Highly facilitated synthesis of phenyl(tetramethyl)acridinedione pharmaceuticals by a magnetized nanoscale catalytic system, constructed of GO, Fe3O4 and creatine

被引:31
作者
Eyvazzadeh-Keihan, Reza [1 ]
Bahrami, Negar [1 ]
Taheri-Ledari, Reza [1 ]
Maleki, Ali [1 ]
机构
[1] Iran Univ Sci & Technol, Dept Chem, Catalysts & Organ Synth Res Lab, Tehran 1684613114, Iran
基金
美国国家科学基金会;
关键词
Catalysis; Graphene oxide; Magnetite; Materials engineering; Organic synthesis; REDUCED GRAPHENE OXIDE; ONE-POT SYNTHESIS; HETEROGENEOUS CATALYST; EFFICIENT SYNTHESIS; MULTICOMPONENT SYNTHESIS; ORGANIC-SYNTHESIS; IONIC LIQUIDS; NANOPARTICLES; GREEN; ACID;
D O I
10.1016/j.diamond.2019.107661
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
Here, an efficient heterogeneous catalytic system, made of graphene oxide (GO) nano-sheets, iron oxide nano-particles (Fe3O4 NPs), and creatine (CR), is presented. Firstly, this novel designed catalytic system (GO/CR-Fe3O4) has been fabricated via a convenience method and magnetized via an in situ process. Then, it has been suitably applied for catalyzing the synthesis of 9-phenyl-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-acridine-1,8(2H,5H)-dione (PTAD) derivatives, as one of the most important family of pharmaceutical compounds. As the first and foremost advantage of this catalytic system, this can be referred that the GO/CR-Fe3O4 NPs are magnetically separated from the reaction mixture through their high paramagnetic behavior. In fact, the Fe3O4 NPs that are responsible for the magnetic property, are well intercalated between the GO's nano-sheets during the fabrication process. Electron microscopy (EM) has clearly disclosed this effective structure of the produced nanocomposite. Then, the substantial catalytic performance of this system for facilitating the PTAD synthesis is shown. In this work, this is exhibited that high reaction yields (98%) are obtained during short reaction times (10 min), through using a partial amount of nanocatalyst (0.03 g). Additionally, the catalysis reusability is also investigated after a five-time running the catalytic process.
引用
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页数:8
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共 49 条
  • [1] Novel acridinedione derivatives: Design, synthesis, SIRT1 enzyme and tumor cell growth inhibition studies
    Alvala, Mallika
    Bhatnagar, Shubhmita
    Ravi, Alvala
    Jeankumar, Variam Ullas
    Manjashetty, Thimmappa H.
    Yogeeswari, Perumal
    Sriram, Dharmarajan
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (09) : 3256 - 3260
  • [2] SnCl4-functionalized nano-Fe3O4 encapsulated-silica particles as a novel heterogeneous solid acid for the synthesis of 1,4-dihydropyridine derivatives
    Bamoniri, Abdolhamid
    Fouladgar, Sara
    [J]. RSC ADVANCES, 2015, 5 (96) : 78483 - 78490
  • [3] A new approach to polymer-supported phosphotungstic acid: Application for glycerol acetylation using robust sustainable acidic heterogeneous-homogenous catalyst
    Betiha, M. A.
    Hassan, Hassan M. A.
    El-Sharkawy, E. A.
    Al-Sabagh, A. M.
    Menoufy, M. F.
    Abdelmoniem, H-E. M.
    [J]. APPLIED CATALYSIS B-ENVIRONMENTAL, 2016, 182 : 15 - 25
  • [4] A rapid and green method for expedient multicomponent synthesis of N-substituted decahydroacridine-1,8-diones as potential antimicrobial agents
    Bhosle, Manisha R.
    Nipte, Dhananjay
    Gaikwad, Jivan
    Shaikh, Moseen A.
    Bondle, Giribala M.
    Sangshetti, Jaiprakash N.
    [J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (11) : 7047 - 7064
  • [5] Organic synthesis provides opportunities to transform drug discovery
    Blakemore, David C.
    Castro, Luis
    Churcher, Ian
    Rees, David C.
    Thomas, Andrew W.
    Wilson, David M.
    Wood, Anthony
    [J]. NATURE CHEMISTRY, 2018, 10 (04) : 383 - 394
  • [6] N-Propyl benzoguanamine sulfonic acid supported on magnetic Fe3O4 nanoparticles: a novel and efficient magnetically heterogeneous catalyst for the synthesis of 1,8-dioxo-decahydroacridine derivatives
    Dehbalaei, Masoumeh Gholami
    Foroughifar, Naser
    Pasdar, Hoda
    Khajeh-Amiri, Alireza
    [J]. NEW JOURNAL OF CHEMISTRY, 2018, 42 (01) : 327 - 335
  • [7] Nanocrystalline TiO2, via green combustion synthesis, as an efficient and reusable catalyst for the preparation of 1,8-dioxooctahydroxanthenes and 1,8-dioxodecahydroacridines
    Eidi, Esmaiel
    Kassaee, Mohammad Zaman
    Nasresfahani, Zahra
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2015, 29 (12) : 793 - 797
  • [8] Recent advances in the application of mesoporous silica-based nanomaterials for bone tissue engineering
    Eivazzadeh-Keihan, Reza
    Chenab, Karim Khanmohammadi
    Taheri-Ledari, Reza
    Mosafer, Jafar
    Hashemi, Seyed Masoud
    Mokhtarzadeh, Ahad
    Maleki, Ali
    Hamblin, Michael R.
    [J]. MATERIALS SCIENCE AND ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS, 2020, 107
  • [9] Carbon based nanomaterials for tissue engineering of bone: Building new bone on small black scaffolds: A review
    Eivazzadeh-Keihan, Reza
    Maleki, Ali
    de la Guardia, Miguel
    Bani, Milad Salimi
    Chenab, Karim Khanmohammadi
    Pashazadeh-Panahi, Paria
    Baradaran, Behzad
    Mokhtarzadeh, Ahad
    Hamblin, Michael R.
    [J]. JOURNAL OF ADVANCED RESEARCH, 2019, 18 : 185 - 201
  • [10] Synthesis and Evaluation of Poly(Sodium 2-Acrylamido-2-Methylpropane Sulfonate-co-Styrene)/Magnetite Nanoparticle Composites as Corrosion Inhibitors for Steel
    El-Mahdy, Gamal A.
    Atta, Ayman M.
    Al-Lohedan, Hamad A.
    [J]. MOLECULES, 2014, 19 (02) : 1713 - 1731