Journal of the Iranian Chemical Society最新文献

In this paper, isatin-hydrazone was synthesized using SBA-Pr-N-Is-But-SO₃H as nanocatalyst via the two-component reaction of isatin with hydrazine hydrate in an expeditious reaction with high yield of production. The sensing properties were evaluated in EtOH: H₂O (1:9) for the different cation (K⁺, Ca²⁺, Na⁺, Cu²⁺, Zn²⁺, Cr³⁺, Mn²⁺, Co²⁺, Al³⁺, Pb²⁺, Ag⁺, Cd²⁺, Ni²⁺, Hg²⁺, and Mg²⁺). The obtained results revealed that these compounds could be applied as chemosensor for the sensitive detection of Hg²⁺ and Ag⁺ ions using UV–Vis spectroscopy and fluorescence spectroscopy, respectively. The detection limit was calculated to be 1.17 × 10^–6 M for Hg²⁺ ions and 1.4 × 10^–6 M for Ag⁺ ions. Also, isatin-hydrazone was treated with 4-flurobenzaldehyde to obtain 4-fluorobenzaldehyde-N-(2-oxo-1,2-dihydro-3H-indole-3-indole-3-ylidene)hydrazone which could sensitively select Hg²⁺ ions among different ions using fluorescence spectroscopy. The detection limit of the colorimetric sensor to detect the Hg²⁺ ions is 3.6 × 10^–6 M. At the end of the reaction, the nanocatalyst was recovered and reused.

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This study examined the adsorption ability of Ni(II) metal ions from aqueous solutions on a physically activated adsorbent of Posidonia oceanica seagrass (AC-PO), which is both economically and naturally available. The effects of pH, amount of adsorbent, concentration of nickel ions, temperature, and contact time, which are among the parameters affecting the adsorption of Ni(II) ions on AC-PO, were examined. The kinetic data fit well with the pseudo-second-order model. The adsorption of Ni(II) ions showed compliance with Langmuir, Freundlich, and D-R isotherms. The Langmuir model showed better representation of data (0.9993). The maximum adsorption capacity of AC-PO for nickel ions was 138.89 mg·g⁻¹.at 25 °C The thermodynamic parameters such as ∆G°, ∆H°, and ∆S° were calculated for the Ni(II) ion, and it was determined that the adsorption was spontaneous and endothermic. In qualitative chemical analysis by energy dispersive spectroscopy (EDS), it was found that there was ion exchange with adsorption of nickel ions on the AC-PO adsorbent. According to the results obtained from this study, it can be said that the adsorption ability of the AC-PO adsorbent is quite high in the removal of Ni(II) ions from aqueous solutions.

Nitrogen-containing heterocycles have been desirable targets for synthesis for many years because of their structural diversity and biological significance. Five-membered heterocyclic rings, or pyrazole, are a flexible starting point for the design of effective bioactive compounds and are widely used in medicinal chemistry, drug discovery, agrochemistry, coordination chemistry, and organometallic chemistry. Pyrazole derivatives have played an important role in heterocyclic chemistry and have been extensively studied owing to their ease of access, diversified chemical reactivity, and broad biological properties, including antibacterial, anti-inflammatory, anticancer, analgesic, anticonvulsant, anthelmintic, antioxidant, and herbicidal properties. Pyrazole nuclei are synthesized via a variety of methods, including the multicomponent approach, dipolar cycloaddition, cyclocondensation of hydrazine with a carbonyl system, heterocyclic system, and multicomponent approach. The current review is an attempt to understand the chemistry and medicinal importance of the pyrazole-containing marketed drugs reported to date, which will undoubtedly assist the scientific community in making further advances in the isolation and synthesis of pyrazole-based novel bioactive compounds.

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Zirconium doped cerium nanoparticles have been found to be an excellent heterogeneous catalyst for the one-pot multi-component reactions of Barbituric acid, aromatic aldehyde and malononitrile to yield the Pyrano(2,3-d) pyrimidine derivatives in aqueous media. The results showed that nanosized CeO₂ − ZrO₂ has a potential catalytic material for the synthesis of title compound. All the synthesized molecules were determined and characterised by chromatographic and spectroscopic (IR,¹H-NMR, ¹³C-NMR, HR-MS) analysis. The formation, size and morphology of the metal ions present in the material is confirmed by powdered X-ray diffraction (XRD), scanning electron microscopy (SEM) and transmission electron microscopy (TEM) techniques. The synthesised compounds have shown good to excellent cytotoxicity against human breast cancer cell line MDA-MB-453.

An analytical method is presented for determining the uranium concentration in water samples via energy-dispersive X-ray fluorescence (EDXRF) spectrometry after solid-phase extraction. For the preconcentration procedure, the 1-(-2-thiazolylazo)-2-naphthol (TAN) reagent was used to complex the analyte in the samples. After the percolation of the sample and retention of the complex on a C18 disk, analysis was performed directly on the solid phase via EDXRF. The pH, sample flow rate, and sample volume were analyzed in terms of the uranium extraction. Using a sample volume of 110.0 mL buffered at pH 6.5 and a flow rate of 1.0 mL min⁻¹, an enrichment factor (EF) of 645 was achieved, with a limit of detection of 1.5 μg L⁻¹. The relative standard deviation (RSD, %), calculated from replications of the experiment under recommended conditions (n = 10; 20 μg L⁻¹), was 10%. The results of the analyte addition and recovery tests varied between 98 and 117%. The accuracy of the method was verified via analysis of a water reference material, with no significant difference between the obtained values and the certified values (95% confidence level). The method was applied to groundwater, river water, and tap water samples collected in Caetité, Bahia, Brazil, and the results were compared with those obtained via inductively coupled plasma‒mass spectrometry (ICP‒MS). All the collected samples presented uranium concentrations below the acceptable maximum limit for drinking water samples.

A range of fused heterocyclic compounds are generated utilizing the crucial intermediary 2-cyano-N-(2,5-dioxopyrrolidin-1-yl) acetamide 4. Spectral analysis was executed to support the structures of the newly synthesized compounds, which is expected to have a potential biological activity. The antimicrobial activity of the recently synthesized compounds and their derivatives has been tested against B. subtilis, S. aureus, E. coli, P. aeruginosa, S. typhimurium, C. albicans, and A. niger, as reference antibiotics, ampicillin and mycostatin, were used against test bacteria and fungi, respectively. In general, the novel produced compounds demonstrated a good antibacterial action against the previously indicated pathogens.

A series of twelve conjugates 9a-c, 10a-c, 11a-c, and 12a-c based on naturally occurring neo- and isocryptolepines I and II were synthesized and characterized. The synthetic pathways involved nucleophilic substitution reaction of the preprepared amines 4a-c and 5a-c with 1-(4-bromobutyl)indole derivatives 8a and 8b, respectively, in aprotic solvent under heating. The structures of the synthesized conjugates were elucidated by FTIR, ¹H NMR, ¹³C NMR, and MS spectrometry and showed data consistence with the expected structures. The antiproliferative activity of 9a-c, 10a-c, 11a-c and 12a-c was evaluated against HepG-2 and HCT-116 cancer cell lines using normal cells and reference drug paclitaxel. The screening results revealed that 9b and 9c were the most active conjugates against HepG-2 and HCT-116 cancer cell lines with IC₅₀: 8.49, 9.52, 16.87, 21.75 µM, respectively, using paclitaxel as a reference drug. It is worth noting that 9b and 9c were more selective toward cancer cells versus normal Vero cells. To rationalize the anticancer activity and selectivity of 9b and 9c, we have performed molecular docking study against human topoisomerases I and II for better understanding of their anticancer activities in atomic level. Molecular docking studies revealed that the presence of planar indoloquinoline fused four rings and a flexible side chain pharmacophores together improve DNA-intercalation and inhibition of DNA-Topo isomerases activity.

To investigate the retention mechanism of N-nitrosodiethanolamine (NDELA) in liquid chromatography, the mobile phase composition was changed on five stationary phases including silica, diol, cyano, amino, and zwitterionic. Afterward, temperature, pH, and buffer concentration effects are studied. Results demonstrate a dual hydrophilic interaction liquid chromatography (HILIC)-reversed phase (RP) mechanism for the retention of NDELA. The transition between the HILIC and RP behavior on a different column, “U-turn” points, was observed between 43 and 68% of water in acetonitrile. The depiction of the natural logarithm of retention factor vs. inverse of the absolute temperature was linear for cyano, amino, and zwitterionic columns. In contrast, it was curvature for silica and diol columns. In each column, the positive slopes indicate a negative retention enthalpy, signifying an exothermic process of transferring analytes from the mobile phase to the stationary phases being examined. In the case of buffer pH and concentration, an ammonium acetate solution with a pH of 5.7 and a concentration of 10 mM was selected for further investigation. Finally, the selectivity of this method in optimal conditions for the analysis of NDELA in shampoo has been investigated. According to the well-obtained selectivity of NDELA in shampoo and the advantages of the HILIC method, this method seems to be a suitable alternative to RP methods.

A series of 2-[(2,6-diarylpiperidin-4-yl)hydrazono]-2,3-dihydrothiazoles (25–40) were synthesized by the reaction of respective thiosemicarbazones (9–24) with phenacyl bromide in the presence of sodium acetate-acetic acid buffer and refluxing in ethanol for 12–16 h. The newly synthesized target compounds were characterized by elemental analysis, mass, FT-IR, ¹H and ¹³C NMR spectroscopic methods. A Structure activity relationship study was carried out for the title compounds against a panel of bacterial strains viz Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, Bacillus subtilis and Klebsiella pneumonia and the fungal strains Cryptococcus neoformans, Candida albicans, Rhizopus sp, Aspergillus niger and Aspergillus flavus, respectively, using ciprofloxacin and amphotericin-B as standard drugs. These studies proved that compounds 26 and 34 against Staphylococcus aureus, 35 against P. aeruginosa, 38 against B. subtilis, and 27 against K. pneumonia showed maximum inhibitory potency at the lowest concentration (6.25 µg/mL), whereas 26, 34 and 35 against C. neoformans and 26 and 27 against Candida albicans showed beneficial antifungal activity at a minimum concentration (MIC) of 6.25 µg/mL.

A series of 1-(2-amino-2,4,5,6,7,7a-hexahydrobenzo[b]-3-yl)-3-substitued-phenylpropane-1,3-dionederivatives were synthesized using the Gewald synthesis in first step which is followed by Baker−Venkataraman rearrangement to yield title compounds. The FTIR, MS and 1H NMR results of the produced derivatives were validated. The biological potential such as antimicrobial, antioxidant and antimycobacterial activity against a particularly virulent strain of MTB (MTB H37Ra) of the synthesized compounds were examined. Antimicrobial screening outcomes showed that compound S₁₇ turned to be the most effective antibacterial agent against Gram positive bacteria such as Staphylococcus aureus (MIC = 16.87 µM) and Bacillus subtilis (MIC = 9.45 µM) and Gram negative bacteria such as Escherichia coli (MIC = 16.87 µM) and compound S₇ against Salmonella typhi (MIC = 9.74 µM) and compound S₁₆ displayed remarkable antifungal activity toward each Candida albicans and Aspergillus niger (MIC = 15.23 µM). The standard drugs, cefadroxil (antibacterial), have MIC value against S. aureus, B. subtilis, E. coli and S. Typhi are 16.40 µM, 32.80 µM, 16.40 µM and 16.40 µM, respectively, and fluconazole (antifungal) has MIC value 20.40 µM against both the C. albicans and A.niger strain. In comparison with ascorbic acid, a standard drug (IC₅₀ 44.91 µg/mL), compound S₁₀ demonstrated good antioxidant activity, with an IC₅₀ value of 45.29 µg/mL, according to the results of the antioxidant screening. The results of the in vitro antituberculosis screening showed that compound S₂₃ was found to be effective with an MIC value of 78.125 µg/mL. Molecular docking study of an enzymatic active site of “DprE1-decaprenylphosphoryl-β-D-ribose-2′-epimerase” shows a comparable binding mode to the native ligand with better docking score which contributes in understanding and development of models for ligand–protein interactions. Compound S₂₃ showed better docking score of − 8.516 as compared to the Isoniazid with the docking score of − 6.315 which in future will create the fundamental structural framework for MTB inhibition.

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