Journal of Molecular Structure最新文献

{"title":"Dibenzoxanthene-β-lactam hybrids as potential antioxidant and anticancer agents: Synthesis, biological evaluation, and docking study","authors":"","doi":"10.1016/j.molstruc.2024.140455","DOIUrl":"10.1016/j.molstruc.2024.140455","url":null,"abstract":"<div><div>In this study, we designed and synthesized a series of <em>β</em>-lactam compounds bearing 14-phenyl-14H-dibenzo[<em>a,j</em>]xanthene moiety attached to the N-1 position of the <em>β</em>-lactam ring through a [2 + 2] cycloaddition process. All the synthesized compounds have been characterized by elemental analysis, Fourier-transform infrared (FT-IR) and nuclear magnetic resonance (¹H NMR and ¹³C NMR) spectral analysis. These derivatives were evaluated for their anticancer and antioxidant activities. The <em>in vitro</em> anticancer activity of new compounds was examined against MCF-7 (breast cancer), HepG2 (liver hepatocellular carcinoma), and TC-1 (mouse lung epithelial) cell lines by 3-(4, 5-dimethylthiazolyl-2)-2, 5-diphenyltetrazolium bromide (MTT) assay. Notably, compounds <strong>4c, 4e</strong> and <strong>4 g</strong> demonstrated significant anticancer activity against TC-1 cell line. Additionally, compounds <strong>4c, 4f</strong> and <strong>4 g</strong> exhibited promising levels of efficacy against the MCF-7 cell line. The diphenylpicrylhydrazyl (DPPH) radical scavenging assay indicated that <strong>4</strong> <strong>h</strong> and <strong>4i</strong> are more potent antioxidant agents than the Vitamin C, while <strong>4a, 4b, 4c</strong>, and <strong>4j</strong> exhibited moderate antioxidant capabilities. Furthermore, the docking simulations are consistent with the biological assay results, indicating that the hybrids may bind to protein targets through hydrogen bonding and other nonvalent interactions.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":null,"pages":null},"PeriodicalIF":4.0,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142553892","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"In silico studies of thiazole derivative towards its potential use against SARS-CoV-2: An intuition from an experimental and computational approach","authors":"","doi":"10.1016/j.molstruc.2024.140475","DOIUrl":"10.1016/j.molstruc.2024.140475","url":null,"abstract":"<div><div>The <em>N-(4-methoxyphenyl)-4-phenylthiazole-2-carboxamide</em> (<strong>TT7</strong>) obtained via cyclization of <em>methyl 2-((4-methoxyphenyl)amino)-2-oxoethanedithioate</em> with ɑ-haloketone and then characterized by ¹H NMR and ¹³C NMR spectroscopy, and single crystal X-ray diffraction method. Weak intermolecular interactions like C<img>H…O, C<img>H…π, C<img>O…π, and π…π interactions help to stabilize the compound <strong>TT7</strong>. The weak interactions formed in the solid structure of the compound <strong>TT7</strong> were meticulously investigated using theoretical approach like Hirshfeld surface analysis using crystallographic information file (.cif). Further, the density functional theory calculations have been performed to obtain the optimized geometry of the structure, and to explore the electronic properties of the molecule. The charge distribution on the molecular surface is analyzed by the molecular electrostatic potential (MEP) map. QTAIM and RDG analyses were done to explore the weak interactions (intramolecular) in the compound <strong>TT7</strong> in the gaseous phase. The compound <strong>TT7</strong> displayed good <em>in silico</em> results against SARS-CoV-2 main protease. Molecular docking study on SARS-CoV-2 virus major protease (PDB IDs: 6LZE and 6LU7) shows higher docking scores. Molecular dynamics simulations confirmed the inhibitory action of the newly synthesized compound (TT7). The binding free energy and contributed energies were determined using the MM-GBSA technique. The 6LU7-ligand complex has the highest binding free energy, with considerable contributions from covalent and van der Waals interactions.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":null,"pages":null},"PeriodicalIF":4.0,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142572168","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"NNN type pincer Pd (II) complexes of pyridine-2,6-dicarboxamides: Catalytic activity and supramolecular formation","authors":"","doi":"10.1016/j.molstruc.2024.140462","DOIUrl":"10.1016/j.molstruc.2024.140462","url":null,"abstract":"<div><div>Pyridine-2,6-dicarboxamide, NNN pincer type pro-ligands, and their palladium complexes were synthesized. The prepared pro-ligands and complexes were characterized with several characterization techniques (FT-IR, ¹H NMR, ¹³C NMR, and UV–vis analyses). The molecular structure of the acetonitrile-<em>N</em>²,<em>N</em>⁶-<em>bis</em>(2-bromophenyl)pyridine-2,6-dicarboxamidopalladium(II) complex has been determined by single crystal XRD measurement. This complex contains intramolecular and intermolecular H-bonds, C<img>H⋅⋅⋅π and face-to-face π⋅⋅⋅π interactions. In addition, two synthons were found in the crystal lattice that have been generated through hydrogen-bond interactions. Homo-synthons (<span><math><mrow><msubsup><mi>R</mi><mn>2</mn><mn>2</mn></msubsup><mrow><mo>(</mo><mn>12</mn><mo>)</mo></mrow></mrow></math></span>), which forms through C<img>H⋅⋅⋅O intermolecular interactions (2.816 Å for C15<img>H15⋅⋅⋅O1 and 2.603 Å for C13<img>H13⋅⋅⋅O2) and hetero-synthons (<span><math><mrow><msubsup><mi>R</mi><mn>2</mn><mn>1</mn></msubsup><mrow><mo>(</mo><mn>8</mn><mo>)</mo></mrow></mrow></math></span>), that generated via C<img>H⋅⋅⋅N intermolecular interactions (C21<img>H21C⋅⋅⋅N4, 3.439 Å). Furhermore, homo-synthons (<span><math><mrow><msubsup><mi>R</mi><mn>3</mn><mn>3</mn></msubsup><mrow><mo>(</mo><mn>11</mn><mo>)</mo></mrow></mrow></math></span> and <span><math><mrow><msubsup><mi>R</mi><mn>2</mn><mn>2</mn></msubsup><mrow><mo>(</mo><mn>9</mn><mo>)</mo></mrow></mrow></math></span>) through intermolecular contacts were determined between the palladium complex and the acetonitrile molecules. Furthermore, a quantitative analysis of the noncovalent interactions within the structure was performed using Hirshfeld surface and two-dimensional fingerprint plot analyses. The three-dimensional arrangement of the crystal packing was assessed during the energy-framework calculations, revealing that the electrostatic energy framework had a considerable influence on the dispersion energy framework. The [PdL⁵] complex provided a conversion of more than 98 % and a yield of more than 98 % in the shortest time among other catalysts, in which the Suzuki–Miyaura C<img>C cross-coupling reaction (SMR) was carried out with the 4-bromotoluene substrate. The activity of [PdL⁵] complex was then examined in the reactions of two other substrates, 1-bromo-4-isobutylbenzene and 2-bromo-6-methoxynaphthalene. Although a yield of over 97 % and a conversion of over 97 % were observed in the reaction of 1-bromo-4-isobutylbenzene after two hours, the reaction of 2-bromo-6-methoxynaphthalene achieved complete conversion and a yield of over 99 % within just one hour.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":null,"pages":null},"PeriodicalIF":4.0,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142577945","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Pharmaceutical salt of isoniazid−orotic acid with optimized solubility, dissolution rate, and tabletability","authors":"","doi":"10.1016/j.molstruc.2024.140472","DOIUrl":"10.1016/j.molstruc.2024.140472","url":null,"abstract":"<div><div>Isoniazid (INH) is a first-line antitubercular drug characterized by its high solubility and rapid absorption following oral administration, which poses challenges in maintaining sustained therapeutic concentrations. To address this issue, we have developed a novel pharmaceutical salt of INH with orotic acid (OA). Single-crystal X-ray diffraction (XRD) analysis revealed that intermolecular proton transfer occurs between the carboxyl group of OA and the pyridine nitrogen site of INH, resulting in a salt comprising INHH⁺ cations and OA⁻ anions. Solubility and dissolution studies indicated that INH−OA exhibits significantly reduced solubility and decelerated intrinsic dissolution rate (IDR). Specifically, solubility reductions were observed to be 74.24% in pH 1.2 HCl solution and 90.29% in pH 6.8 phosphate buffer solution. The IDR of the salt was found to be 2.62% and 0.96% of that of pure INH in pH 1.2 and pH 6.8 aqueous media, respectively. Additionally, INH−OA demonstrated improved tabletability. These findings suggest that the formation of this salt significantly enhances the pharmaceutical properties of INH.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":null,"pages":null},"PeriodicalIF":4.0,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142539571","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Fourier transform infrared spectroscopy: A power full method for creating fingerprint of molecules of nanomaterials","authors":"","doi":"10.1016/j.molstruc.2024.140454","DOIUrl":"10.1016/j.molstruc.2024.140454","url":null,"abstract":"<div><div>The Fourier transform infrared spectroscopy (FTIR) technique is a very useful tool to determine bonding mechanisms in solids. This technique is essential for understanding the properties and behaviors of nanomaterials, which have applications across various fields including medicine, electronics, and environmental science. The FTIR spectra gives complete profile of specimen/sample thus showcasing a distinct molecular fingerprint that can be used to scan, screen and investigate the performance of samples for many different components. By analyzing FTIR Spectroscopy data, this paper aims to study the chemical composition, molecular interactions within nanomaterials, polymer matrices or other materials like membranes, composites, characterizing covalent bonding information and identify a molecule through the combination of all of the functional groups. For industrial purpose, FTIR spectroscopy is also used as a quality control measure wherein it provides the complete spectra of the product or raw material that an industry uses. The change in the composition of the material is denoted by studying the variations in the pattern of absorption bands/ spectra so obtained. Thus, FTIR can be significant in identifying and origin of any problem in any material typically by microanalysis. This paper presents the methodology, interpretation of results, providing insights into the efficiency of FTIR as a characterization tool and the importance of FTIR spectroscopy technique for creating the fingerprint of molecules of nanomaterials, and polymer matrices or other materials like membranes, composites. This review paper will be helpful for the beginners in the field of chemical application of nanomaterials and spectroscopy.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":null,"pages":null},"PeriodicalIF":4.0,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142539574","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Structural and theoretical insights into the influence of thiocyanate ligands on divalent metal complexes with terpyridine derivatives","authors":"","doi":"10.1016/j.molstruc.2024.140459","DOIUrl":"10.1016/j.molstruc.2024.140459","url":null,"abstract":"<div><div>Four complexes with terpyridine derivative, thiocyanate anion, and selected <em>d</em>-electron metals were studied. The obtained complexes of the formulation [M(ftpy)(SCN)₂(CH₃OH)]•DMF (<em>M</em> = Mn (<strong>1</strong>), Co (<strong>2</strong>), Ni (<strong>3</strong>)) and [Cu(ftpy)(NCS)₂]•H₂O (<strong>4</strong>), where ftpy = 4′‐(furan-2-yl)-2,2′:6′,2′′‐terpyridine, were characterized using FTIR and UV–Vis spectroscopies, magnetic studies, elemental analysis, and single crystal X-ray crystallography. All compounds crystallize in a triclinic crystal system with space group <em>P</em><span><math><mover><mn>1</mn><mo>¯</mo></mover></math></span> and <strong>1</strong>–<strong>3</strong> are isomorphous and isostructural. The effect of the modification of the terpyridine ligand and the presence of the thiocyanate ligand on the structure has been verified. Interesting dependence was found in the structure of compound <strong>4</strong>, where the two thiocyanate ligands are differently coordinated, one via N and the other via S, and the formation of complex dimers connected through hydrogen bonds is observed. The π-stacking interactions and the resulting solid-state architectures of compounds <strong>1</strong>–<strong>4</strong> were inspected through a combination of DFT calculations, QTAIM, and NCIPlot analyses, and the stability of the complexes was studied by UV–Vis spectroscopy in various solvents.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":null,"pages":null},"PeriodicalIF":4.0,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142539577","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Novel approaches to improving gas separation: Ionic liquids coated coke/ NH2-UiO-66-based mixed matrix membranes for CO2/N2 separation","authors":"","doi":"10.1016/j.molstruc.2024.140479","DOIUrl":"10.1016/j.molstruc.2024.140479","url":null,"abstract":"<div><div>Permeability and separation efficiency of mixed matrix membranes (MMMs) are two important aspects. Polymeric membranes offer excellent mechanical and physical properties; however, they have a low permeability. To enhance the permeability and separation performance of polyvinyl chloride (PVC) membranes, Cholinium amino acid-based (IL) were impregnated with activated coke/ NH_2-UiO-66 (Zr) (AC/MOF) composite and then IL@AC/MOF filler was incorporated into PVC matrix. FTIR spectroscopy, TGA, SEM, EDX, and Brunauer-Emmett-Teller (BET) surface area measurement were used to characterize the MMMs prepared. The porous structure of MMMs nanocomposites causes AC/MOF composite to effectively accelerate gas the diffusion in the PVC matrix. The permeability measurements for CO₂ and N₂ were made at 288.15, 298.15, 308.15, and 318.15 K at pressure 3 bar The outcomes indicates that the incorporation of the IL@AC/MOF filler increased the permeability of the PVC/AC/MOF MMMs compared to the pure polymeric membrane. The mixed matrix membranes exhibit superior gas separation performance, surpassing the 2008 Robson's Upper Bound.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":null,"pages":null},"PeriodicalIF":4.0,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142553989","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Interface-engineered Ni(Fe/Al)-LDHs/g-C3N4 nanosheets with metallic Fe/AlN bonds for efficient photocatalytic degradation of tetracycline hydrochloride","authors":"","doi":"10.1016/j.molstruc.2024.140470","DOIUrl":"10.1016/j.molstruc.2024.140470","url":null,"abstract":"<div><div>To improve the photogenerated electron–hole separation efficiency and the number of reactive oxygen species of g-C₃N₄ in visible light. Herein, an interface-engineered Ni(Fe/Al)-LDHs/g-C₃N₄ nanosheets with Fe/Al<img>N bonds were prepared, which shows highly enhanced photocatalytic degradation performance with excellent structural stability. The interfacial structure of g-C₃N₄ was precisely regulated by metal Fe/Al on the surface of layered double hydroxides (LDHs), which could form Fe/Al<img>N bonds as the interfacial charge transfer channels. In addition, the metal Ni and Fe/Al on the surface of LDHs nanosheets can furnish more photocatalytic active sites and interface synergy. The obtained 7 %NiFe-LDHs/g-C₃N₄ owns the degradation rate of 99.23 % for tetracycline hydrochloride (TCH) in visible light. This work highlights a rational interface engineering strategy for the formation of a composite structure with interface interaction for efficient photocatalysts.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":null,"pages":null},"PeriodicalIF":4.0,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142539134","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A naphthimide based fluorescent probe for the detection of thiophenols and its application in actual water and food","authors":"","doi":"10.1016/j.molstruc.2024.140473","DOIUrl":"10.1016/j.molstruc.2024.140473","url":null,"abstract":"<div><div>Thiophenol (PhSH) and its derivatives are widely employed as common industrial raw materials, while they also pose high toxicity for animals and aquatic organisms. Herein, a novel fluorescent probe <strong>P1</strong> was constructed, based on photo-induced electron transfer (PET) mechanism, using naphthimide as the fluorophore and 7-nitrobenzoxadiazole as the recognizing group. Probe <strong>P1</strong> exhibited an “Off-On” fluorescence recognition response to PhSH by nucleophilic substitution reaction. The probe displayed advantageous properties for the recognition of PhSH, including a chromogenic response, high selectivity, fast response (&lt; 90 s), and a large Stokes shift (150 nm). In addition, probe <strong>P1</strong> exhibited a good linear response to PhSH within the range of 0–9 μM, and the limit of detection (LOD) is 21 nM. Furthermore, probe <strong>P1</strong> has been successfully applied for the efficient and rapid PhSH detection in environmental water and actual food samples.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":null,"pages":null},"PeriodicalIF":4.0,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142553988","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Exploration of pyridine-thiazolidin-4-one: Synthesis, DFT study, UV–Vis/ fluorescence spectroscopy analysis, antibacterial evaluation and molecular docking","authors":"","doi":"10.1016/j.molstruc.2024.140465","DOIUrl":"10.1016/j.molstruc.2024.140465","url":null,"abstract":"<div><div>The synthesis of the objective pyridine-thiazolidin-4-one (<strong>DCPI-MBT</strong>) was involved <em>via</em> the Knoevenagel reaction between 2-((3,5-dichloropyridinyl)imino)thiazolidinone derivative <strong>1</strong> and 4-methylbenzaldehyde <strong>2</strong> over refluxing in acetic acid and sodium acetate. The confirmed structure of this hybrid was elucidated through detailed spectral analyses. A comparison was made between the density functional theory (DFT) configurations of the frontier molecular orbitals in both the gas and solvated ground state (S_o) and the solvated excited state (S₁). UV–Visible and fluorescence spectra of the thiazolidin-4-one derivative were obtained in DMSO, displaying a significant Stokes’ shift (<span><math><mrow><mstyle><mi>Δ</mi></mstyle><mover><mi>ν</mi><mo>¯</mo></mover></mrow></math></span>= 3136.81 cm⁻¹). The synthesized <strong>DCPI-MBT</strong> was established to see how well they killed different kinds of pathogenic microbes, such as bacteria, viruses, and fungi. These results demonstrate that the synthesized <strong>DCPI-MBT</strong> has a broad-spectrum antibacterial capability that is on par with or even superior to conventional treatments in certain instances. Moreover, molecular docking simulation was used to evaluate the bindings of the synthesized <strong>DCPI-MBT</strong> with a target protein (PDB: <span><span>1kzn</span><svg><path></path></svg></span>). The binding energies, RMSD values, kinds of interactions with amino acid residues, and interaction distances of the hybrids were determined based on their substituent changes. This study analyzed the pharmacokinetic profiles of newly <strong>DCPI-MBT</strong>, using SwissADME predictions to focus on their potential as therapeutic agents. The <strong>DCPI-MBT</strong> has the promising pharmacokinetic profile for future development as a therapeutic drug, with optimum solubility, bioavailability, and a favorable interaction profile with biological targets.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":null,"pages":null},"PeriodicalIF":4.0,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142539566","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}