Green Biocatalyst for Ultrasound-Assisted Thiazole Derivatives: Synthesis, Antibacterial Evaluation, and Docking Analysis

被引:8
作者
Hussein, Ahmed M. [1 ,2 ]
Gomha, Sobhi M. [7 ]
Abd El-Ghany, Nahed A. [5 ]
Zaki, Magdi E. A. [3 ]
Farag, Basant [4 ]
Al-Hussain, Sami A. [3 ]
Sayed, Abdelwahed R. [1 ]
Zaki, Yasser H. [1 ]
Mohamed, Nadia A. [5 ,6 ]
机构
[1] Beni Suef Univ, Fac Sci, Chem Dept, Bani Suwayf 62511, Egypt
[2] Shaqra Univ, Coll Sci & Humanities Al Quwaiiyah, Chem Dept, Shaqra 11911, Saudi Arabia
[3] Imam Mohammad Ibn Saud Islamic Univ IMSIU, Fac Sci, Dept Chem, Riyadh 11623, Saudi Arabia
[4] Zagazig Univ, Fac Sci, Dept Chem, Zagazig 44519, Egypt
[5] Cairo Univ, Fac Sci, Dept Chem, Giza 12613, Egypt
[6] Qassim Univ, Dept Chem, Coll Sci, Buraydah 51452, Saudi Arabia
[7] Islamic Univ Madinah, Fac Sci, Dept Chem, Madinah 42351, Saudi Arabia
来源
ACS OMEGA | 2024年 / 9卷 / 12期
关键词
ONE-POT SYNTHESIS; ANTIMICROBIAL ACTIVITY; MOLECULAR DOCKING; CYTOTOXICITY EVALUATION; CHITOSAN; CATALYST; CHITIN; PERMEABILITY; PATHOGENS; NITRILES;
D O I
10.1021/acsomega.3c07785
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The catalytic activity of chitosan (Cs) and grafted Cs led to the preparation of terephthalohydrazide Cs Schiff's base hydrogel (TCsSB), which was then investigated as an eco-friendly biocatalyst for synthesizing novel thiazole derivatives. TCsSB exhibited greater surface area and higher thermal stability compared to Cs, making it a promising eco-friendly biocatalyst. We synthesized two novel series of thiazoles via the reaction of 2-(2-oxo-1,2-diphenylethylidene) hydrazine-1-carbothioamide with various hydrazonoyl chlorides and 2-bromo-1-arylethan-1-ones, employing ultrasonic irradiation and using TCsSB as a catalyst. A comparative study between Cs and TCsSB revealed higher yields than TCsSB. The methodology offered advantages such as mild reaction conditions, quick reaction times, and high yields. TCsSB could be reused multiple times without a significant loss of potency. The chemical structures of the newly synthesized compounds were verified through IR, H-1 NMR, C-13 NMR, and MS analyses. Six synthesized compounds were assessed for their in vitro antibacterial effectiveness by establishing the minimum inhibitory concentration against four distinct bacterial strains. The docking analyses revealed favorable binding scores against several amino acids within the selected protein (PDB Code-1MBT) for these compounds, with compound 4c exhibiting particularly noteworthy binding properties. Additionally, the in silico ADME parameter estimation for all compounds indicated favorable pharmacological properties for these compounds.
引用
收藏
页码:13666 / 13679
页数:14
相关论文
共 82 条
  • [21] Chopra H., 2018, PHARM INNOVATION J, V7, P311
  • [22] Ultrasound-Promoted Copper-Catalyzed Azide-Alkyne Cycloaddition
    Cravotto, Giancarlo
    Fokin, Valery V.
    Garella, Davide
    Binello, Arianna
    Boffa, Luisa
    Barge, Alessandro
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (01): : 13 - 15
  • [23] SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules
    Daina, Antoine
    Michielin, Olivier
    Zoete, Vincent
    [J]. SCIENTIFIC REPORTS, 2017, 7
  • [24] Metal-Free One-Pot Synthesis of 2-(2-Hydrazinyl) Thiazole Derivatives Using Graphene Oxide in a Green Solvent and Molecular Docking Studies
    Das, Arindam
    Dey, Sovan
    Chakraborty, Sumit
    Barman, Anup
    Yadav, Ram Naresh
    Gazi, Rabiul
    Jana, Madhurima
    Hossain, Md Firoj
    [J]. CHEMISTRYSELECT, 2021, 6 (36): : 9552 - 9558
  • [25] Chitosan: a highly efficient renewable and recoverable bio-polymer catalyst for the expeditious synthesis of α-amino nitriles and imines under mild conditions
    Dekamin, Mohammad G.
    Azimoshan, Mojtaba
    Ramezani, Leila
    [J]. GREEN CHEMISTRY, 2013, 15 (03) : 811 - 820
  • [26] REINFORCEMENT OF ANTIMICROBIAL ACTIVITY AND SWELLING ABILITY OF STARCH-G-POLY 4-ACRYLAMIDOBENZOIC ACID USING CHITOSAN NANOPARTICLES
    El-Ghany, Nahed A. Abd
    Aziz, Mohamed S. Abdel
    Abdel-Aziz, Marwa M.
    Mahmoud, Zain M.
    [J]. CELLULOSE CHEMISTRY AND TECHNOLOGY, 2023, 57 (7-8): : 803 - 813
  • [27] Evaluation of the antimicrobial and anti-biofilm activity of novel salicylhydrazido chitosan derivatives impregnated with titanium dioxide nanoparticles
    Elmehbad, Noura Y.
    Mohamed, Nadia A.
    Abd El-Ghany, Nahed A.
    [J]. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2022, 205 : 719 - 730
  • [28] Terephthalohydrazido cross-linked chitosan hydrogels: synthesis, characterization and applications
    Elmehbad, Noura Y.
    Mohamed, Nadia A.
    [J]. INTERNATIONAL JOURNAL OF POLYMERIC MATERIALS AND POLYMERIC BIOMATERIALS, 2022, 71 (13) : 969 - 982
  • [29] Native and modified chitosan-based hydrogels as green heterogeneous organocatalysts for imine-mediated Knoevenagel condensation
    Franconetti, A.
    Dominguez-Rodriguez, P.
    Lara-Garcia, D.
    Prado-Gotor, R.
    Cabrera-Escribano, F.
    [J]. APPLIED CATALYSIS A-GENERAL, 2016, 517 : 176 - 186
  • [30] Probing the links between in vitro potency, ADMET and physicochemical parameters
    Gleeson, M. Paul
    Hersey, Anne
    Montanari, Dino
    Overington, John
    [J]. NATURE REVIEWS DRUG DISCOVERY, 2011, 10 (03) : 197 - 208