral angles between the two benzene rings in (I), (II) and (III) are 4.3, 3.4 and 6.5 degrees , respectively. The molecules are almost entirely planar, with maximum deviations from the mean planes of 0.1087 (2), -0.1072 (7) and 0.1401 (3) A, respectively. In each compound, the molecules are linked by N-H...N hydrogen bonds to form chains and pack similarly in the crystal structures.