Synthesis of different α, β- unsaturated oxazolone derivatives

Phalke, Pallavi L

doi:10.22270/jddt.v9i1.2189

Cited by 5 publications

(5 citation statements)

References 8 publications

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“…Yasaei et al [40] synthesize oxazole derivatives by heating trifluoroacetic acid-ketoneamides with acid labile substituted alkoxy molecules which undergo formation of a 5-acetyl-substituted oxazole derivative. Phalke [41] added acetyl glycine, various aldehydes, anhydrous sodium acetate and acetic anhydride to the flask. Continuously stir with warming until the completion of the reaction.…”

Section: Modern Synthetic Methods For Oxazolesmentioning

confidence: 99%

Recent Development and Green Approaches for Synthesis of Oxazole Derivatives: A Review

Joshi¹,

Choudhary²

2022

IJPS

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Green Synthetic Methods Synthesis of Oxazole DerivativesThis review compiles green synthetic methods intended for the synthesis of oxazole derivatives. Oxazoles are a class of compounds with a wide range of biological activities. The application and biological activity of oxazoles is highly dependent on their structure. Now-a-days, scientists have been performing the synthesis of oxazole derivatives. High demands in synthesis often result in the production of various hazardous chemical substances. So, to minimize the production of toxic chemical substances, green synthetic approaches are used in this manner. Green synthesis covers different synthetic approaches, including the application of microwave techniques, ultrasound, ionic liquids, deep-eutectic solvents, the use of catalysts and continuous flow synthesis. In this review, the authors mentioned that not only these green synthetic approaches reduce the formation and utilisation of toxic chemicals, but there is an increase in the reaction performance that enhances the product yields, purity, post-synthetic processes and energy consumption when compared to conventional methods. Due to the biological and pharmacological significance of oxazoles and the demands of decreasing toxic solvents, catalysts, and energy consumption, this article gives a full literature survey on the significance of green synthetic methods in oxazole synthesis. It contains a literature survey over the period from 2010-2020. The emphasis of this article is its comprehensive literature survey on oxazole, which is helpful for the researchers working on the oxazole scaffold and gaining information on the green synthetic approaches to their synthesis.

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Section: Modern Synthetic Methods For Oxazolesmentioning

confidence: 99%

Recent Development and Green Approaches for Synthesis of Oxazole Derivatives: A Review

Joshi¹,

Choudhary²

2022

IJPS

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“…Antioxidant property concerns with hydroxyl group in aromatic ring. The hydroxyl group gives the hydrogen atom to neutralize the free radical present in the body and shows the potent effect of drug 5,7 . Thus, the present study was designed to evaluate the antioxidant activity of oxazole derivatives by hydrogen peroxide method.…”

Section: Quick Response Codementioning

confidence: 99%

Untitled

2023

IJPSR

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The present study is reported the antioxidant activity of oxazole derivatives. Oxazole are five-member heterocyclic ring containing nitrogen and oxygen as a hetero atom. Due to binding with a wide spectrum of receptors and enzymes easily in biological systems through various non-covalent interactions, oxazole-based molecules are becoming a kind of significant heterocyclic nucleus, which have received attention from researchers globally, leading them to synthesize diverse oxazole derivatives. Oxazole have been reported to possess diverse biological activities like antimicrobial, antiviral, anti-inflammatory and anticancer activity. In this research work some heterocyclic like 4-(substituted benzylidene)-2-(pyrazin-2-yl) oxazol-5(4H)-one with potent derivatives for 100 ug/ml are 4-( 4-methylbenzylidene)-2-(pyrazin-2-yl) oxazol-5(4H)-one (PA-7), 4-(3-bromo-4-hydroxy-5 methoxybenzylidene) -2-(pyrazin-2-yl)oxazol-5(4H)one (PA-13) and are 4-(5-Oxo)-2-(pyrazin-2-yl) 4(5H)-ylidene) methyl) benzonitrile (PA-15) and for 200 ug/ml 4-(4-fluoro benzylidene)-2-(pyrazin-2yl) oxazol-5(4H)-one (PA-4), 4-(4-hydroxy-3-methoxy benzylidene)-2-(pyrazin-2-yl) oxazol-5 (4H)-one (PA-8) and 4-(3-bromo-4-hydroxy-5 methoxybenzylidene) -2-(pyrazin-2-yl) oxazol-5(4H)-one (PA-13) shows promising anti-oxidant activities. The method mainly used as hydrogen peroxide radical scavenging activity. Antioxidant scavenging effect of synthesized derivatives also compared with standard Ascorbic acid.

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“…5,6-Diaminouracils 1a-e, the key starting material for the obtained compounds, were synthesized by the reaction between ethyl cyanoacetate and different urea derivatives followed by nitrosation and reduction by conventional methods [25,38,39]. The Erlenmeyer azlactones (2a-c), also known as 4-arylideno-5(4H)-1,3-oxazolones, were synthesized according to literature [40][41][42][43] through an aldol-type condensation of a glycine-based azlactone (A) with different aldehydes (Scheme 2). The mechanistic pathway for the formation of azlactones 2a-c was explained in (Scheme 3).…”

Section: Chemistrymentioning

confidence: 99%

“…These compounds were prepared according to a reported method [25,38,39]. 4-arylideno-5(4H)-1,3-oxazolones (2a-c) These compounds were prepared according to a reported method [40][41][42][43].…”

Section: Materials and Instrumentsmentioning

confidence: 99%

Synthesis, In Silico Prediction and In Vitro Evaluation of Antimicrobial Activity, DFT Calculation and Theoretical Investigation of Novel Xanthines and Uracil Containing Imidazolone Derivatives

El‐Kalyoubi

Agili

Zordok

et al. 2021

IJMS

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Novel xanthine and imidazolone derivatives were synthesized based on oxazolone derivatives 2a-c as a key intermediate. The corresponding xanthine 3-5 and imidazolone derivatives 6-13 were obtained via reaction of oxazolone derivative 2a-c with 5,6-diaminouracils 1a-e under various conditions. Xanthine compounds 3-5 were obtained by cyclocondensation of 5,6-diaminouracils 1a-c with different oxazolones in glacial acetic acid. Moreover, 5, 6-diaminouracils 1a-e were reacted with oxazolones 2a-c in presence of drops of acetic acid under fused condition yielding the imidazolone derivatives 6-13. Furthermore, Schiff base of compounds 14-16 were obtained by condensing 5, 6-diaminouracils 1a,b,e with 4-dimethylaminobenzaldehyde in acetic acid. The structural identity of the resulting compounds was resolved by IR, 1H-, 13C-NMR and Mass spectral analyses. The novel synthesized compounds were screened for their antifungal and antibacterial activities. Compounds 3, 6, 13 and 16 displayed the highest activity against Escherichia coli as revealed from the IC50 values (1.8–1.9 µg/mL). The compound 16 displayed a significant antifungal activity against Candia albicans (0.82 µg/mL), Aspergillus flavus (1.2 µg/mL) comparing to authentic antibiotics. From the TEM microgram, the compounds 3, 12, 13 and 16 exhibited a strong deformation to the cellular entities, by interfering with the cell membrane components, causing cytosol leakage, cellular shrinkage and irregularity to the cell shape. In addition, docking study for the most promising antimicrobial tested compounds depicted high binding affinity against acyl carrier protein domain from a fungal type I polyketide synthase (ACP), and Baumannii penicillin- binding protein (PBP). Moreover, compound 12 showed high drug- likeness, and excellent pharmacokinetics, which needs to be in focus for further antimicrobial drug development. The most promising antimicrobial compounds underwent theoretical investigation using DFT calculation.

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Synthesis of different α, β- unsaturated oxazolone derivatives

Cited by 5 publications

References 8 publications

Recent Development and Green Approaches for Synthesis of Oxazole Derivatives: A Review

Recent Development and Green Approaches for Synthesis of Oxazole Derivatives: A Review

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Synthesis, In Silico Prediction and In Vitro Evaluation of Antimicrobial Activity, DFT Calculation and Theoretical Investigation of Novel Xanthines and Uracil Containing Imidazolone Derivatives

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