Synthesis of 1, 2, 3-triazole-thymol derivatives as potential antimicrobial agents. Issue 10 (October 2022)

• Record Type: Journal Article
• Authors: Addo, Justice Kwaku; Owusu-Ansah, Ernest; Dayie, Nicholas T.K.D.; Cheseto, Xavier; Torto, Baldwyn
• Is Part Of: Heliyon. Volume 8:Issue 10(2022)
• Publication Date: 2022-10
• Subjects: Thymol -- Monoterpenoid -- Essential oil -- Triazole -- Antibacterial activity -- Ampicillin; Research -- Periodicals; Medical sciences -- Periodicals; Natural history -- Periodicals; Social sciences -- Periodicals; Earth sciences -- Periodicals; Physical sciences -- Periodicals; 507.2
• DOI: 10.1016/j.heliyon.2022.e10836
• Languages: English
• ISSNs: 2405-8440

Abstract

Abstract: Background: Thymol as a natural biological template can be modified chemically since the hydroxyl group makes it a candidate for structural modification. Thus, this study incorporated the triazole moiety on thymol and the chlorination of thymol moiety to help improve its biological potency. Materials and methods: A series of ten 1, 2, 3-triazole-thymol derivatives 1–10 were synthesized from thymol, by a click reaction between O-propargyl terminal alkyne of thymol and its chlorothymol with benzyl azide and substituted benzyl azides. Their structures were confirmed by spectroscopic methods ( 1 H-NMR, 13 C-NMR, IR, GC-MS-EI/CI and LC-ESI-QTOF-MS). The Well diffusion method using Müeller-Hinton agar plates was used to demonstrate the antimicrobial activities of the synthesized triazole-thymol derivatives on selected bacterial strains; Escherichia coli ATCC 25922, Staphylococcus aureus ATCC25923, Methicillin resistant S. aureus (MRSA), Pseudomonas aeruginosa ATCC 29853, E. coli ESBL, K l ebsiella pneumoniae NCTC 13438 and Meropenem Resistant E. coli. Results: All the synthesized triazole-thymol derivatives showed significant but variable antibacterial activity against the seven medically important bacterial strains tested. The compound 4-((4-chloro-2-isopropyl-5-methylphenoxy)methyl)-1-(2-nitrobenzyl)-1 H -1, 2, 3triazole (9) demonstrated a higher antibacterial activity with a mean zone of inhibition (38.7 mm) compared with ampicillin as the positive control which gave a zone size of 30.0 mm. In addition, the compound showed a three-fold potency than the parent compound, thymol (11.0 mm) against MRSA at a concentration of 100 μg/ml. Conclusion: These results provide additional evidence of the exploitation of natural products like thymol as leads for drug development against medically important bacterial pathogens. Abstract : Thymol; Monoterpenoid; Essential oil; Triazole; Antibacterial activity; Ampicillins.