Synthesis and Antioxidant Properties of New Oxazole-5(4&lt;i&gt;H&lt;/i&gt;)-one Derivatives

Kuş, Canan; Uğurlu, Ezgi; Özdamar, Elçin Deniz; Can‐Eke, Benay

doi:10.4274/tjps.70299

Cited by 16 publications

(5 citation statements)

References 25 publications

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“…Derivatives (1a-c, 1e) and (1f) were prepared following our reported methods. 30,33 All known organic products (2d), 35 (9a-c), 38,39 and (11g) 37 were confirmed by comparison of their physical and spectral data with those of authentic samples. All of the melting points of the prepared compounds were determined on an Electrothermal IA9100 apparatus (UK).…”

Section: Methodsmentioning

confidence: 78%

An eco-compatible access to diversified bisoxazolone and bisimidazole derivatives

Arafa¹,

Abdel‐Magied²

2018

Arkivoc

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An efficient, straight-forward and eco-friendly synthetic strategy for the assembly of novel bisoxazolones via a four-component, sequential reaction of dialdehydes, glycine, benzoyl chloride and acetic anhydride, using ultrasound radiation, is described. Additionally, a diverse group of new bisimidazoles has been synthesized in good yields by the sonication of diamines and (Z)-4-arylidene-2-phenyloxazol-5(4H)-ones. These approaches have resulted in a number of successful routes for the facile synthesis of bis-oxazolone and bis-imidazole frameworks within minutes of irradiation. Excellent outcomes using these environmentally-friendly parameters make these synthetic schemes ideal, sustainable, green-chemistry procedures and provide simple access towards the preparation of bisheterocycles.

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Section: Methodsmentioning

confidence: 78%

An eco-compatible access to diversified bisoxazolone and bisimidazole derivatives

Arafa¹,

Abdel‐Magied²

2018

Arkivoc

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“…[ 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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“…Moreover, the oxazole nucleus and its derivatives are found in the structure of some medicinal compounds, such as: oxaprozin (anti-inflammatory), mubritinib (antitumoral), aleglitazar (antidiabetic), rilmenidine (antihypertensive), sulfamoxole (antibacterial) [5,15]. From oxazoles class, 2,4-disubstituted oxazole-5(4H)ones derivatives are standing out for their biological properties, including: antibacterial [3,[16][17][18][19], antifungal [3,17,19], antioxidant [17,20], anti-inflammatory [21] and antitumoral [22,23] activity. Regarding the antimicrobial activity, the in vitro study results performed on a series of (4Z)-4-(substituted benzylidene)-2-phenyl-oxazol-5(4H)-ones evaluated against some bacterial cultures (Pseudomonas aeruginosa, Staphylococcus Pyogenes, Klebsiella pneumonia, Methicillin resistant Staphylococcus aureus, Escherichia coli) and fungi (Candida albicans, Aspergillus fumigatus, Penicillium marneffei, Trichophyton mentagrophytes) demonstrated that the compounds have a significant biological activity, depending on the radicals grafted on the benzylidene fragment.…”

Section: Introductionmentioning

confidence: 99%

In Silico and Experimental Studies for the Development of Novel Oxazol-5(4h)-Ones With Pharmacological Potential

Roșca¹

2020

FARMACIA

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New 2-(4-(4-X-phenylsulfonyl)phenyl)-4-(3-bromo/3-bromo-4-methoxy-benzylidene)oxazol-5(4H)-ones have been synthesized by reaction of some 2-(4-(4-X-phenylsulfonyl)benzamido)acetic acids derivatives with 3-bromobenzaldehyde or 3-bromo-4methoxybenzaldehyde. The structures of the newly obtained heterocycles were elucidated by IR, 1 H-NMR, 13 C-NMR, mass spectra and elemental analysis. The cytotoxicity of the new oxazolones was evaluated using Artemia salina and Daphnia magna organisms and the in vitro antimicrobial activity was assessed on Gram-positive and Gram-negative bacterial and fungal strains. RezumatNoi 2-(4-(4-X-fenilsulfonil)fenil)-4-(3-bromo/3-bromo-4-metoxi-benziliden)-oxazol-5(4H)-one au fost sintetizate prin reacția unor derivați ai acidului 2-(4-(4-X-fenilsulfonil)benzamido)acetic cu 3-bromobenzaldehida sau 3-bromo-4-metoxibenzaldehida. Structurile noilor heterocicluri au fost elucidate prin spectrometrie în IR, 1 H-RMN, 13 C-RMN, spectre de masă și analiză elementală. Citotoxicitatea noilor oxazolone a fost evaluată pe modele experimentale animale reprezentate de Artemia salina and Daphnia magna. Compușii au fost testați in vitro pentru activitatea lor antimicrobiană față de tulpini bacteriene Gram-pozitive și Gramnegative și fungice.

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Synthesis and Antioxidant Properties of New Oxazole-5(4<i>H</i>)-one Derivatives

Cited by 16 publications

References 25 publications

An eco-compatible access to diversified bisoxazolone and bisimidazole derivatives

An eco-compatible access to diversified bisoxazolone and bisimidazole derivatives

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

In Silico and Experimental Studies for the Development of Novel Oxazol-5(4h)-Ones With Pharmacological Potential

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