Synthesis, characterization, and antioxidant activity of thymol-based paracetamol analogues

  • Pradnya S. Sathe
  • Jamatsing D. Rajput
  • Shubha S. Gunaga
  • Harun M. Patel
  • Ratnamala S. BendreEmail author


Thymol (2-isopropyl-5-methylphenol) is an important monoterpene phenol occurring in the essential oils isolated from Thymus vulgaris, Thymus zygis, Thymus hyemalis, etc. Thymol and its derivatives show various activities such as antioxidant, antiinflammatory, antibacterial, and antifungal effects. In the present study, a set of new benzamide derivatives (4ae), which are structurally similar to paracetamol, were synthesized from thymol using a green synthetic approach and characterized by Fourier-transform infrared (FT-IR) and 1H and 13C nuclear magnetic resonance (NMR) spectroscopies, liquid chromatography–mass spectrometry (LC–MS), and X-ray single-crystallographic analysis for derivative 4c. These derivatives were subjected to antioxidant testing by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and antibacterial testing against five microorganisms. Molecular docking studies of all the compounds indicated that they are good inhibitors of heme oxygenase-1. These results extend the development of thymol-based benzamide scaffolds as promising antioxidant agents.


Benzoylation Thymol Antioxidant activity DPPH Docking Oxygenase-1 



The authors are grateful to UGC SAP (New Delhi) for providing financial assistance.

Supplementary material

11164_2019_3914_MOESM1_ESM.docx (862 kb)
Supplementary material 1 (DOCX 861 kb)


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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  • Pradnya S. Sathe
    • 1
  • Jamatsing D. Rajput
    • 1
  • Shubha S. Gunaga
    • 2
  • Harun M. Patel
    • 3
  • Ratnamala S. Bendre
    • 1
    Email author
  1. 1.Department of Pesticides and Agrochemicals, School of Chemical SciencesKavayitri Bahinabai Chaudhari North Maharashtra UniversityJalgaonIndia
  2. 2.Solid State and Structural Chemistry UnitIndian Institute of ScienceBangaloreIndia
  3. 3.Division of Computer Aided Drug Design, Department of Pharmaceutical ChemistryR. C. Patel Institute of Pharmaceutical Education and ResearchShirpur (Dhule)India

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