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Design and synthesis of novel enantiopure Bis(5-Isoxazolidine) derivatives: insights into their antioxidant and antimicrobial potential via in silico drug-likeness, pharmacokinetic, medicinal chemistry properties, and molecular docking studies.

Authors
  • Al-Adhreai, Arwa1
  • ALSaeedy, Mohammed2
  • Alrabie, Ali1
  • Al-Qadsy, Inas1
  • Dawbaa, Sam3
  • Alaizeri, ZabnAllah M4
  • Alhadlaq, Hisham A4
  • Al-Kubati, Abdulrahman5
  • Ahamed, Maqusood4
  • Farooqui, Mazahar1
  • 1 Department of Chemistry, Maulana Azad of Arts, Science and Commerce, Aurangabad, 431004, India. , (India)
  • 2 Department of Chemistry, Faculty of Science, Anadolu University, 26470, Eskişehir, Turkey. , (Turkey)
  • 3 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, 26470, Eskişehir, Turkey. , (Turkey)
  • 4 Department of Physics and Astronomy, College of Science, King Saud University, Riyadh, 11451, Saudi Arabia. , (Saudi Arabia)
  • 5 Department of Chemistry "Giacomo Ciamician" University of Bologna, 40126, Bologna, BO, Italy. , (Italy)
Type
Published Article
Journal
Heliyon
Publisher
Elsevier
Publication Date
Jun 01, 2022
Volume
8
Issue
6
Identifiers
DOI: 10.1016/j.heliyon.2022.e09746
PMID: 35800717
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

A series of novel compounds, mono-5-isoxazolidines, and bis (5-isoxazolidines) derivatives, were prepared as bicycloadducts. The new series of isoxazolidines were designed and synthesized via 1,3-dipolar cycloaddition reaction of nitrones with 3,9-Divinyl-2,4,8,10-tetra oxaspiro (5-5) undecane in the context of new antimicrobial and antioxidant drugs discovery and were fully characterized by FT-IR, 13C-NMR, and 1H-NMR spectroscopy. The physicochemical properties of all the novel cycloadducts, like bioactivity score and lipophilicity, were predicted using calculative methods. Similarly, the pharmacokinetic properties such as metabolism, absorption, distribution, and excretion (ADME) were also predicted. Most of the tested compounds exhibited antimicrobial properties to varying degrees against various bacterial species, including the Gram-negative bacteria Pseudomonas aeruginosa and Escherichia coli, and the Gram-positive bacteria Streptococcus pyogenus and Staphylococcus aureus, Antifungal properties were also observed against the tested fungi like Candida albicans, Aspergillus niger, and Aspergillus clavatus. The activity data exhibited that most compounds have high activity as compared to the standard drugs. In the range of graded doses, the results of some selected compounds revealed that some are high antioxidants while others are moderate or weak antioxidants. As evidenced by the molecular docking studies, the synthesized compounds showed good binding mode better than a standard drug, against the protein of a Pantothenate Synthetase enzyme (PDB-2X3F). © 2022 The Authors.

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