TY - JOUR
T1 - Synthesis of 1,2,3-triazole-thymol derivatives as potential antimicrobial agents
AU - Addo, Justice Kwaku
AU - Owusu-Ansah, Ernest
AU - Dayie, Nicholas T.K.D.
AU - Cheseto, Xavier
AU - Torto, Baldwyn
N1 - Publisher Copyright:
© 2022 The Author(s)
PY - 2022/10
Y1 - 2022/10
N2 - 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 (1H-NMR, 13C-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, Klebsiella 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)-1H-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.
AB - 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 (1H-NMR, 13C-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, Klebsiella 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)-1H-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.
KW - Ampicillin
KW - Antibacterial activity
KW - Essential oil
KW - Monoterpenoid
KW - Thymol
KW - Triazole
UR - http://www.scopus.com/inward/record.url?scp=85139294410&partnerID=8YFLogxK
U2 - 10.1016/j.heliyon.2022.e10836
DO - 10.1016/j.heliyon.2022.e10836
M3 - Article
AN - SCOPUS:85139294410
SN - 2405-8440
VL - 8
JO - Heliyon
JF - Heliyon
IS - 10
M1 - e10836
ER -