Ultrasound‐assisted efficient synthesis of polyfunctional 1,2,4‐triazoles as novel antibacterial and antioxidant agents

Abstract

Novel 4,5‐diphenyl‐1H‐imidazol‐1‐yl‐1H‐1,2,4‐triazole derivatives were synthesized using a facile and highly efficient, one‐pot, four‐component procedure in the presence of KHSO4 as an acidic catalyst under ultrasonic irradiations in short reaction times (10–25 min) and good to excellent yields (70–96%). The synthesized compounds were screened for their antibacterial activities against Gram‐negative (Escherichia coli, Pseudomonas aeruginosa) and Gram‐positive (Bacillus subtilis, Micrococcus luteus) bacteria, and their antioxidant activity was also evaluated. Some of the products showed potential antibacterial and high antioxidant activities.

Valorization of natural clay as an ecological catalyst in the regioselective synthesis of some heterocyclic compounds based on 1,2,3-triazoles

“…The characterization techniques used in this work were: X-ray diffraction, IR spectroscopy for ecological catalysts. 1 HNMR, 13 CNMR, Infrared (IR), and Ultraviolet spectroscopy for triazoles. LC-MS analyses evaluated the molecular masses of synthesized triazoles.…”

“…This report presents the triazoles compounds with a cycle containing five atoms; three are nitrogen, placed in the 1,2,3 position of the cycle. These triazoles compounds have a several biological activities: Antiproliferative [9], anti-inflammatory [10], antitubercular [11], tyrosinase inhibitory [12], antioxidant [13,14] and antibacterial [15]. For this reason, the synthesis of triazoles was considerably developed.…”

“…Analysis sectionBenzyl azide (1b): yield 94%, IR (ν cm -1 ): 3042(Car-H), 2986-2869 (CH2), 2093 (N3), 1453 1. H NMR (CDCl3): δ 4.38 (s, 2H) and 7.35-7.46 (m, 5H) 13. C NMR (CDCl3): δ 55.2, 128.7, 129.1, 129.3, 135.9.…”

“…Ethyl azidoacetate (2b): yield 84%, IR (ν cm -1 ): 2992-2866 (CH2), 2100 (N3), 1737 (C=O) 1. H NMR (CDCl3): δ 1.27 (t, 3H, J=7.1Hz), 3.83 (s, 2H) and 4.22 (q, 2H, J= 7.1Hz) 13. C NMR (CDCl3): δ 14.2, 50.1, 61.0 and 167.4.…”

Recent Synthetic and Biological Developments on 1,2,4‐Triazolopyrimidines

“…Some of drug candidates with 1,2,4‐triazole moiety has been shown in Figure 1 like antifungal (voriconazole, fluconazole, isavuconazole, hexaconazole), anticancer (anastrazole), antiviral (ribavirin), antiestrogen (letrozole), antimigraine (rizatriptan), sedative & hypnotic (rilmazafone), anticonvulsant (loreclezole), antidepressant (estazolam, alprazolam, triazolam, etizolam, trazodone) etc. Furthermore, 1,2,4‐triazole nucleus has been recently acknowledged with ergastic and multifarious therapeutic properties such as anti‐inflammatory, [1] anticancer, [2] antibacterial, [3] antiherbicide, [4] anticonvulsant, [5] antifungal, [6] antitubercular, [7] antileishmanial, [8] anti‐tubulin, [9] antiproliferative, [10] antioxidant, [11] neuroprotectant, [12] antimalarial, [13] corrosion inhibitor, [14] cholinesterase inhibitor [15] and carbonic anhydrase (CA) II inhibitor [16] . The key characteristics features of low toxicity, high bioavailability, good pharmacokinetic property, less adverse effects along with impendence of non‐covalent interaction associated to triazole nucleus significantly enhance its solubility and binding capacity with enzyme or receptor target.…”