Synthesis,Computational, Electronic spectra,and molecular docking studies of 4-((diphenylmethylene)amino)-N-(pyrimidin-2-yl)benzenesulfonamide

The 4-((diphenylmethylene)amino)-N-(pyrimidin-2-yl)benzenesulfonamide (BENDA) was synthesized and characterized by the Infrared, UV-Visible, and NMR analysis. Using density functional theory, the current work is a set of theoretical studies on BENDA. The compound molecular structure and geometry were defined using DFT. Topological studies, like ELF, LOL, ALIE, and RDG studies, were done with the Multiwfn-3.8 to find the main binding areas and weak interactions in the molecule. Using the IEFPCM solvation model was used to study the calculated UV-Visible spectrum. The HOMO-LUMO, MEP, and NLO properties were carried out in the gas phase. The NBO calculations are used to study how charges move between and within the molecule and the stability of this molecule. A pharmacological analysis is done using an online tool like Swiss-ADME, to see if the molecule could be a potential drug candidate; this evaluation looks at the drug-likeness, ADME, and eco-friendly toxicity properties of the BENDA molecule. Auto-dock suite and Discovery studio Visualizer are used to do molecular docking against 5UVC protein.     

Synthesis,structural, computational,electronic spectra,wave function properties and molecular docking studies of (Z)-4-(((5-methylfuran-2-yl)methylene)amino)-N-(thiazol-2-yl)benzenesulfonamide

The (Z)-4-(((5-methylfuran-2-yl) methylene)amino)-N -(thiazol-2-yl) benzene sulfonamide (5M2FTH) was synthesized and characterized by the Infrared, UV–Visible, and NMR analysis. Using density functional theory, the current work is a set of theoretical studies on 5M2FTH. The compound molecular structure and geometry were defined using DFT. Topological studies, like ELF, LOL, ALIE, and RDG studies, were done with the Multiwfn-3.8 to find the main binding areas and weak interactions in the molecule. UV spectra was simulated using TD-DFT with implicit solvation model. The HOMO-LUMO, MEP, and NLO properties were carried out in the gas phase. The NBO calculations are used to study how charges move between and within the molecule and stability of this molecule. Pharmacological analysis was performed using Swiss-ADME and found that the compound is a potential drug candidate. PASS analysis revealed that the molecule can show antiparasitic properties which is confirmed by molecular docking against the target protein.     

Synthesis,structural, spectral,computational, docking and biological activities of Schiff base (E)-4-bromo-2-hydroxybenzylidene) amino)-N-(pyrimidin-2-yl) benzenesulfonamide from 5-bromosalicylaldehyde and sulfadiazine

The newly synthesized, characterized, and theoretically investigated Schiff base compound (E)-4-bromo-2-hydroxybenzylidene) amino)-N-(pyrimidin-2-yl) benzenesulfonamide (5BRSDA). Sulfadiazine and 5-bromosalicylaldehyde Schiff-base were the building blocks for the new compound. We were surprised by the variety in the structure of the results. By employing density functional theory (DFT), researchers were able to analyze the new compound molecular properties, geometric optimization, vibrational, frontier molecular orbitals, and energy evaluation. In addition, disc well diffusion was used to test the compounds antibacterial and antifungal properties. As compared to free ligands, the compound had a more potent pathogenic effect on the tested microbes, according to the findings. An in-depth molecular docking study on 1NTA provided new information about the inhibitory effects it has on pathogenic microbes. When compared to a literature survey, comparative analysis revealed that the titled compound had higher antibacterial and antifungal activity.     

Synthesis,computational, molecular docking studies and photophysical properties of (Z)-N-(pyrimidin-2-yl)-4-(thiophen-2-ylmethylene)amino) benzenesulfonamide

The (Z)-N-(pyrimidin-2-yl)-4-(thiophen-2-ylmethylene)amino) benzenesulfonamide (TH2DA) were synthesized and characterized by the Infrared, UV–Visible, and NMR analysis. Using density functional theory, the current work is a set of theoretical studies on TH2DA. The compound molecular structure and geometry were defined using DFT. Topological studies, like ELF, LOL, ALIE, and RDG studies, were done with the Multiwfn-3.8 to find the main binding areas and weak interactions in the molecule. Using the IEFPCM solvation model were used to study the calculated UV–Visible spectrum. The HOMO-LUMO, MEP, and NLO properties were carried out in the gas phase. The NBO calculations are used to study how charges move between and within the molecule and stability of this molecule. A pharmacological analysis is done using online tool like Swiss-ADME, to see if the molecule could be potential drug candidate; this evaluation looks at the drug-likeness, ADME and eco-friendly toxicity properties of the TH2DA molecule. Auto-dock suite and Discovery studio Visualizer are used to do molecular docking studies.     

(E)-4-((4-chlorobenzylidene)amino)-N-(thiazole-2yl) benzenesulfonamide: Synthesis,characterization and electronic structure theory and docking studies

Spectroscopic methods (NMR, UV–vis) were utilized to get an understanding of the molecular structure of the (E)-4-((4-chlorobenzylidene)amino)-N-(thiazole-2yl) benzenesulfonamide (4CLBTH). The DFT/B3LYP/cc-pVDZ, were used in the theoretical study of the compound. Calculations using DFT can produce geometrical parameters such as bond lengths and bond angles. The GIAO method was utilized in DMSO to calculate the ¹H and ¹³C NMR for TMS. These results were then compared to the observed data. The UV–Vis spectrum of 4CLBTH was computed by using the B3LYP with the cc-pVDZ basis set. Using theoretical calculations, an investigation into the FMO analysis and the MEP were carried out. The theoretical findings and the experimental findings are in reasonable agreement with one another. The molecular docking was investigated by the autodock suite and visualised using the discovery studio visualizer. The multiwfn software was used to calculate the wavefunction studies.     

Synthesis,characterization, computational,excited state properties,wave function,and molecular docking studies of (E)-4-((2-hydroxybenzylidene)amino)N-(thiazol-2-yl) benzenesulfonamide

The compound (E)-4-((2-hydroxybenzylidene)amino)N-(thiazol-2-yl) benzene sulfonamide (SATH) was synthesized and characterized by the Infrared, UV–Visible, and NMR analysis. Using density functional theory, the current work is a set of theoretical studies on SATH. The compound molecular structure and geometry were defined using DFT. Topological studies, like ELF, LOL, ALIE, and RDG studies, were done with the Multiwfn-3.8 to find the main binding areas and weak interactions in the molecule. Using the IEFPCM solvation model was used to study the calculated UV–Visible spectrum. The HOMO-LUMO, MEP, and NLO properties were carried out DFT/B3LYP/cc-pVDZ basis set in the gas phase. The NBO calculations are used to study how charges move between and within the molecule and the stability of this molecule. A pharmacological analysis is done using an online tool like Swiss-ADME, to see if the molecule could be a potential drug candidate; this evaluation looks at the drug-likeness, ADME, and eco-friendly toxicity properties of the PFPT molecule. Auto-dock suite and Discovery studio Visualizer are used to do molecular docking against 6ZZB protein.     

Synthesis,spectral analysis,antibacterial activity,quantum chemical studies and supporting molecular docking of Schiff base (E)-4-((4-bromobenzylidene) amino)benzenesulfonamide

A new Schiff base (E)-4-((4-bromobenzylidene) amino) benzenesulfonamide (M2) was synthesized by the reaction between 4-bromobenzaldehyde and sulfanilamide followed by characterization using IR, Raman, UV–Visible, ¹HNMR, and ¹³CNMR spectral techniques. This was followed by electronic structure studies using DFT and TD-DFT. We simulated the IR spectrum using B3LYP/6-31+G(d,p) level of theory, followed by a comparison with experimental spectra and detailed potential energy distribution and vibrational assignment analysis. The comparison of experimental UV and simulated UV spectrum using TD-DFT B3LYP/6-31+G(d,p) in DMSO solvent atmosphere gave good agreement. As Schiff bases are biologically active, we checked for the potential activity of the synthesized compound with the help of ADMET prediction and found it to be active. Wavefunctions related properties like ELF, LOL, and ELF are also reported. Prediction of biological activity spectrum study indicated possible antibacterial activity against bacteria, which is supported by molecular docking against Staphylococcus aureus (3U2D) protein with a docking score of ?7.1 kcal/mol. Experimental antibacterial study using the compound and standard drugs confirmed this prediction.     

Synthesis,computational, experimental antimicrobial activities and theoretical molecular docking studies of (E)-4-((4-hydroxy-3-methoxy-5-nitrobenzylidene) amino)-N-(thiazole-2-yl) benzenesulfonamide

The compound (E)-4-((4-hydroxy-3-methoxy-5-nitrobenzylidene) amino)-N-(thiazole-2-yl) benzene sulfonamide (5NVTH) was synthesized and characterized by the Infrared, UV-Visible, and NMR analysis. The compound theoretical study was done by using DFT. The compound molecular structure and geometry were defined using DFT. Topological studies, like ELF, LOL, ALIE, and RDG studies, were done with the Multiwfn-3.8 to find the main binding areas and weak interactions in the molecule. Using the IEFPCM solvation model was used to study the calculated UV-Visible spectrum. The HOMO-LUMO, MEP, and NBO properties were carried out in the gas phase. The NBO calculations are used to study how charges move between and within the molecule and the stability of this molecule. A pharmacological analysis is done using an online tool like Swiss-ADME, to see if the molecule could be a potential drug candidate; this evaluation looks at the drug-likeness, ADME, and eco-friendly toxicity properties of the 5NVTH molecule. Auto-dock suite is used for molecular docking study and discovery studio is used for analyzing the docking results. Antimicrobial activity studies indicate the compound Klebsiella pneumonia and Candida albicans have good antibacterial and antifungal activity compared to positive control and other microorganisms.     

Synthesis,spectral characterization,molecular docking studies,biological activity of (E)-2-((E)-3-(3,4,5-trimethoxyphenyl)allylidene) and (E)-N-phenyl 2-((E)-3-(3,4,5-trimethoxyphenyl)allylidene)hydrazinecarbothioamides and their Cu(II) complexes

Two slightly distorted octahedral complexes of copper(II) with (E)-2-((E)-3-(3,4,5-trimethoxyphenyl)allylidene)hydrazinecarbothioamide (L1) common name 3,4,5-trimethoxy-cinnamaldehydethiosemicarbazone and (E)-N-phenyl-2-((E)-3-(3,4,5-trimethoxyphenyl)-allylidene)hydrazinecarbothioamide (L2) common name 3,4,5-trimethoxycinnamaldehyde-4-phenylthiosemicarbazone have been synthesized. The two free ligands and their copper(II) complexes were characterized by spectroscopic techniques like FT-IR, FT-Raman, UV, EPR, Powder X-ray diffraction and cyclic voltammetry. The EPR spectra evidenced a rhombically distorted octahedron geometry for both the copper(II) complexes. The band gap calculations for the ligands L1, L2 and their complexes Cu(L1)₂Cl₂ and Cu(L2)₂Cl₂ were found to be 2.98, 2.61, 2.66 and 2.50 eV respectively. Cu(L1)₂Cl₂ and Cu(L2)₂Cl₂ have shown 50% of viability at 80 μg/ml and 60 μg/ml. The anti-oxidant activity study revealed that the compounds are good reductants of DPPH radical. Moderate to good anti-bacterial activity is shown by the compounds against the Gram-positive and Gram-negative bacteria. Molecular docking studies have been carried out to predict the orientation and binding mode of analysis in the active site. The synthesized ligand and complex well occupy (catalytic triad and adenine-binding site) in the active site of β-ketoacyl-acyl carrier protein synthase III enzyme, and also well occupy in helix 11 (in the DCS complex) of human estrogen receptor. Moreover they form water mediated hydrogen bond and hydrogen bond with Cys530 residue.     

Synthesis,enzymes inhibitory properties and characterization of 2- (bis (4-aminophenyl) methyl) butan-1-ol compound: Quantum simulations,and in-silico molecular docking studies

In this study to be presented, the BAPMB molecule was synthesized and structurally characterized. All calculations were applied using the detailed DFT/B3LYP method with 6-311G (d, p) and SDD depended on the stable phase geometry of the molecule. Also, various HOMO-LUMO energy gaps, inter-orbital intramolecular interactions of the natural bond, and electro-static surface mapping actions were also realized. The molecule was characterized by NMR spectroscopic analysis. Besides, LC/MS data were acquired. In this analysis, fragment ions (m/z 168.9) of BAPMB were obtained as 137.8, 179.9, 198, 201.5, and 228.0 approximately. Also, molecular docking was performed while examining the exact binding site and binding mechanism of the ligand on the protein. In the study, glide scores in binding affinity with BAPMB – AChE, BAPMB – BChE, and BAPMB – GST, respectively; It was found to be −7.228 ​cal/mol, −7.205 ​cal/mol, −6.07 ​cal/mol and BAPMB - AChE was found to be more effective with receptor binding score. BAPMB was analyzed for its inhibition features counter AChE, BChE, and GST enzymes that exhibit effective inhibition. AChE, BChE, GST enzymes were powerfully inhibited by BAPMB. BChE showed excellent activity, particularly in comparison to standard tacrine. Eventually, AIM analysis was performed to search intermolecular interactions in the BAPMB compound.     

Investigations on crystal structure of a novel 3-((4,6-dimethylpyrimidin-2-yl)amino)isobenzofuran-1(3H)-one,and related theoretical studies

In this report, 3-((4,6-dimethylpyrimidin-2-yl)amino)isobenzofuran-1(3H)-one have been synthesized via reaction between phthalaldehydic acid and 2-amino-4,6-dimethylpyrimidine in 90% yields and characterized by Infrared (IR), Nuclear Magnetic Resonance (NMR), Ultraviolet–visible (UV–Vis), X-ray single crystal diffraction techniques. The single-crystal X-ray analysis shows that the title compound crystallizes in the triclinic space group P-1 with unit-cell parameters a = 7.9351(4) Å, b = 11.1687(6) Å, c = 16.1281(9) Å, α = 73.713(5)°, β = 80.362(5)°, γ = 72.882(4)° and Z = 4. A theoretical study with hybrid functional B3LYP 6-311G (d, p) basis set have been used in calculations. The structural and electronic properties have been detailed. The title compound was screened for its antioxidant activity by (1,1-diphenyl-2-picryl hydrazyl) free radical scavenging (DPPH), Ferric ion reducing antioxidant power (FRAP), total phenolic contents (TP) assays and its ferrous ions chelating property. Electronic absorption titration, thermal denaturation measurement and viscosity techniques were used to determine the interaction between double stranded DNA (dsDNA) and compound 1. In three techniques, the mode of binding of compound 1 to dsDNA is minor groove. The UV–Vis measurement results allowed the calculation of the binding constant showing the binding strength of compound 1 to dsDNA was calculated as 8.13 × 10⁴ ± 0.07 L mol⁻¹. Moreover, the molecular docking calculations have been performed to investigate the compound–DNA interactions, computationally. In molecular docking calculations, it was observed that for the title compound, the lowest energy docking pose takes place in the minor groove of DNA and in addition to minor groove binding, interactions between the compound and the consecutive base pairs of DNA which may cause a partial intercalation were also observed. Results showed that title compound – DNA complex is stabilized by several hydrogen bonds, and Pi-alkyl interactions also take part in the stabilization of the complex. Binding affinities of the lowest energy docking pose of the title compound was found to be −8.3 kcal/mol.     

Synthesis,spectral and quantum mechanical studies and molecular docking studies of Schiff base (E)2-hydroxy-5-(((4-(N-pyrimidin-2-yl)sulfamoyl)phenyl)imino)methyl benzoic acid from 5-formyl salicylic acid and sulfadiazine

A new Schiff base (E)2-hydroxy-5-(((4-(N-pyrimidin-2-yl)sulfamoyl)phenyl)imino)methyl benzoic acid (5FSADA) compound was synthesized by condensation of 5-formyl salicylic acid and sulfadiazine, and the product formed was characterized using FTIR and UV–Visible spectroscopy. The geometry was optimized using DFT. The FTIR were computed from DFT and is compared with experimental spectra, followed by detailed vibrational assignment, which shows that the experimental and simulated data is in close agreement. The UV–Vis spectrum calculated using TD-DFT, IEFPCM solvation model with DMSO as solvent. Wave function based properties like localized orbital locator, electron localization function and non-covalent interactions has been studied extensively. The physical properties (ADMET) of the compound 5FSADA indicated that the compound has excellent drug likeness and PASS studies showed that it has anti-infective properties, which is confirmed by a docking score of −9.0 ​kcal/mol.     

Spectroscopic,anti-bacterial,anti-cancer and molecular docking of Pd(II) and Pt(II) complexes with (E)-4-((dimethylamino)methyl)-2-((4,5-dimethylthiazol-2-yl)diazenyl)phenol ligand

New ligand (E)-4-((dimethylamino)methyl)-2-((4,5-dimethylthiazol-2-yl)diazenyl)phenol (HDmazo) was prepared by the coupling reaction between 4,5-dimethylthiazol-2-amine and 4-((dimethylamino)methyl)phenol. Moreover, the [MCl₂(HDmazo)] and [M(HDmazo)₂] [M^II = Pd and Pt] were prepared using the direct reaction of equivalent molar of HDmazo and Na₂PdCl₄ or K₂PtCl₄. The HDmazo and its complexes were investigated by different spectroscopic techniques. In complexes (1–2) HDmazo ligand behaves as bidentate style through the nitrogen of azo group and nitrogen of thiazole ring towards Pd(II) and Pt(II). Or in a bidentate fashion via the oxygen atom of the hydroxylate group and nitrogen atom of azo group as mono-anion in complexes (3–4). Further, the study of biological activity against four pathogenic bacteria showed that compound (3) exhibited good activity compared to other compounds. Additional the anti-tumor action against A2870 cell lines was screened, and the complexes (1) and (2) displayed good activity with 7.45 ± 0.98 µM and 13.23 ± 1.43 µM, respectively. The binding mechanism of the prepared compounds with EGFR tyrosine kinase, was investigated using molecular docking experiments.     

Synthesis,characterization, computational,excited state properties,wave function and molecular docking studies of (E)-1-(perfluorophenyl)-N-(p-tolyl) methanimine

The compound (E)-1-(perfluorophenyl)-N-(p-tolyl)methanimine (PFPT) was synthesized and characterized by the Infrared, UV–Visible, and NMR analysis. Using density functional theory, the current work is a set of theoretical studies on PFPT. The compound molecular structure and geometry were defined using DFT. Topological studies, like electron localized function, localized orbital locator, average localized ionization energy, and reduced density gradient studies, were done with the Multiwfn-3.8 to find the main binding areas and weak interactions in the molecule. Using the IEFPCM solvation model used to study the calculated UV–Visible spectrum, we used two different solvents. The HOMO-LUMO, MEP, and NLO properties were carried out by DFT/B3LYP/cc-pVDZ in the gas phase. The NBO calculations are used to study how charges move between and within the molecule and the stability of this molecule. A pharmacological analysis is done using an online tool like Swiss-ADME, to see if the molecule could be a potential drug candidate; this evaluation looks at the drug-likeness, ADME, and eco-friendly toxicity properties of the PFPT molecule. Auto-dock suite and Discovery studio Visualizer are used to do molecular docking against 2QFA protein.     

An efficient one-pot three-component synthesis of 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-arylacrylonitriles and their cytotoxic activity evaluation with molecular docking

A facile, convenient and one-pot three-component method has been outlined for the synthesis of title compounds by treating equimolar amounts of 3-(2-bromoacetyl)-2H-chromen-2-one (2) with 2-cyanothioacetamide (3) and various aryl/heteryl aldehydes (5 or 7) independently. The effect of solvent and catalyst on this one-pot reaction has been studied and the use of l-proline in ethanol was found to be effective to achieve the target compounds (6 & 8) in fair yields. These synthesized compounds were further assessed for the anti-hepatoma activity, and their action mechanism was also investigated by using molecular docking studies. All the compounds 6(a-h) & 8(a-f) manifested excellent potency for anti-hepatoma activity. It should be noted that, compounds 6e, 6f have exhibited almost equipotent activity with reference to standard drug Nexavar.     

Structure elucidation,DNA binding,DFT, molecular docking and cytotoxic activity studies on novel single crystal (E)-1-(2-fluorobenzylidene)thiosemicarbazide

Compound 3 {(E)-1-(2-fluorobenzylidene)thiosemicarbazide} – a new Schiff base of thiosemicarbazide has been synthesized, characterized and reported for crystal structure. Planer side chain in the crystal structure was observed co-planer with aromatic ring plane and molecules were connected into centrosymmetric dimmers via intermolecular hydrogen bonding. DFT geometry optimization and the relevant quantum parameters indicated unstable and reactive nature of compound 3. Experimental and theoretical findings for DNA binding by UV–visible, cyclic voltammetry and molecular docking studies showed consistency in kinetic (K_b) and thermodynamic (ΔG) parameters and that compound 3 significantly interacted with DNA via intercalation. Viscometric analysis further comprehended intercalation as possible binding mode of the compound with DNA and non-denaturing of DNA in the presence of 10% aqueous DMSO. Docked parameters further assured the drug like characteristics of the investigated compound as fit in Lipinski’s criteria. Dose dependant cytotoxic activity of compound 3 against human Huh-7 cell line indicated its anti-cancer potential at 100?µg/ml concentration.     

Copper(II) complex with 6-(3,5-dimethyl-1H-pyrazol-1-yl)-2-(pyridin-2-yl)pyrimidin-4-amine: synthesis,crystal structure,and electronic spectroscopy

A copper(II) complex with 6-(3,5-dimethyl-1H-pyrazol-1-yl)-2-(pyridin-2-yl)pyrimidin-4-amine (L), [CuLCl₂], has been synthesized. This compound is formed irrespective of the Cu?:?L molar ratio (Cu?:?L?=?1?:?1, 2?:?1, and 20?:?1) in the MeOH/H₂O/DMF mixture as a single product. ESI-MS data demonstrate that the additional amount of CuCl₂ above the Cu?:?L?=?1?:?1 molar ratio, is effectively solvated, and high-nuclearity species are formed in trace amounts in the solution. The complex adopts a distorted square-pyramidal geometry with two chlorides and three nitrogen atoms from L. The electronic spectrum of the complex contains a broad band with a maximum at 12,820?cm^?1 within the region characteristic for square-pyramidal chromophores CuA₅ (A?=?Cl, N). Due to Cu?···?Cl contacts, the molecules of [CuLCl₂] form the dinuclear [CuLCl₂]₂ unit. Surprisingly, the NH₂-group participates in the formation of NH?···?Cl hydrogen bonds instead of the formation of (NH?···?N3_(pyrimidine))₂ synthon, which is common for N-heteroaromatic compounds containing the NH₂-group in the α-position to aza-atom. These hydrogen bonds together with Cu?···?Cl contacts result in the formation of a 3-D-structure.     

Crystal Structure and Theoretical Energy Gap of 2-(2-((4-(Pyridin-2-yl)pyrimidin-2-yl)disulfanyl)pyrimidin-4-yl) pyridinium Hexafluorophosphate

The crystal structure of 2-(2-((4-(pyridin-2-yl)pyrimidin-2-yl)disulfanyl)pyrimidin-4-yl)pyridinium hexafluorophosphate was obtained by X-ray single-crystal diffraction. This molecule crystallizes in monoclinic P2/c space group with a=6.219(1), b=13.103(2), c=13.059(2) ?, β=97.567(2)°, Z=2, the final R=0.0525 and w R=0.1434. The title compound was prepared successfully from 1,2-bis(4-(pyridin-3-yl)pyrimidin-2-yl)disulfane(BPPD). TD-DFT computational studies on energy gaps and UV-Vis spectra of BPPD and the title compound have been carried out for comparisons. The resultant HOMO-LUMO gap of the BPPD compound is 4.45 e V, while that for the corresponding hexafluorophosphate salt is much smaller at 2.46 e V, which are in agreement with their UV-Vis absorptions.     

Synthesis,structural characterization,molecular docking,and urease inhibition studies of dinuclear cobalt(II) complexes derived from 3,5-bis(pyridin-2-yl)-4-amino-1,2,4-triazole

Two dinuclear Co(II) complexes, [Co₂(L)₂(EtOH)₄]·4ClO₄ (1) and [Co₂(L)₂(H₂O)₂(NO₃)₂]·2NO₃ (2) (L?=?4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole), have been obtained and characterized by IR, elemental analysis, and single-crystal X-ray diffraction analysis. The stabilization of their crystal lattices is maintained by strong H-bonds between counterions and host framework, which lead to various supramolecular architectures. The urease inhibitory properties of 1, 2, and L were investigated, where the two complexes revealed strong urease inhibition activities. Docking simulations of 2 have been performed with H. pylori urease (PDB code: 1E9Z) to rationalize their binding models.