A novel heterogeneous biocatalyst based on graphene oxide for synthesis of pyran derivatives
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ABSTRACT:
SUBMITTER: Amiri-Zirtol L
PROVIDER: S-EPMC10960842 | biostudies-literature | 2024 Jan
REPOSITORIES: biostudies-literature
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Project description:Nano graphene oxide/3-aminopyridine has been introduced as a new, efficient and robust heterogeneous organic catalyst for synthesis of spiro-indoline-pyranochromene derivatives. Nano graphene oxide/3-aminopyridine was provided in an easy and green way from GO. Firstly, graphene oxide (GO) was synthesized and then 3-aminopyridine was immobilized with covalent bonds on its surface as a nitrogenous organic compound, in this step we didn't use any organic or toxic substance. This bonding was easily performed due to the presence and reactivity of the epoxy groups in the GO structure. Because of its vast-surface nano-layers, GO could be effective in appropriate dispersion of 3-aminopyridine on its surface and increasing the catalyst performance. The new catalyst was analysed using different microscopic and spectroscopic techniques such as Fourier-transform infrared (FT-IR), field emission scanning electron microscope (SEM), energy-dispersive X-ray spectroscopy (EDS), X-ray diffraction (XRD) and thermogravimetric analysis (TGA). Our results showed that the distance between GO plates was increased in the presence of the modifying agent. This is due to the placement of the organic compound between the GO sheets. Finally, the ability of our new nano-catalyst in the synthesis of some spiro-indoline-pyranochromene and dihydropyranochromene derivatives was evaluated and acceptable results were obtained. Eight analogous of spiro-indoline-pyranochromene (4a-4 h) were synthesized in high yields and characterized. Using 3-aminopyridine as an organic and efficient catalyst, its stabilization by a simple method on GO, recycling of the catalyst up to 7 times and obtaining a highly pure product were the points that made the present work more attractive.
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Project description:Fur-imine-functionalized graphene oxide-immobilized copper oxide nanoparticles (Cu(II)-Fur-APTES/GO) are synthesized and found to be a cost-effective, efficient, and reusable heterogeneous nanocatalyst for the preparation of pharmaceutically important xanthene derivatives under greener solvent conditions. Cu(II)-Fur-APTES/GO exhibits excellent result in the synthesis of xanthenes with reduced reaction time (25-50 min) and higher yields (up to 95%) and has a simple procedure, ease of product separation, and no byproducts. Moreover, the nanocatalyst has a Cu loading of 13.5 at. % over functionalized GO which is far superior than the already known metal-based heterogeneous catalysts. The newly synthesized catalyst has been characterized by various physiochemical techniques such as X-ray photoelectron spectroscopy, X-ray diffraction, energy-dispersive X-ray, Raman spectroscopy for structural characterization, field emission scanning electron microscopy and high-resolution transmission electron microscopy for morphological characterization. The catalyst showed admirable recyclability up to five consecutive runs, and there was no appreciable loss in catalytic efficiency.
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Project description:Graphene oxide (GO) is an oxygenated functionalized form of graphene that has received considerable attention because of its unique physical and chemical properties that are suitable for a large number of industrial applications. Herein, GO is rapidly obtained directly from the oxidation of graphene using an environmentally friendly modified Hummers method. As the starting material consists of graphene flakes, intercalant agents are not needed and the oxidation reaction is enhanced, leading to orders of magnitude reduction in the reaction time compared to the conventional methods of graphite oxidation. With a superior surface area, the graphene flakes are quickly and more homogeneously oxidized since the flakes are exposed at the same extension to the chemical agents, excluding the necessity of sonication to separate the stacked layers of graphite. This strategy shows an alternative approach to quickly producing GO with different degrees of oxidation that can be potentially used in distinct areas ranging from biomedical to energy storage applications.
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Project description:As an important precursor and derivate of graphene, graphene oxide (GO) has received wide attention in recent years. However, the synthesis of GO in an economical and efficient way remains a great challenge. Here we reported an improved NaNO3-free Hummers method by partly replacing KMnO4 with K2FeO4 and controlling the amount of concentrated sulfuric acid. As compared to the existing NaNO3-free Hummers methods, this improved routine greatly reduces the reactant consumption while keeps a high yield. The obtained GO was characterized by various techniques, and its derived graphene aerogel was demonstrated as high-performance supercapacitor electrodes. This improved synthesis shows good prospects for scalable production and applications of GO and its derivatives.
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Project description:The catalytic activity of chitosan (Cs) and grafted Cs led to the preparation of terephthalohydrazide Cs Schiff's base hydrogel (TCsSB), which was then investigated as an eco-friendly biocatalyst for synthesizing novel thiazole derivatives. TCsSB exhibited greater surface area and higher thermal stability compared to Cs, making it a promising eco-friendly biocatalyst. We synthesized two novel series of thiazoles via the reaction of 2-(2-oxo-1,2-diphenylethylidene) hydrazine-1-carbothioamide with various hydrazonoyl chlorides and 2-bromo-1-arylethan-1-ones, employing ultrasonic irradiation and using TCsSB as a catalyst. A comparative study between Cs and TCsSB revealed higher yields than TCsSB. The methodology offered advantages such as mild reaction conditions, quick reaction times, and high yields. TCsSB could be reused multiple times without a significant loss of potency. The chemical structures of the newly synthesized compounds were verified through IR, 1H NMR, 13C NMR, and MS analyses. Six synthesized compounds were assessed for their in vitro antibacterial effectiveness by establishing the minimum inhibitory concentration against four distinct bacterial strains. The docking analyses revealed favorable binding scores against several amino acids within the selected protein (PDB Code-1MBT) for these compounds, with compound 4c exhibiting particularly noteworthy binding properties. Additionally, the in silico ADME parameter estimation for all compounds indicated favorable pharmacological properties for these compounds.
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Project description:This study aims to synthesize novel fused spiro-4H-pyran derivatives under green conditions to develop agents having antimicrobial activity. The synthesized compounds were initially screened for in vitro antibacterial activity against two Gram-positive and three Gram-negative bacterial strains, and all the compounds exhibited moderate to potent antibacterial activity. However, compound 4l showed significant inhibition toward all the bacterial strains, particularly against Streptococcus pneumoniae and Escherichia coli with minimum inhibitory concentration values of 125 μg/mL for each. The toxicity studies of selected compounds (4c, 4e, 4l, and 4m) using human red blood cells as well as human embryonic kidney (HEK-293) cells showed nontoxic behavior at desired concentration. Growth kinetic and time-kill curve studies of 4l against S. pneumoniae and E. coli supported its bactericidal nature. Interestingly, compound 4l showed a synergistic effect when used in combination with ciprofloxacin against selected strains. Biofilm formation in the presence of a lead compound, as assessed by XTT assay, showed complete disruption of the bacterial biofilm visualized by scanning electron microscopy. Overall, the findings suggest 4l to be considered as a promising lead for further development as an antibacterial agent.
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Project description:The synthesis of high quality graphene oxide (GO) in large quantities is a matter of great importance for both research institutes and industries. In the present study, we report an improvement in the so-called "improved method" reported by Tour et al., which had already improved the very famous "Hummers method" to a certain extent. Through an important pre-treatment step, GO with larger sheets, better structural integrity, and a higher yield of monolayers was obtained. Furthermore, both the oxidation time and temperature were reduced without reducing the degree of high oxidation. Even though a low temperature is known to be a prerequisite for obtaining less defective GO in its reduced form (rGO), we found through this research that the pre-treatment step minimizes the negative effect of the moderate temperature (35 °C) needed to enhance the reaction rate, without altering the basal graphitic plane, which was also preserved at a low temperature (<10 °C). Both the mechanical and electrical properties confirm the enhancement of the GO quality obtained through improving the improved method, and make the rGO films produced attractive for practical applications.
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