Journal of the Iranian Chemical Society最新文献

In this report, we developed a series of novel fused imidazo[1,2-a]pyridine-benzo [4,5]isothiazolo[2,3-c] [1,2,3]triazoles derivatives in a one-pot method under microwave conditions by using iodoalkyne, sulfonamide, and triflyl azide. This method enables the synthesis of fused 1,2,3-triazoles via Cu(I)-catalysed cycloaddition and C-C bond coupling in shorter reaction times and with good to excellent yields. Later, antimicrobial activity was evaluated for the synthesized compounds (6a-6n) against three Gram-positive bacterial strains, B. subtilis, S. aureus, and S. epidermidis. Among all compounds, 6k has shown ≈ 2-fold more potent against the three tested bacterial strains with MIC values 1.56 ± 0.23 to 3.12 ± 0.43 µg/mL. Similarly, compound 6 L has shown ≈ 2-fold more potent against S. aureus and S. epidermidis with IC₅₀ values 3.12 ± 0.47 and 3.12 ± 0.38 µg/mL, and equipotent against B. subtilis with IC₅₀ value 3.12 ± 0.54 µg/mL. Compounds 6 g and 6n have shown equipotent activity against B. subtilis and S. aureus, comparable to standard dicloxacillin. Later, more potent compounds were screened for their in silico molecular docking studies against Penicillin-binding protein, and compounds 6f, 6k, and 6 L have shown similar H-bonding interactions with dicloxacillin, and these three compounds have shown the highest binding energies with − 8.04 to -8.97 Kcal/mol.

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SAR of target fused 1,2,3-triazoles (6a-6n)

A BiMgFeO₄/activated carbon (BiMgFeO₄/AC) composite was synthesized via a glycine-assisted self-combustion method and evaluated as an adsorbent for the removal of methyl orange (MO) and methyl green (MG) from aqueous solutions. The structural and textural properties were investigated using SEM, FTIR, XRD, and N₂ adsorption–desorption analyses. SEM observations revealed a porous microstructure favorable for dye diffusion, while BET analysis confirmed a mesoporous structure with an average pore diameter of 7.54 nm. FTIR analysis confirmed the presence of characteristic metal–oxygen bonds and surface functional groups and XRD patterns evidenced the presence of Fe₃O₄, MgO, and Bi₂O₃ phases, confirming the successful formation of the composite. Adsorption experiments examined the effects of temperature, contact time, initial dye concentration, and adsorbent dose. Equilibrium data were well described by both Freundlich and Langmuir isotherm models. The maximum adsorption capacities reached 196.08 mg g⁻¹ for MO and 192.31 mg g⁻¹ for MG at 298 K. Kinetic studies showed that the adsorption process followed a pseudo-second-order model and reached equilibrium within 120 min. Weber–Morris intraparticle diffusion and Boyd models revealed distinct mass-transfer mechanisms for the anionic (MO) and cationic (MG) dyes. Thermodynamic parameters confirmed that adsorption was spontaneous and exothermic, governed predominantly by physical interactions. Overall, the BiMgFeO₄/AC composite shows good adsorption performance for dye removal, offering a promising strategy for wastewater remediation.

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Calibration is an integral part of quantitative chemical analysis which can be followed in either a classical or inverse style. While calibration methods have been investigated since the early days of analytical chemistry, they have been periodically refreshed and modified over the years. As a part of this ongoing progress, a novel generic calibration scenario has been implemented to treat partial knowledge of the concentration profiles, offering an alternative approach to performing ILS through a regularization process. The primary feature of the proposal is to design a calibration set supplementing the analyte’s concentration with artificial vectors of random numbers to compensate for any potential interferent contributions. In this way, the new inverse calibration, titled Random Augmented Inverse Least Squares (RAILS) uses only the concentration of the analyte and the number of n-1 pseudo-components with random concentration profiles must be optimized. Monte Carlo Cross-Validation (MCCV) was employed to optimize the urgent number of dummy concentration vectors required during RAILS and it was tested across several simulated and real experiments from different spectroscopic schemes.

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Green-synthesised silver nanoparticles prepared using plant extract have great significance in medicine. In the present study, a simple, and eco-friendly procedure was employed for preparing silver nanoparticles (AgNPs) using Alternanthera sessilis leaf extract. The average hydrodynamic diameter of AgNPs was determined as 185 nm with a zeta potential value of -19.3 mV. Under the transmission electron microscope (TEM), AgNPs appeared to possess a spherical structure. UV-visible spectrum of AgNPs showed maximum absorption at 420 nm. AgNPs have proven to exhibit antibacterial activity against Escherichia coli. The viability of NIH3T3 cells incubated with AgNPs was assessed using MTT assay, which revealed the cytocompatible nature of the nanoparticles. Haemolytic assay carried out using human red blood cells proved the haemocompatible nature of AgNPs. Prolonged exposure to triethylamine (TEA) can lead to adverse health effects. Developing a simple method for TEA detection will be significant, as it is extensively used for various industrial applications. In the present study, a spontaneous change in colour (yellow to dark brown) of AgNPs solution was recorded, when the nanoparticles were added to different concentrations (0.01 mM – 0.1 mM) of TEA.

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Catalytic applications of nanoparticles (NPs) for the removal of toxic dyes from wastewater has motived researchers to synthesize different metal NPs employing different methods under different conditions. In current study, nickel oxide NPs (NiO NPs) have been successfully synthesized via green method using Nigella sativa (black seeds) extract as reducing and stabilizing agent. A comparative study has been conducted between the two samples i.e. uncalcined (S1) and calcined (S2) NiO NPs. Synthesized NiO NPs were characterized by different analytical techniques UV–Vis, FTIR, zeta potential, particle size analyzer, photoluminescence, XRD and SEM. Results (280 to 350 nm with a minor shift) of UV–Vis spectroscopy and FTIR analysis (Ni–O band at 650 cm⁻¹) confirmed synthesis of the NPs in both the samples. Intensity peaks in FTIR spectrum of S2 sample are stronger that indicate enhanced crystallinity. The crystallite size of NiO NPs was 6.55 nm calculated using XRD spectrum data and SEM images reveled rod like structure of NiO NPs with uniform distribution of particles. The optical energy band-gap was found to be about 5.21 eV for S1 sample while S2 sample exhibited reduced band-gap of 3.56 eV. The photocatalytic potential of NiO NPs was investigated under sunlight through the decolorization reaction of methylene blue (MB) and congo red (CR) dye. The synthesized calcined NiO NPs exhibited an excellent catalytic degradation of MB and CR dye (72% and 62% respectively) in lesser time as compared to uncalcined NPs. Current study recommends post synthesis treatments such as calcination of the NPs to achieve their maximum efficiency towards pollutant degradation.

The applicability of chemically treated potato peel (MPP) as a sustainable biosorbent for the removal of Pb²⁺ ions and methylene blue (MB), investigated independently in single-solute systems, from aqueous media is explored in this study. Optimal Pb²⁺ adsorption was observed at an initial concentration of 800 mg/ L using 0.15 g of MPP after 120 min of contact at pH ≈ 6.0, whereas methylene blue exhibited its highest removal efficiency at a lower initial concentration of 400 mg/ L under comparable batch conditions. The sorption performance was assessed in 25 mL solution volumes for each contaminant separately, yielding maximum adsorption capacities of 370.37, 416.67, and 476.19 mg/g for Pb²⁺ at 298, 308, and 318 K, respectively, and 181.81, 227.27, and 285.71 mg/g for MB. Kinetic analyses showed that both systems were well described by the pseudo-second-order model, indicating the involvement of surface-controlled adsorption processes. Furthermore, thermodynamic evaluations demonstrated that the processes were endothermic and occurred spontaneously. These findings substantiate the potential of MPP as a low-cost, renewable, and efficient adsorbent for wastewater purification targeting toxic metals and synthetic dyes when evaluated individually under comparable experimental conditions.

A series of novel polyhydroxy-conjugated pyrrolidine derivatives was designed, synthesized, and evaluated for antiglycation, antioxidant, and α-glucosidase potential to mitigate hyperglycemia-associated complications. Structural elucidation of the synthesized analogues was performed using spectroscopic techniques, and in vitro biological potential was assessed using UV-visible spectroscopy assays. Among the synthesized derivatives, compound 4a emerged as the potent candidate, significantly reducing the formation of advanced glycation end products (AGEs), by significant inhibition of fructosamine (IC₅₀ = 216.29 ± 7.06 µM), protein carbonyls formation (IC₅₀ = 155.13 ± 1.40 µM), thiol oxidation (IC₅₀ = 93.50 ± 7.12 µM), and Congo red binding (IC₅₀ = 156.52 ± 1.13 µM), outperforming the standard drug (Rutin). Furthermore, compound 4a also demonstrated superior α-glucosidase inhibition (IC₅₀ = 137.67 ± 16.88 µM) compared to rutin (IC₅₀ = 274.96 ± 0.80 µM). Additionally, Compounds 4a, 4b, and 4f exhibited superior free-radical scavenging activity, underscoring their potential to reduce reactive oxygen species associated with glycation. Molecular docking simulations against the α-glucosidase (PDB ID: 3A4A) revealed that strong binding affinity mediated by extensive hydrogen bonding with key amino acid residues, including Asp69, Glu277, Asp352, Arg442, and Gln29. Overall, these finding highlights polyhydroxy-conjugated pyrrolidine derivatives as promising antiglycation scaffolds for the development of therapeutic targeting glycation and postprandial hyperglycemia.

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Polyhydroxy-conjugated pyrrolidine derivatives were synthesized, characterized, and evaluated for in vitro antioxidant, antiglycation, and glycolytic enzyme inhibition assays. Notably, compound 4a emerged as the most promising molecule, a finding further supported by an in-silico study.

In the context of research into known synthetic possibilities under the conditions of condensation reaction, based on cobalt salt (Co(CH₃COO)₂•4H₂O) with 3-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H-pyrazol-4-yl)diazenyl)pentane-2,4-dione, metal-complex was synthesized. To assess its interactions with biological targets, a single-crystal X-ray diffraction structure analysis were conducted. It has been revealed that independent part of the unit cell of the cobalt(II) complex contains one complex molecule of composition C₃₂H₃₄N₈O₆Co(II), one molecule of acetic acid anion and five molecules of water of crystallization. All atoms are in a general position. The four O atoms in the equatorial plane around the Co atom form a slightly distorted square-planar arrangement with an average Co-O bond length of 1.888 Å, and the slightly distorted octahedral coordination is completed by the two N atoms of the in the axial positions. Each Co(II)-complexes contain two independent molecules of C₁₆H₁₇N₄O₃. This molecule has pentagonal and hexagonal cyclic fragments. This complex is effective inhibitor of the α-glycosidase, butyrylcholinesterase (BChE), cytosolic carbonic anhydrase I and II isoforms (hCA I and II), and acetylcholinesterase enzymes (AChE) with Ki values of 1.93 ± 0.38 µM for hCA I, 1.85 ± 0.12 µM for hCA II, 6.31 ± 0.47 µM for α-glycosidase, 39.54 ± 8.18 µM for BChE, and 49.85 ± 15.72 µM for AChE, respectively. Afterwards, the interactions of the molecules against various proteins that are structure of α-galactosidase (α-Gly) (PDB ID: 1R47), carbonic anhydrase I (hCA I) (PDB ID: 2CAB), carbonic anhydrase II (hCA II) (PDB ID: 3DC3), acetylcholinesterase (AChE) (PDB ID: 4M0E), and butyrylcholinesterase (BChE) (PDB ID: 5NN0) were examined and their activities were compared.

Mechanochemistry is rewriting the rules of organic synthesis, transforming once energy hungry, solvent intensive transformations into rapid, selective, and sustainable processes driven by mechanical force. By harnessing mechanical energy, typically through ball milling or manual grinding, this approach enables the formation of chemical bonds without the need for conventional thermal or solution based activation. Over the past two decades, mechanochemistry has evolved from a niche curiosity to a mainstream methodology in synthetic organic chemistry, delivering improved reaction efficiency, reduced environmental impact, enhanced selectivity, and remarkable scalability. This review unveils how solvent free grinding has become a powerful engine for complex molecular construction, turning the traditional mortar and pestle practice into high efficiency mechanized milling. We present the comprehensive and critical survey to date, mapping the mechanistic foundations, synthetic versatility, and green chemistry benefits of mechanochemical transformations. Coverage spans C–C, C–N, and C–X bond forming reactions, functional group modifications, and the synthesis of biologically active and pharmaceutically important molecules, from classic rearrangements to cutting edge multi step cascade processes. Special emphasis is placed on reaction design, mechanistic insights, catalyst innovation, and the growing integration of mechanochemical strategies in pharmaceutical manufacturing. This transformation underscores mechanochemistry’s role not merely as an alternative, but as an upgraded synthetic paradigm poised to shape the future of organic chemistry in the twenty-first century.

Aza-Michael addition reaction is one of the most extensively used synthetic pathways for the C-N bond formation in organic transformation research involving the use of innovative and environmentally benign reaction media. In the present work, we have developed a high-yielding green protocol for the Aza-Michael addition reaction of N-heterocycles and alkenes having electron-withdrawing groups (EWGs) using various recyclable acidic DES as catalysts prepared in a 1:1 molar ratio, thus avoiding the use of alternative acid additives. The reaction conditions have been optimized in terms of DES used, DES loading, time of reaction and temperature, wherein the outcome is a function of the acidity of the components of DES. The optimized conditions for the reaction using ChCl:p-TSA as the model catalyst were found to be 1.6 mmol DES loading, 45 °C temperature and 1.5 h reaction time, giving isolated product yields of up to 95%.

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General scheme for Aza-Michael addition reaction. Aza-Michael addition of N-heterocycles and alkenes using green methodology. Environmentally benign Choline based acidic deep eutectic solvents. Mild reaction conditions. Efficiently recyclable catalysts with easy post reaction workup. High yield and purity of Aza-Michael Adducts.