Green Synthesis and Theoretical Study of New Azepinodiazepine Derivatives with Biological Activity: Application of Fe3O4/ZnO@MWCNT

被引:1
作者
Azizi, Zahra [1 ]
Ghazvini, Maryam [2 ]
Afrashteh, Siavash [3 ]
Hossaini, Zinatossadat [4 ]
机构
[1] Islamic Azad Univ, Dept Chem, Karaj Branch, Karaj, Iran
[2] Payame Noor Univ, Dept Chem, Tehran, Iran
[3] Islamic Azad Univ, Dept Text Engn, Qaemshahr Branch, Qaemshahr, Iran
[4] Islamic Azad Univ, Dept Chem, Qaemshahr Branch, Qaemshahr, Iran
关键词
Fe3O4; ZnO@MWCNTs MNCs; azepinodiazepine derivative; multicomponent reaction; alkyl bromide; isatin; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; FE3O4; NANOPARTICLES; PRACTICAL SYNTHESIS; EFFICIENT SYNTHESIS; CARBON NANOTUBES; ORGANIC-DYES; AB-INITIO; CATALYST; ANTIOXIDANT;
D O I
10.1080/10406638.2023.2217993
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this study, we synthesized azepinodiazepine derivatives in high yields using multicomponent reactions of isatins, activated acetylenic compounds, alkyl bromides, methyl aziridine and ammonium acetate in the presence of Fe3O4/ZnO@MWCNT as a high-performance catalyst and teiethyl amine in water at room temperature. The Fe3O4/ZnO@MWCNT synthesizes using Petasites hybridus rhizome water extract as a green media and moderate base. Also, the catalytic activity of the green synthesized Fe3O4/ZnO@MWCNT MNCs was evaluated in the reduction of organic pollutants such as 4-nitrophenol (4-NP) in water at mild conditions. The results indicated that the biosynthesized NCs have very high and effective catalytic activity for organic pollutants within a few seconds. Investigation of the antioxidant ability of synthesized compounds using radical trapping of diphenyl-picrylhydrazine (DPPH) and ferric reduction power experiment is another purpose of this research. Also, the antimicrobial activity of some synthesized compounds was proved by employing the disk diffusion test on Gram-positive and Gram-negative bacteria. Also, to better understanding reaction mechanism density functional theory (DFT) based quantum chemical methods have been applied. This procedure has some benefits such as short reaction time, products with excellent yields, simple catalyst and product separation.
引用
收藏
页码:2508 / 2534
页数:27
相关论文
共 124 条
[1]   PANI-Fe3O4@ZnO nanocomposite as magnetically recoverable organometallic nanocatalyst promoted synthesis of new Azo chromene dyes and evaluation of their antioxidant and antimicrobial activities [J].
Abdolmohammadi, Shahrzad ;
Hossaini, Zinatossadat ;
Poor Heravi, Mohammad Reza .
MOLECULAR DIVERSITY, 2022, 26 (04) :1983-1993
[2]   Ultrasound promoted and Kit-6 mesoporous silica-supported Fe3O4 magnetic nanoparticles catalyzed cyclocondensation reaction of 4-hydroxycoumarin, 3,4-methylenedioxyphenol, and aromatic aldehydes [J].
Abdolmohammadi, Shahrzad ;
Shariati, Shahab ;
Mirza, Behrooz .
APPLIED ORGANOMETALLIC CHEMISTRY, 2021, 35 (03)
[3]   Aqueous-Mediated green synthesis of novel spiro[indole-quinazoline] derivatives using kit-6 mesoporous silica coated Fe3O4 nanoparticles as catalyst [J].
Abdolmohammadi, Shahrzad ;
Shariati, Shahab ;
Fard, Narges Elmi ;
Samani, Amir .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (07) :2729-2737
[4]   TiO2 Nanoparticles Immobilized on Carbon Nanotubes: An Efficient Heterogeneous Catalyst in Cyclocondensation Reaction of Isatins with Malononitrile and 4-Hydroxycoumarin or 3,4-Methylenedioxyphenol under Mild Reaction Conditions [J].
Abdolmohammadi, Shahrzad ;
Rasouli Nasrabadi, Seyed Reza ;
Dabiri, Mohammad Reza ;
Banihashemi Jozdani, Sayed Mustafa .
APPLIED ORGANOMETALLIC CHEMISTRY, 2020, 34 (04)
[5]   Immobilized TiO2 nanoparticles on carbon nanotubes: an efficient heterogeneous catalyst for the synthesis of chromeno[b]pyridine derivatives under ultrasonic irradiation [J].
Abdolmohammadi, Shahrzad ;
Mirza, Behrooz ;
Vessally, Esmail .
RSC ADVANCES, 2019, 9 (71) :41868-41876
[6]   Fe3O4 MNPs as a green catalyst for syntheses of functionalized [1,3]-oxazole and 1H-pyrrolo-[1,3]-oxazole derivatives and evaluation of their antioxidant activity [J].
Abdolmohammadi, Shahrzad ;
Hossaini, Zinatossadat .
MOLECULAR DIVERSITY, 2019, 23 (04) :885-896
[7]   TiO2, NPs-Coated Carbone Nanotubes as a Green and Efficient Catalyst for the Synthesis of [1]Benzopyrano[b][1]benzopyranones and Xanthenols in Water [J].
Abdolmohammadi, Shahrzad .
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2018, 21 (08) :594-601
[8]   Five closely related 4-chloro-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepines: similar molecular structures but different supramolecular assemblies [J].
Acosta, Lina M. ;
Jurado, Jorge ;
Palma, Alirio ;
Cobo, Justo ;
Glidewell, Christopher .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2015, 71 :1062-+
[9]   Local application of SCH 39166 reversibly and dose-dependently decreases acetylcholine release in the rat striatum [J].
Acquas, E ;
Di Chiara, G .
EUROPEAN JOURNAL OF PHARMACOLOGY, 1999, 383 (03) :275-279
[10]   Antioxidant activity of Kelussia odoratissima Mozaff. in model and food systems [J].
Ahmadi, Fatemeh ;
Kadivar, Mahdi ;
Shahedi, Mohammad .
FOOD CHEMISTRY, 2007, 105 (01) :57-64