Ultrasound-assisted synthesis of novel 1,2,3-triazoles coupled diaryl sulfone moieties by the CuAAC reaction, and biological evaluation of them as antioxidant and antimicrobial agents

Abstract

A series of 1,2,3-triazoles coupled diaryl sulfone containing compounds were synthesized by the copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reaction in benign solvents under ultrasound irradiation. In situ formation of azides from α-bromoketones together with the CuAAC reaction in one pot allowed safe handling and good availability of azides for the development of a small library of compounds. The sonication reduced reaction time and increased yields compared to otherwise same conditions. All synthesized compounds were evaluated for antibacterial, antifungal and antioxidant activities. Compounds 3b, 6b and 9e-9g were found to be the most potent antifungal agents with minimal inhibitory concentration (MIC) at 25 μg/mL; moreover other compounds revealed good to moderate antimicrobial activity. Compound 8e showed an excellent antioxidant activity using a DPPH free radical scavenging assay.

1,4-Disubstituted-1,2,3-Triazole Compounds Induce Ultrastructural Alterations in Leishmania amazonensis Promastigote: An in Vitro Antileishmanial and in Silico Pharmacokinetic Study

“…This rule states that molecular mass should be less than 500 Daltons, have no more than five H-bond donors and no more than 10 H-bond acceptors, and a calculated Log P (CLogP) no greater than five (or MLogP > 4. 15). Compounds that violate more than two of Lipinski's rules may encounter problems in the first step of absorption, such as poor solubility and intestinal permeability, interfering in oral bioavailability [46].…”

Combinatorial Chemistry Online Volume 16, Issue 11, November 2014

“…The sonication reduced reaction time and increased yields compared to other conditions. All synthesised compounds were evaluated for antibacterial, antifungal and antioxidant activities and some were found to be potent antifungal or antimicrobial agents [14].…”

A green approach to the synthesis of 2,3‐diaminophenazine using a photocatalytic system of CdFe2O4/TiO2 nanoparticles

“…In continuation of our efforts to develop and discover new efficient classes of bioactive compounds and green synthetic approaches, we will investigate for the first time the use of environmental nanotechnology to overcome preparation limitations using a simple, cost‐effective catalyst such as CdFe 2 O 4 /TiO 2 nanocomposites for the photocatalytic synthesis of 2,3‐diaminophenazine.…”