Design, synthesis and evaluate of imidazole, triazine and metastable oxazolone derivatives as chemosensor for detecting metals

Algohary, Ayman M.; Alhalafi, Mona H.

doi:10.1016/j.jscs.2022.101537

Cited by 3 publications

(5 citation statements)

References 37 publications

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“…From Figure S9b, PDA/PIDO possesses the highest HOMO energy and the lowest LUMO energy, indicative of its enhanced electron donating capability over the individual PDA and PIDO. Using the E LUMO and E HOMO of the existing compounds, we can calculate the reaction characteristics energy gap ( D E = E LUMO – E HOMO ). , As a result, the calculated energy gaps of PDA, PIDO, and PDA/PIDO are 1.06, 0.29, and 0.08 eV, respectively, revealing that PDA/PIDO has the strongest reactivity. These calculation results are consistent with the fact that PDA/PIDO delivers superior gold recovery capacity over the individual PDA and PIDO.…”

Section: Resultsmentioning

confidence: 99%

“…Meanwhile, the proportion of the carboxyl groups increases from 6.23 to 11.71%, suggesting the strong complexation of the amidoxime groups with Au(III). 53 To better understand the roles of PDA and PIDO in gold recovery, density functional theory (DFT) calculations are carried out. Based on the binding energies of AuCl 4 − with PDA, PIDO, and PDA/PIDO (Figure S9a), AuCl 4 − adsorptions by PDA, PIDO, and PDA/PIDO are spontaneous exothermic reactions, while PDA/PIDO has the strongest gold binding ability.…”

Section: Gold Recovery Mechanism On the Pda/pido Membranementioning

confidence: 99%

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Dual-Crosslinking Polydopamine/Poly(imide dioxime) Porous Network Membrane Enables Efficient and Selective Gold Recovery from e-Waste

Zhang,

Li,

Liu

et al. 2024

ACS EST Eng.

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With the sharp increase in electronic and electrical equipment as well as concomitant electronic waste, it is imperative to recover precious metals from secondary resources from the perspective of environment protection and sustainable development. Herein, a free-standing, dual-cross-linking polydopamine (PDA) in conjunction with poly(imide dioxime) (PIDO) porous membrane (denoted as PDA/PIDO) is fabricated via a facile interfacial polymerization method for gold recovery. As expected, the constructed PDA/PIDO membrane features a hierarchical porous structure, ample active sites, and excellent hydrophilicity, endowing it with an ultrahigh gold capture capacity (3368 mg g −1 ), fast equilibrium time (35 min), superior recovery selectivity (separation factor of Au/Cu = 5.4 × 10 5 , Au/Ni = 3.9 × 10 5 ), high flux (1050 L m 2 h −1 ), and high retention rate (98%). Furthermore, the proposed PDA/PIDO membrane is also competent for selective gold recovery from the central processing unit leachate with remarkable efficiency in a continuous-flowing filtration system, highlighting its huge potential in practical large-scale gold recovery from e-waste.

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Section: Resultsmentioning

confidence: 99%

Section: Gold Recovery Mechanism On the Pda/pido Membranementioning

confidence: 99%

Dual-Crosslinking Polydopamine/Poly(imide dioxime) Porous Network Membrane Enables Efficient and Selective Gold Recovery from e-Waste

Zhang,

Li,

Liu

et al. 2024

ACS EST Eng.

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“…These compounds, also known as azlactones, are classified as saturated or unsaturated, according to the type of exocyclic bond linked to the carbon from four position of this core [ 7 ]. Unsaturated oxazolones are important synthons for the synthesis of different compounds with vast biological potential, including amino acids, peptides, amides [ 8 , 9 , 10 , 11 , 12 ] and five- or six-membered heterocycles (imidazolones, tiazolones, triazinones, etc.) [ 7 , 8 , 9 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

“…Unsaturated oxazolones are important synthons for the synthesis of different compounds with vast biological potential, including amino acids, peptides, amides [ 8 , 9 , 10 , 11 , 12 ] and five- or six-membered heterocycles (imidazolones, tiazolones, triazinones, etc.) [ 7 , 8 , 9 , 12 ]. A great number of 4-aryliden-oxazol-5(4 H )-ones have a broad spectrum of biological activities that include antitumor [ 13 , 14 ], antibacterial [ 13 , 15 , 16 , 17 ], antifungal [ 13 , 15 , 16 , 17 ], anti-inflammatory [ 18 , 19 ], antioxidant [ 10 , 16 , 20 ] and antidiabetic [ 21 ] properties.…”

Section: Introductionmentioning

confidence: 99%

New Heterocyclic Compounds from Oxazol-5(4H)-one and 1,2,4-Triazin-6(5H)-one Classes: Synthesis, Characterization and Toxicity Evaluation

Barbuceanu,

Rosca,

Apostol

et al. 2023

Molecules

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This paper describes the synthesis of new heterocycles from oxazol-5(4H)-one and 1,2,4-triazin-6(5H)-one classes containing a phenyl-/4-bromophenylsulfonylphenyl moiety. The oxazol-5(4H)-ones were obtained via condensation of 2-(4-(4-X-phenylsulfonyl)benzamido)acetic acids with benzaldehyde/4-fluorobenzaldehyde in acetic anhydride and in the presence of sodium acetate. The reaction of oxazolones with phenylhydrazine, in acetic acid and sodium acetate, yielded the corresponding 1,2,4-triazin-6(5H)-ones. The structures of the compounds were confirmed using spectral (FT-IR, 1H-NMR, 13C-NMR, MS) and elemental analysis. The toxicity of the compounds was evaluated on Daphnia magna Straus crustaceans and on the budding yeast Saccharomyces cerevisiae. The results indicate that both the heterocyclic nucleus and halogen atoms significantly influenced the toxicity against D. magna, with the oxazolones being less toxic than triazinones. The halogen-free oxazolone had the lowest toxicity, and the fluorine-containing triazinone exhibited the highest toxicity. The compounds showed low toxicity against yeast cells, apparently due to the activity of plasma membrane multidrug transporters Pdr5 and Snq2. The predictive analyses indicated an antiproliferative effect as the most probable biological action. The PASS prediction and CHEMBL similarity studies show evidence that the compounds could inhibit certain relevant oncological protein kinases. These results correlated with toxicity assays suggest that halogen-free oxazolone could be a good candidate for future anticancer investigations.

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“…Due to their broad range of biological and pharmacological qualities, they have attracted much more attention [3]. They serve as intermediates and suitable building blocks for the production of a variety of physiologic active compounds like amino acids and heterocyclic compounds [4][5][6]. In addition, these compounds are particularly effective as antioxidants [7], antitumors [8], antimicrobials [9], and antihypertensives [10] agents.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis, Antibacterial and Antioxidant Evaluation of 2-Substituted-4-arylidene-5(4<i>H</i>)-oxazolone Derivatives

Saadi,

Adnan

2023

Indones. J. Chem.

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In this research, the synthesis of new substituted oxazolone derivatives is described via Erlenmeyer synthesis of N-acyl amino acid. Firstly, the azo derivative 1 was prepared by coupling the diazonium salt of 3-amino-4-methoxybenzoic acid with 4,5-dichloroimidazole in sodium hydroxide solution. Benzoyl chloride derivative 2, the key intermediate of the synthesis, was synthesized by the acylation of azo-carboxylic acid derivative 1 with thionyl chloride. The resulting acyl chloride derivative reacted with glycine in a basic catalyst to form a hippuric acid derivative 3. After that, oxazolone derivatives 4a–4f were prepared via the reaction of the hippuric acid derivative with various aromatic aldehydes. All new compound structures were confirmed by spectral techniques, i.e., FTIR, 1H-NMR, 13C-NMR spectroscopy, and elemental analysis. The antimicrobial activity (Staphylococcus aureus and Escherichia coli) of all new compounds was screened in vitro. The results against S. aureus and E. coli showed that most of the tested compounds have an activity ranging from moderate to low. The antioxidant activity of derivative 4a was also evaluated and showed good antioxidant activity.

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Design, synthesis and evaluate of imidazole, triazine and metastable oxazolone derivatives as chemosensor for detecting metals

Cited by 3 publications

References 37 publications

Dual-Crosslinking Polydopamine/Poly(imide dioxime) Porous Network Membrane Enables Efficient and Selective Gold Recovery from e-Waste

Dual-Crosslinking Polydopamine/Poly(imide dioxime) Porous Network Membrane Enables Efficient and Selective Gold Recovery from e-Waste

New Heterocyclic Compounds from Oxazol-5(4H)-one and 1,2,4-Triazin-6(5H)-one Classes: Synthesis, Characterization and Toxicity Evaluation

Synthesis, Antibacterial and Antioxidant Evaluation of 2-Substituted-4-arylidene-5(4<i>H</i>)-oxazolone Derivatives

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