Synthesis, Characterization, and Antimicrobial Potential of Some 1,4-Disubstituted 1,2,3-Bistriazoles

Abstract

A convenient synthesis of some new 1,4-disubstituted 1,2,3-bistriazoles (3a-3f, 4a-4f, 6a-6b, 7a-7b) is reported via copper (I) catalyzed Huisgen 1,3-dipolar cycloaddition of various terminal alkynes with 1,4-bis(azidomethyl)benzene and 1,6-diazidohexane. The synthesized compounds were characterized by spectral techniques viz. IR, 1 H NMR, 13 C NMR, HRMS and tested in vitro for antimicrobial potential against Bacillus subtilis, Staphylococcus aureus (Gram positive bacteria), Pseudomonas aeruginosa, Escherichia coli (Gram negative bacteria), Candida albicans and Aspergillus niger (fungi). Among the synthesized 1,4-disubstituted 1,2,3-bistriazoles, compounds 6a, 6b and 7b displayed excellent antimicrobial potential against most of the tested strains.

Triazole-Modified Peptidomimetics: An Opportunity for Drug Discovery and Development

“…The cycloaddition requires Cu(I) or Cu(II) salts in a mixture of tert -butyl alcohol and water or organic solvents at room temperature (Totobenazara and Burke, 2015 ). The above-mentioned technique is one of the examples of click reaction proceeding with high yield and purity, regioselectivity, and comprehensive chemical conversion (Kaushik et al, 2015 ). The 1,2,3-triazole is well-known as a versatile peptidomimetic moiety (Valverde et al, 2012 ).…”

Synthesis of Polyheterocyclic Dimers Containing Restricted and Constrained Peptidomimetics via IMCR-Based Domino/Double CuAAC Click Strategy

“…Examples of bioactive triazole-linked dimeric heterocycles include anticancer agent 1 [5][6][7][8], antimicrobial 2 [9][10][11][12], as well as antioxidants [10] and antipsychotic agents [13] (Figure 1). It is important to note that these compounds have an aliphatic chain spacer between the 1,2,3-triazole rings, probably for lipophilic control, and a heterocyclic component linked to the triazole ring.…”

Synthesis and Antimicrobial Evaluation of (1‐(2‐(Benzyloxy)‐2‐oxoethyl)‐1H‐1,2,3‐triazol‐4‐yl)methyl Benzoate Analogues

“…In order to meet this challenge, 1,2,3‐triazoles emerged as a privileged class of medicinal scaffolds due to its better compatibility. Among N ‐heterocycles, disubstituted 1,2,3‐triazoles have been preferably used as an important pharmacophore owing to the widespread therapeutic importance as antibiofilm , antibiotic , antimicrobial , anticancer , antitubercular , antiinfluenza , antiproliferative , antioxidant , and antimalarial . In addition to the aforementioned medicinal importance, 1,2,3‐triazoles also possess paramount impact in the fields like drug discovery , bioconjugation , and material sciences .…”