Green synthesis and antioxidant activity of novel series of benzofurans from euparin extracted of <i>Petasites hybridus</i>

Ezzatzadeh, Elham; Hossaini, Zinatossadat

doi:10.1080/14786419.2018.1428598

Cited by 38 publications

(18 citation statements)

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“…Herein, in continuation of my research and our studies for discovering new procedures for synthesis of important organic compounds, in this research a series of novel phosphonate derivatives containing quinazolinone were synthesized using an efficient one‐pot, five component reaction between 2,4‐dihydroxyacetophenone, 1 , isopropenylacetylene, 2 , 2‐amino‐ N ‐alkyl benzamide, 3 , dialkyl acetylenedicarboxylates, 4 , and trimethyl phosphite or triphenyl phosphite, 5 , in the presence of reusable 2D ZnO/Fe 3 O 4 nanocomposites in water at room temperature with very good yields (Scheme ). Furthermore, the antioxidant activities of the same synthesized derivatives, such as 6a , 6b , 6e and 6f , were investigated by DPPH (2, 2‐diphenyl‐1‐picrylhydrazyl) radical trapping and ferric ion decreasing power experiments.…”

Section: Introductionmentioning

confidence: 99%

2D ZnO/Fe₃O₄ nanocomposites as a novel catalyst‐promoted green synthesis of novel quinazoline phosphonate derivatives

Ezzatzadeh

Hossaini

2020

Applied Organom Chemis

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In this research a novel and efficient procedure for the preparation of phosphonate derivatives using the reaction of 2,4‐dihydroxyacetophenone, isopropenylacetylene, 2‐amino‐N‐alkyl benzamide, dialkyl acetylenedicarboxylates and trimethyl phosphite or triphenyl phosphite in the presence of reusable 2D ZnO/Fe3O4 nanocomposites in water at room temperature was investigated. The 2D ZnO/Fe3O4 nanocomposites were synthesized using ionic liquid [OMIM]Br as a stabilizer and soft template. In addition, the power of antioxidant for some prepared compounds was studied using trapping of radicals by DPPH and a ferric reduction activity potential experiment. As a result, compound 6f displayed a noteworthy power for trapping of free radicals and 6b exhibited excellent reducing power compared with standards (BHT and TBHQ). Moreover, the antimicrobial power of some prepared quinazolinone phosphonates was proved by employing the disk diffusion experiment on two kinds of bacteria, Gram‐positive and ‐negative bacteria. The obtained outcomes of disk diffusion test showed that these compounds prevented bacterial growth. Some advantages of this procedure are: short time of reaction, high yields of product and easy separation of catalyst and products.

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Section: Introductionmentioning

confidence: 99%

2D ZnO/Fe₃O₄ nanocomposites as a novel catalyst‐promoted green synthesis of novel quinazoline phosphonate derivatives

Ezzatzadeh

Hossaini

2020

Applied Organom Chemis

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“…[16] The wide variations of substituents in benzaldehyde (28) and 1,3-dione result in abundant dihydropyrimidine derivatives, and various acidic conditions are employed to catalyze the reaction. [17] For example, as shown as equation (6) in Figure 3, after the Biginelli reaction is accomplished among 6-methoxyltetralone (35) and 3,4,5-trimethoxylbenzaldehyde (36) in the presence of thiourea (29), the accessed dihydropyrimidine (37) carries out the condensation with 3-(2-oxo-2Hchromen-3-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde (38) and ClCH 2 COOH in the media of acetic anhydride. The large conjugation system in thiazolo [2,3-b]pyrimidinone (39) is beneficial for antibacterial efficacy because 39 provides with more substituents for docking with amino acids in E. coli.…”

Section: Biginelli Reactionmentioning

confidence: 99%

“…As a result, a furan moiety is appended to benzofuran scaffold in 91, which exhibits high ability to scavenge DPPH. [36] The Groebke 3CR becomes a promising protocol for constructing phenolic hydroxyl-free antioxidative skeletons. However, relative low antioxidative effects of imidazo [1,2-a] quinoxalines (81 and 84) imply that enlarging conjugation system of heterocycles might not be always beneficial for the amelioration of antioxidative effects.…”

Section: Groebke Reactionmentioning

confidence: 99%

“…As shown as equation (15) in Figure 6, the adjacent position of the −OH in euparin ( 88 ) performs an Aldol condensation with the aldehyde ( 28 ) to afford α,β‐unsaturated ketone ( 89 ), and 89 acts as the reagent (as 71 in equation (12) of Figure 5) to take part in the [4+1] cycloaddition with an isocyanide ( 90 ). As a result, a furan moiety is appended to benzofuran scaffold in 91 , which exhibits high ability to scavenge DPPH [36] . The Groebke 3CR becomes a promising protocol for constructing phenolic hydroxyl‐free antioxidative skeletons.…”

Section: Groebke Reactionmentioning

confidence: 99%

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Multicomponent Reactions for Integrating Multiple Functional Groups into an Antioxidant

Liu

2020

The Chemical Record

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A large number of convincing evidences has revealed the correlation of the pathogeny of diseases with the oxidative damages of DNA, protein, biomembrane, and other biological species, while supplementation of antioxidants is demonstrated to be a promising way to avoid, at least, rectify the unbalance redox status in vivo. Although many endeavors have focused on synthesis of antioxidants, a main hurdle still hinders the wide usages of synthetic antioxidants because of low bioavailability and potential cytotoxicity. The search for antioxidants with multiple functional groups being recognized by different receptors becomes a much sought by researchers, and multicomponent reactions (MCRs) provide with powerful tools for the construction of multifunctional antioxidants. Presented herein is a personal account on the application of MCRs for the synthesis of multifunctional antioxidants, while radical-induced oxidation of DNA acts as the experimental system for evaluating antioxidative effect. Concretely, the Biginelli three-component reaction (3CR) affords such a dihydropyrimidine scaffold that the tautomerization between C=S and CÀ SH leads to antioxidative effect. The Povarov 3CR is able to integrate multiple antioxidative groups, i. e., ferrocenyl and À N(CH 3) 2 , into a quinoline scaffold, while the Groebke 3CR provides with imidazo[1,2-a]pyridine skeleton for inhibiting DNA oxidation. Additionally, the Knoevenagel-related MCRs also become efficient strategies for achieving radical-scavengers. On the other hand, the Ugi 4CR and Passerini 3CR result in the dipeptide and α-acyloxycarboxamide, respectively, with the benefit for the integration of antioxidative features by aliphatic chains. Therefore, MCRs have emerged as efficient tools for integrating multiple antioxidative features into one molecule in order to meet with complicated requirements from various biological surroundings.

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“…For this reason, discovering suitable and new methods to reduce these pathogens is significant, and recent investigation has focused on the evaluation of antibacterial effects on the synthesized compounds. Herein, in continuing research of my study for finding out new process for generation of valuable organic compounds, [42][43][44][45][46][47][48][49][50][51][52] herein, we considered a green process for the generation of some naphthyridine derivatives 7 via a multicomponent reactions of phthalaldehyde 1, 2-aminoacetonitrile 2, activated acetylenic compounds 3, alkyl bromides 4, triphenylphosphine 5 and ammonium acetate 6 in the presence of a catalytic amount of ZnO/Ag/Fe 3 O 4 /CNTs NPs in water at room temperature with excellent yields (Scheme 1).…”

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confidence: 99%

ZnO/Ag/Fe₃O₄ nanoparticles supported on carbon nanotubes employing Petasites hybridus rhizome water extract: A novel organometallic nanocatalyst for the synthesis of new naphthyridines

Hossaini

Tabarsaei

Khandan

et al. 2021

Applied Organom Chemis

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In this study, ZnO/Ag/Fe 3 O 4 /CNTs nanoparticles (NPs) immobilized on carbon nanotubes (ZnO/Ag/Fe 3 O 4 /CNTs) were synthesized using Petasites hybridus rhizome water extract as a renewable, mild, and safe reducing agent and effective stabilizer without adding any surfactants. For the confirmation of the structure of the green synthesized NPs, various methods such as X-ray diffraction (XRD), FESEM, transmission electron microscopy (TEM), Energy-Dispersive X-Ray Spectroscopy (EDS), and Vibrating Sample Magnetometer (VSM) were employed. The ZnO/Ag/Fe 3 O 4 /CNTs magnetic NPs as a high performance catalyst was employed for the preparation of naphthyridine derivatives in high yields via the multicomponent reactions of phthalaldehyde, 2-aminoactonitrile, activated acetylenic compounds, α-haloketones, triphenyphophine, and ammonium acetate in aqueous media at ambient temperature. Due to having isoquinoline core, we investigate antioxidant property of some synthesized compounds by diphenylpicrylhydrazine (DPPH) radical trapping and power of ferric reduction experiment. Furthermore, the disk diffusion test on Gram-positive and Gram-negative bacteria IS utilized for investigation of antimicrobial activity of some naphthyridines. The achieved outcomes of this experiment demonstrate that these synthesized compounds could prevent from growth of bacteria. Short time of reaction, high yields of product, easy separation of catalyst, and products are some benefits of this process. K E Y W O R D S alkyl bromide, multicomponent reaction, naphthyridine derivatives, ZnO/Ag/Fe 3 O 4 /CNTs nanoparticles 1 | INTRODUCTION The naphthyridine derivatives are significant heterocyclic compounds due to their broad spectrum of biological activities such as antihypertensives, antiarrhythmics, herbicide safeners, and immunostimulants. [1-3] The compounds containing a naphthyridine scaffold are a small class of bispyridine structures identified in various living organisms (plants, sponges, tunicates, and bryozoans). These natural products usually possess variant biological

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Green synthesis and antioxidant activity of novel series of benzofurans from euparin extracted of Petasites hybridus

Cited by 38 publications

References 43 publications

2D ZnO/Fe₃O₄ nanocomposites as a novel catalyst‐promoted green synthesis of novel quinazoline phosphonate derivatives

2D ZnO/Fe₃O₄ nanocomposites as a novel catalyst‐promoted green synthesis of novel quinazoline phosphonate derivatives

Multicomponent Reactions for Integrating Multiple Functional Groups into an Antioxidant

ZnO/Ag/Fe₃O₄ nanoparticles supported on carbon nanotubes employing Petasites hybridus rhizome water extract: A novel organometallic nanocatalyst for the synthesis of new naphthyridines

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Green synthesis and antioxidant activity of novel series of benzofurans from euparin extracted of Petasites hybridus

Cited by 38 publications

References 43 publications

2D ZnO/Fe3O4 nanocomposites as a novel catalyst‐promoted green synthesis of novel quinazoline phosphonate derivatives

2D ZnO/Fe3O4 nanocomposites as a novel catalyst‐promoted green synthesis of novel quinazoline phosphonate derivatives

Multicomponent Reactions for Integrating Multiple Functional Groups into an Antioxidant

ZnO/Ag/Fe3O4 nanoparticles supported on carbon nanotubes employing Petasites hybridus rhizome water extract: A novel organometallic nanocatalyst for the synthesis of new naphthyridines

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2D ZnO/Fe₃O₄ nanocomposites as a novel catalyst‐promoted green synthesis of novel quinazoline phosphonate derivatives

2D ZnO/Fe₃O₄ nanocomposites as a novel catalyst‐promoted green synthesis of novel quinazoline phosphonate derivatives

ZnO/Ag/Fe₃O₄ nanoparticles supported on carbon nanotubes employing Petasites hybridus rhizome water extract: A novel organometallic nanocatalyst for the synthesis of new naphthyridines