Synthesis, Antibacterial and Antifungal Activities of Novel 1,2,4‐Triazolium Derivatives

Abstract

A series of novel 1,2,4-triazolium derivatives was synthesized starting from commercially available 1H-1,2,4-triazole, 2,4-dichlorobenzyl chloride, or 2,4-difluorobenzyl bromide. Their antibacterial and antifungal activities were evaluated against Staphylococcus aureus ATCC 29213, Escherichia coli ATCC 25922, Bacillus proteus, Bacillus subtilis, Pseudomonas aeruginosa, Candida albicans ATCC 76615, and Aspergillus fumigatus. All structures of the new compounds were confirmed by NMR, IR, and MS spectra, and elemental analyses. The antimicrobial tests showed that most of synthesized triazolium derivatives exhibit significant antibacterial and antifungal activities in vitro. 1-(2,4-Difluorobenzyl)-4-dodecyl-1H-1,2,4-triazol-4-ium bromide and 1-(2,4-Dichlorobenzyl)-4-dodecyl-1H-1,2,4- triazol-4-ium bromide were the most potent compounds against all tested strains with the MIC values ranging from 1.05 to 8.38 microM. They exhibited much stronger activities than the standard drugs chloramphenicol and fluconazole which are in clinical use. The results also showed that the antimicrobial activities of triazolium derivatives depend upon the type of substituent, the length of the alkyl chain, and the number of triazolium rings.

Pharmacological activities of Triazole analogues as antibacterial, antifungal, antiviral agents

“…The 4-(5-nitro-2-furfurylidene) amino-3-mercapto-5-(substituted)-1,2,4-triazoles (27) 49 and some 1,2,4-triazoles (28) were exhibited antibacterial activity 50 . Antifungal activity of some 1,2,4-triazole has been shown, the 4-substituted-5-aryl-1,2,4-triazoles (29) 51 and 1,2,4-triazolium derivatives (30) were exhibited antifungal activity 52 . Some novel mannich bases derived from 3-(4,6-disubstituted-2-thiomethyl-pyrimidyl)-4-amino-5-mercapto-1,2,4-triazoles (31) 53 and 1,2,4-triazole derivatives (32) were revealed antifungal activity 54 .…”

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

“…The mono-triazole 206 reacted with a series of dihalides, which were commercially available or were prepared by conventional method via bromination of the corresponding precursors, via Nquaternization to readily produce bis-triazolium 207 in good yields of 74-95%. Notably, the reaction temperature obviously affected the formation of target compounds, and only when the temperature was controlled above 80 °C, this reaction would proceed smoothly (Scheme 90) [280,281].…”

Novel 1,2,3-triazolium-functionalized starch derivatives: Synthesis, characterization, and evaluation of antifungal property

“…Many studies from the past had reported that the length of the alkyl groups was an important determinant of antifungal activity (Chandrika, Shrestha, Ngo, & Garneau-Tsodikova, 2016;Luo et al, 2009). Therefore, the effect of the length of the alkyl groups in 1,2,3-triazolium-functionalized starch derivatives on antifungal activity is also evaluated in this paper.…”