Synthesis and investigation of antioxidant and antimicrobial activity of new pyrazinopyrroloazepine derivatives using Fe3O4/CuO/ZnO@MWCNT MNCs as organometallic nanocatalyst by new MCRs

被引:5
作者
Amiri, Somayeh Soleimani [1 ]
Hossaini, Zinatossadat [2 ]
Azizi, Zahra [1 ]
机构
[1] Islamic Azad Univ, Dept Chem, Karaj Branch, Karaj, Iran
[2] Islamic Azad Univ, Dept Chem, Qaemshahr Branch, Qaemshahr, Iran
关键词
alkyl bromide; Fe3O4; CuO; ZnO@MWCNT MNCs; five component reaction; isatoic anhydride; pyrazinopyrroloazepine derivatives; PROMOTED EFFICIENT SYNTHESIS; SOLVENT-FREE SYNTHESIS; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; GREEN SYNTHESIS; RING-EXPANSION; ACTIVATED ACETYLENES; PRIMARY AMINES; AERIAL PART; 3-COMPONENT;
D O I
10.1002/aoc.6573
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In this study, we synthesized pyrazinopyrroloazepine derivatives in high yields using multicomponent reactions of isatoic anhydride, N-methylimidazole, alkyl bromides, activated acetylenic compounds, ethyl glycinate and methyl aziridine in the presence of Fe3O4/CuO/ZnO@MWCNT as a high performance catalyst in water at room temperature. The Fe3O4/CuO/ZnO@MWCNT synthesizes using Petasites hybridus rhizome water extract as a green media and moderate base. As well Fe3O4/CuO/ZnO@MWCNT MNCs show a good improvement in the yield of the product and displayed significant reusable activity. Investigation of antioxidant ability of synthesized compounds using radical trapping of diphenyl-picrylhydrazine (DPPH) and ferric reduction power experiment is another purpose in this research. Because of having two NH groups in the synthesized compounds, these compounds shown the good antioxidant activity relative two standards. Compound 7c was shown excellent antioxidant activity. Also, the antimicrobial activity of some synthesized compounds proved by employing the disk diffusion test on gram-positive and gram-negative bacteria. The pyrazinopyrroloazepines 7a, 7c, 7d and 7f have the maximum effect on Escherichia coli compared with gram-positive and gram-negative bacteria because of good inhibition zone diameter. This procedure has some benefits such as short reaction time, product with excellent yields, simple catalyst and products separation.
引用
收藏
页数:15
相关论文
共 50 条
  • [41] Highly Efficient Ag/Fe3O4@MWCNTs MNCs Catalyzed Green Synthesis of New Derivatives of 1,2,4-Triazine: The Cytotoxic Activity Investigation of 1,2,4-Triazines
    Iravani, Nasir
    Barani, Khatereh Khandan
    Moradian, Majid
    Hossaini, Zinatossadat
    APPLIED ORGANOMETALLIC CHEMISTRY, 2025, 39 (03)
  • [42] Green Synthesis of New Coumarins Employing SiO2/Fe3O4@MWCNTs as a Recyclable Catalyst and Evaluation of Antioxidant and Antiproliferative Activity
    Hojjati, Mahsa
    Shikholeslami-Farahani, Fatemeh
    Shahvelayati, Ashraf Sadat
    Hossaini, Zinatossadat
    APPLIED ORGANOMETALLIC CHEMISTRY, 2025, 39 (03)
  • [43] Green Synthesis of New Pyrimidine Fused Quinolines Derivatives and Reduction of Organic Pollutants Using Fe3O4/KF/Clinoptilolite Supported on MWCNTs
    Ezzatzadeh, Elham
    Hossaini, Zinatossadat
    Majedi, Soma
    Hussain, Faiq H. S.
    POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (05) : 4707 - 4728
  • [44] Synthesis of benzo[b]pyran and pyrano[2,3-d]pyrimidine derivatives using a new superparamagnetic nanocatalyst Fe3O4@gly@Furfural@Co(NO3)2
    Keshani, Raheleh
    Hazeri, Nourallah
    Faroughi Niya, Homayoun
    Fatahpour, Maryam
    RESEARCH ON CHEMICAL INTERMEDIATES, 2023, 49 (08) : 3461 - 3479
  • [45] Immobilized Cu(II) Schiff base complex supported on Fe3O4 magnetic nanoparticles: A highly efficient and reusable new catalyst for the synthesis of pyranopyridine derivatives
    Azarifar, Davood
    Mahmoudi-GomYek, Samaneh
    Ghaemi, Masoumeh
    APPLIED ORGANOMETALLIC CHEMISTRY, 2018, 32 (12)
  • [46] A new combustion method for the synthesis of copper oxide nano sheet and Fe3O4/CuO magnetic nanocomposite and its application in removal of diazinon pesticide
    Yeganeh-Faal, Ali
    Kadkhodaei, Maryam
    RESULTS IN ENGINEERING, 2022, 16
  • [47] Synthesis of novel pyrano[2,3-f]chromene-dione derivatives using phosphoric acid-functionalized silica-coated Fe3O4 nanoparticles as a new reusable solid acid nanocatalyst
    Sedighimehr, Iman
    Karami, Bahador
    Farahi, Mahnaz
    Keshavarz, Mosadegh
    MOLECULAR DIVERSITY, 2022, 26 (06) : 3325 - 3336
  • [48] Ionic liquid as an effective green media for the synthesis of (5Z, 8Z)-7H-pyrido[2,3-d]azepine derivatives and recycable Fe3O4/TiO2/multi-wall cabon nanotubes magnetic nanocomposites as high performance organometallic nanocatalyst
    Kohestani, Tayyebeh
    Sayyed-Alangi, S. Zahra
    Hossaini, Zinatossadat
    Baei, Mohammad T.
    MOLECULAR DIVERSITY, 2022, 26 (03) : 1441 - 1454
  • [49] Synthesis and Antimicrobial Activity of Chalcone-Derived 1,4-Dihydropyridine Derivatives Using Magnetic Fe2O3@SiO2 as Highly Efficient Nanocatalyst
    Malhi, Dharambeer Singh
    Kaur, Navneet
    Kaur, Manvinder
    Han, Haesook
    Bhowmik, Pradip K.
    Husain, Fohad Mabood
    Sohal, Harvinder Singh
    Verma, Meenakshi
    CATALYSTS, 2025, 15 (03)
  • [50] Bio-Fe3O4-MNPs catalyzed green synthesis of pyrrolo[2,1-a]isoquinoline derivatives using isoquinolium bromide salts: study of antioxidant activity
    Abbasi, Maryam
    Hargalani, Fariba Zamani
    Afrashteh, Siavash
    Rostamian, Rezvaneh
    CANADIAN JOURNAL OF CHEMISTRY, 2019, 97 (12) : 848 - 855