Ultrasound-Assisted Synthesis of Nitrogen and Oxygen Containing Heterocycles Using Fluorinated Graphene Oxide as Catalyst: Evaluation of Their Anthelmintic Activities

被引:5
|
作者
Dutta, Arup [1 ]
Chhetri, Bhusan [3 ]
Nongrum, Ridaphun [2 ]
Kupar Kharmawlong, George [1 ]
Yadav, Arun K. [3 ]
Nongkhlaw, Rishanlang [1 ]
机构
[1] North Eastern Hill Univ, Dept Chem, Shillong 793022, Meghalaya, India
[2] Sankardev Coll, Dept Chem, Shillong 793004, Meghalaya, India
[3] North Eastern Hill Univ, Dept Zool, Shillong 793022, Meghalaya, India
来源
CHEMISTRYSELECT | 2020年 / 5卷 / 25期
关键词
Anthelmintic Activities; Fluorinated Graphene Oxide Heterocylces; Molecular docking; Spirooxindole; BOND-FORMING REACTIONS; SPIROOXINDOLE DERIVATIVES; METAL; OXINDOLES; ACID;
D O I
10.1002/slct.202001442
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Spirooxindole derivatives have been efficiently synthesizedviaa three-component reaction consisting of isatin, malononitrile/ pyrazole and various 1,3-diketones using Fluorinated Graphene Oxide (FGO) as a green and metal free carbocatalyst, under sonication. The main advantages of this synthetic approach lie in its operational simplicity, easy catalyst recovery and recyclability, high yields and short reaction times. The prepared catalyst was characterized by various analytical techniquesviz.,UV-Vis,FT-IRSpectroscopy,TGA,TEM,FE-SEMandEDX. The in vitro anthelmintic screening of synthesized compounds against a cestode,Raillietinasp. and a nematode parasite,Syphacia obvelataat 200 mu g/mL and 800 mu g/mL were also carried out which revealed a profound activity, with much reduced morality time of parasite. The SEM study indicated structure alterations in treated parasite, further validating the in vitro anthelmintic property. In addition, molecular docking studies were carried out against beta-tubulin protein to determine binding affinity of the synthesized compounds. All test compound followed the "Lipinski Rule of Five" and in silico pharmacokinetic investigation showed inhibitory activity against CYP enzyme and P-glycoprotein which may further improve the bio efficacy of compounds.
引用
收藏
页码:7474 / 7481
页数:8
相关论文
共 50 条
  • [1] Ultrasound-assisted Synthesis of Nitrogen and Oxygen Containing Heterocycles
    Wahan, Simranpreet K.
    Bhargava, Gaurav
    Chawla, Pooja A.
    CURRENT ORGANIC CHEMISTRY, 2023, 27 (12) : 1010 - 1019
  • [2] Ultrasound-Assisted Nitrogen and Boron Codoping of Graphene Oxide for Efficient Oxygen Reduction Reaction
    Zhang, Mingli
    Tao, Hengcong
    Liu, Yongchao
    Yan, Chao
    Hong, Song
    Masa, Justus
    Robertson, Alex W.
    Liu, Shizhen
    Qiu, Jieshan
    Sun, Zhenyu
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (03) : 3434 - 3442
  • [3] Recent developments using malononitrile in ultrasound-assisted multicomponent synthesis of heterocycles
    Javahershenas, Ramin
    Nikzat, Sahand
    ULTRASONICS SONOCHEMISTRY, 2024, 102
  • [4] Ultrasound-assisted oxidative-adsorptive desulfurization using highly acidic graphene oxide as a catalyst-adsorbent
    Abdi, G.
    Ashokkumar, M.
    Alizadeh, A.
    FUEL, 2017, 210 : 639 - 645
  • [5] Ultrasound-assisted synthesis and characterization of polymethyl methacrylate/reduced graphene oxide nanocomposites
    Poddar, Maneesh Kumar
    Pradhan, Sushobhan
    Moholkar, Vijayanand S.
    Arjmand, Mohammad
    Sundararaj, Uttandaraman
    AICHE JOURNAL, 2018, 64 (02) : 673 - 687
  • [6] A Review on Green Synthesis and Biological Activities of Medicinally Important Nitrogen and Oxygen Containing Heterocycles
    Gulati, Susheel
    Singh, Rajvir
    Sangwan, Suman
    CURRENT ORGANIC CHEMISTRY, 2022, 26 (20) : 1848 - 1894
  • [7] Ultrasound-assisted synthesis of α-aminophosphonates using nano ZnO catalyst: evaluation of their anti-diabetic activity
    Basha, Meson Haji
    Subramanyam, Chennamsetty
    Malar, C. Gladis Raja
    Kumar, Katare Kiran
    Seelam, Mohan
    Lakshmi, Vedula Naga
    Rao, Kammela Prasada
    ORGANIC COMMUNICATIONS, 2024, 17 (04) : 249 - 264
  • [8] Gold and silver assisted synthesis of five-membered oxygen and nitrogen containing heterocycles
    Kaur, Navjeet
    SYNTHETIC COMMUNICATIONS, 2019, 49 (12) : 1459 - 1485
  • [9] Ultrasound-Assisted Synthesis of Some Novel 1,3-Diarylpyrazolyl α-Aminophosphonates Conjugated with Nitrogen Heterocycles as Antifungal Agents using CdI2 Nanoparticles as an Efficient Catalyst
    Hussien, M.
    Ali, T. E.
    Sayed, I. E. El
    Abdelaleem, A. H.
    Torkey, H. M.
    Assiri, M. A.
    Yahia, I. S.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (07) : 1214 - 1223
  • [10] Ultrasound-Assisted Synthesis of Some Novel 1,3-Diarylpyrazolyl α-Aminophosphonates Conjugated with Nitrogen Heterocycles as Antifungal Agents using CdI2 Nanoparticles as an Efficient Catalyst
    M. Hussien
    T. E. Ali
    I. E. El Sayed
    A. H. Abdelaleem
    H. M. Torkey
    M. A. Assiri
    I. S. Yahia
    Russian Journal of Organic Chemistry, 2023, 59 : 1214 - 1223