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- Title
Synthesis, characterization, and antioxidant activity of thymol-based paracetamol analogues.
- Authors
Sathe, Pradnya S.; Rajput, Jamatsing D.; Gunaga, Shubha S.; Patel, Harun M.; Bendre, Ratnamala S.
- Abstract
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 (4a–e), 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.
- Subjects
THYMOL; LIQUID chromatography-mass spectrometry; ANTIOXIDANT testing; NUCLEAR magnetic resonance; ESSENTIAL oils; MOLECULAR docking
- Publication
Research on Chemical Intermediates, 2019, Vol 45, Issue 11, p5487
- ISSN
0922-6168
- Publication type
Article
- DOI
10.1007/s11164-019-03914-0