Chemical Papers最新文献

Inhibition of EGFR tyrosine kinase (TK) activity is considered a promising therapeutic strategy for cancer treatment. Type I and II EGFR TK inhibitors bind the ATP-binding site, while type III and IV inhibitors target an allosterically sensitive pocket proximal to the ATP-binding site present in a variety of kinases. The current work aimed to synthesize new biphenyl-containing derivatives that were predicted to act as EGFR tyrosine kinase allosteric site inhibitors based on molecular docking studies. A novel series of 4'-hydroxy-[1,1'-biphenyl]-4-carbohydrazide derivatives (W3–W15) were synthesized and characterized using infrared, ¹HNMR, and ¹³CNMR spectroscopy, and high-resolution mass spectrometry. Compound W4 had a favorable pharmacophore-fit score suggesting that it may have biological activity similar to the reference 6DUK (EGFR with bound allosteric inhibitor). Compound W4 exhibited a favorable ΔG score against EGFR TK allosteric site indicating a high likelihood of compound-receptor complex formation, and it was predicted to be non-carcinogenic and non-irritant. Compounds W3–W7 demonstrated selective cytotoxicity towards the A549 lung cancer cell line as compared to the other two cell lines investigated (HCT-116 colorectal and HeLa cervical cancer cells). Compound W4’s IC₅₀ value against A549 cancer cells (0.4 µM) was 20-fold lower than Erlotinib’s (7.3 µM). Finally, compound W4 targeted EGFR TK in the A549 cell line, causing cell cycle arrest at the G2/M phase and activating the extrinsic apoptotic pathway. In conclusion, compound W4 is a promising EGFR tyrosine kinase allosteric inhibitor that is worthy of further investigation.

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The Cu-catalysed azide-alkyne cycloaddition (CuAAC) reaction, also known as the “click” reaction, is a powerful tool in organic synthesis due to its high efficiency, regioselectivity, and mild reaction conditions. However, the use of homogeneous copper catalysts often leads to challenges like separation and disposal, limiting their applicability in industrial settings. This study aimed to develop a novel heterogeneous catalyst utilizing NiO/Cu₂O/CuO nanocomposites (NCs) for the selective and efficient synthesis of 1,4-disubstituted-1,2,3-triazoles via the click reaction. NiO/Cu₂O/CuO NCs were prepared by a simple co-precipitation method. The catalytic activity of the prepared NCs was evaluated for the one-pot, three-component click reaction between benzyl bromide analogues, sodium azide, and phenyl acetylene under various conditions: ambient temperature, thermal heating, and microwave irradiation. The reaction progress was monitored by TLC, and the products were isolated and characterized by SEM, FTIR, XRD, and XPS. The NiO/Cu₂O/CuO NCs exhibited superior catalytic performance compared to Cu₂O/CuO nanoparticles (NPs). They facilitated the exclusive formation of the desired 1,4-isomer under all tested conditions. Notably, under microwave irradiation, the NiO/Cu₂O/CuO NCs delivered significantly higher yields (89–96%) compared to Cu₂O/CuO NPs (76–82%) for diverse triazole compounds. Characterization confirmed the successful synthesis of the NCs and the purity of the triazole products. Utilizing water as the solvent under microwave irradiation offered several advantages, including faster reaction rates, higher yields, efficient product isolation, and excellent recyclability of the catalyst. This study demonstrates the effectiveness of NiO/Cu₂O/CuO NCs as a novel heterogeneous catalyst for the selective and efficient synthesis of 1,4-disubstituted-1,2,3-triazoles. The simple and efficient method, coupled with the advantages of water as a solvent and microwave-assisted heating, presents significant potential for various applications in organic synthesis and beyond.

Mixed-ligand complexes of Pd(II) and Pt(II) with 2H-benzo[e][1,3] oxazine-2,4(3H)-dione (HBzoxe), tertiary phosphines (dppe, dppp, dppf and Ph₃P), 2,2′-bipyridine (Bipy) and 1,10-phenanthroline (Phen) have been synthesized and characterized by molar conductance measurements, elemental analysis, IR and NMR (¹H, ¹³C and ³¹P) spectroscopy. In addition, the antimicrobial activity assay studies. The results showed that the HBzoxe ligand behaves as a bidentate chelation ligand through the O and N atoms in [M(Bzoxe)₂] {M^II = Pd(1) and Pt(2)} complexes, whereas it acts as monodentate ligand through the oxygen atom in complexes (3–14) to afford a square planner geometry around Pd(II) and Pt(II) for all of the complexes. All of the complexes were moderately active on all the bacteria tested (Staphylococcus aureus and Escherichia coli). Hirshfeld surface analysis was carried out to investigate the cooperative non-covalent supramolecular interactions within the various complexes.

This study comprehensively investigates the interactions between a new chromene derivative, 8-methoxy-3-nitro-2-(4-methoxyphenyl)-2H-chromene (MMNC), and DNA using a combination of experimental and computational techniques. MTT assays demonstrated MMNC’s potent anticancer activity against various cell lines, with lower IC50 values than the clinically used drug 5-fluorouracil. Spectroscopic techniques including circular dichroism, dynamic light scattering, UV–visible absorption, and fluorescence quenching experiments revealed that MMNC interacts with DNA at its minor groove without significantly altering its overall structure. The binding constant (Ka) was determined to be 3.09 × 10³ M⁻¹, indicating moderate groove binding. Molecular docking simulations supported the experimental findings, showing MMNC favorably binds to the DNA minor groove with a docking score of − 2.5 kcal/mol and binding free energy of − 26 kcal/mol. DFT studies provided insights into MMNC's electronic properties, with a HOMO–LUMO energy gap of 3.14 eV suggesting good reactivity. ADME/Tox analysis confirmed MMNC's drug-like properties, with no violations of Lipinski's rule of five or Jorgensen's rule of three. The comprehensive results demonstrate MMNC's promising potential as an anticancer agent and provide a foundation for rational design of improved chromene-based drugs.

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An electrochemical analysis of Hydroquinone (HDQ) and Catechol (CTL) was analyzing in a 0.2 M phosphate buffer solution (PBS) using a modest constructing electrochemically polymerized (EP) L-Alanine (ALN) modified carbon nanotube paste electrode (EP(ALN)MCNTPE). The electrochemical, structural, resistive, and conductive properties of both the EP(ALN)MCNTPE and bare carbon nanotube paste electrode (BCNTPE) surfaces were studied by cyclic voltammetry (CV), Differential pulse voltammetry (DPV), scanning electron microscopy (SEM) and electrochemical impedance Spectroscopy (EIS) techniques. The EP(ALN) presented electrode surface exhibits significantly enhanced peak currents compared to BCNTPE. The optimizing experimental parameters, including PBS in pH, scan rate and concentration variation, also constructed to achieving high selectivity and sensitivity for the analysis of HDQ. The oxidation and reduction peak currents of HDQ exhibited improvement with increasing concentrations ranging from 0.2 µM to 4.0 µM. The achieved lower limit of detection (LOD) and lower limit of quantification (LOQ) were 0.174 µM and 0.582 µM, alone and it shows good analytical responses. The EP(ALN)MCNTPE shows good stability, reproducibility, and repeatability for HDQ. The electrochemically developed sensor proved applicable for both quantitative and qualitative analysis of HDQ in a cosmetic sample.

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This research aimed to examine the interplay among carotenoids, total polyphenols, and indole alkaloids for the discovery of new bioactive compounds using “simplex-centroid” designs and response surface methodology (RSM). The antioxidant (AOA) and anti-inflammatory (AIA) activities of mixtures containing different proportions of each compound were evaluated by measuring the percentage inhibition of oxidation and spontaneous inflammation. The results showed that the highest AOAs were obtained with different mixtures of polyphenols, indole alkaloids, and carotenoids. The DPPH test revealed that a mixture of 16.94% polyphenols and 83.05% indole alkaloids produced the best results, whereas, for the ABTS test, 100% polyphenols gave the best results. The FRAP assay showed that the best-performing mixture was composed of 85.96% carotenoids and 14.03% polyphenols, with an IC₅₀ of 8.85 ± 1.17 μg/mL. In contrast, the most potent AIA was obtained with 100% carotenoids. Model validation tests were performed and showed that the experimentally observed values for AOA and AIA were not significantly different from the values estimated by the fitted models. The results also showed that the RSM model can be used to estimate the behavior of mixed compounds in the development of new functional ingredients or the discovery of new bioactive compounds with pharmacological properties. Finally, the results also suggested that there is a good correlation between several AOA and AIA assays, which makes natural substances combining these biological activities particularly interesting.

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The assessment of two diamine derivatives, TMD and IPDA, as corrosion inhibitors for aluminium in hydrochloric acid (HCl) at concentrations of 0.2 M, 0.3 M, and 0.4 M. (4S)—2,2,4-trimethyl hexane-1,6-diamine (TMD) and (1R,3R)-3-(amino methyl)-3,5,5-trimethyl cyclohexane-1-amine (IPDA) are verified for their ability to inhibit corrosion of Al in acidic conditions. The evaluation is conducted using electrochemical impedance spectroscopy (EIS), potentiodynamics polarization (PDP), and gravimetric methods. The inhibitors' effectiveness depends on their concentration (ranging from 20 to 50 mM) and molecular structure. Because TMD has more anchoring functional groups, it had the best inhibitory efficacy, reaching a maximum of 98.3% at 50 mM concentration. It is looked into how temperature (313–333 K) affects corrosion behaviour. As per Langmuir’s adsorption isotherm, the temperature probably influences the ability of inhibitors to adsorb on the surface of aluminium, pointing to a monolayer adsorption mechanism. Calculated and described are the thermodynamics activation factors for the dissolution process of Al in both inhibited along uninhibited solutions. The stability of the inhibitor-Al contact and the reaction kinetics are revealed by these characteristics. The creation of a protective covering on the Al surfaces was validated by surface investigation techniques such as atomic force microscopy, scanning electron microscopy, and energy-dispersive X-ray (EDX) analysis, demonstrating the inhibitors’ efficacy in preventing corrosion. The inhibitors’ molecular chemical makeup as well as the degree of inhibitory efficacy is correlated in theoretical investigations employing molecular dynamics simulations and density functional theory. Theoretical calculations shed additional light on the adsorption mechanism.

Theophylline is a kind of methyl xanthine derivative that can be found in various foods and is a widely used bronchodilator drug. It is significant to detect theophylline by a sensitive, low-cost, and rapid determination technique. In the investigation, zinc oxide (ZnO) nanoparticles and multiwalled carbon nanotubes (MWCNTs) co-modified carbon paste electrode (CPE) was fabricated by a simple procedure and then was successfully applied to determine theophylline. The electrochemical behavior of the modified electrode was explored using cyclic voltammetry (CV) and differential pulse voltammetry (DPV). Compared with the bare CPE and MWCNTs/CPE, the ZnO-modified MWCNTs/CPE electrode (ZnO/MWCNTs/CPE) exhibited good promoting effect on the electrochemical reaction of theophylline. Under the optimized experimental statuses, the differential pulse voltammetric peak currents can be used to detect TP, since it had a linear relationship with the theophylline concentration in the range of 3.3 × 10⁻⁷–1.3 × 10⁻⁴ M. The detection limit is 8.3 × 10⁻⁸ M (S/N = 3), and the sensitivity is 0.12048 μA μM⁻¹. Furthermore, the fabricated sensor shows high sensitivity, good selectivity, and good stability toward theophylline determination. Finally, we used the prepared electrode as an actual sample to the determination of theophylline in pharmaceutical formulations.

Herein, superhydrophilic polyester textiles were fabricated via plasma modification with a view to their application in the separation of oil–water mixtures. The research delved into the impact of fabric treatment and variations in grammage, including 77, 104, and 132 g/m² on separation performance and flux. The surface characteristics of the prepared polyester textiles were assessed through scanning electron microscopy (SEM) and energy-dispersive X-ray spectroscopy (EDS) analyses. Additionally, the antifouling properties and reusability of both fabrics without treatment and treated fabrics were examined. Notably, employing a five-layer treated fabric substantially improved separation efficiency up to 99.78%, and even after 5 cycles, it remained at 91.80%, attributable to the enhanced hydrophilicity conferred by APP treatment. In addition, after 20 abrasion cycles, the oil contact angle (OCA) of the five-layer treated polyester fabric decreased by 36 °.