Click chemistry inspired synthesis of piperazine-triazole derivatives and evaluation of their antimicrobial activities

Abstract

A series of novel piperazine-1,2,3-triazole derivatives, which entailed the bioisosteric replacement of the imidazole moiety and hybridization of two drug scaffolds was prepared by employing the regioselective copper (I)-catalysed azide-alkyne 1,3-dipolar cycloaddition reaction. The synthesized compounds were evaluated for antibacterial activities against Gram-negative (E. Coli and P. Putida), Gram-positive S. Aureus bacteria and fungicidal activities against F. oxysporum, F. gramillarium and F. monalliforme fungi. Compound 7ac 0 exhibited moderate but promising antibacterial activity against Gram-negative bacteria and fungicidal activity against F. oxysporum and F. gramillarium.

Synthesis, Characterization, Antimicrobial Activity and in Silico Studies of Some Phenyl, Furyl and 1H‐1,2,4‐Triazole Substituted Benzyl and Alkyl Ethers

“…Yield: 52%, oily. 1 H NMR (400 MHz, CDCl 3 ): δ 4.12 (1H, d, J = 11.6 Hz), 4.25 (1H, dd, J = 3.86, 14.0 Hz), 4.34 (1H, dd, J = 8.6, 14.0 Hz), 4.41 (1H, d, J = 11.6 Hz), 4.67 (1H, dd, J = 4.0, 8.5 Hz), 6.97-7.04 (2H, m), 7.17-7.37 (8H, m), 7.87 (1H, s), 8.07 (1H, s). 13…”

“…Yield: 50%, oily. 1 Hz), 6.38 (1H, dd, J = 2.0, 3.2 Hz), 7.06 (2H, dd, J = 2.4, 7.2 Hz), 7.24-7.30 (3H, m), 7.47 (1H, d, J = 1.6 Hz), 7.91 (1H, s), 8.08 (1H, s). 13…”

“…This situation is compelling modern science to consistently produce novel antifungals. [1] Triazoles are five-membered aromatic heterocyclic compounds having two carbon and three nitrogen atoms. Due to the binding with enzymes and receptors in biological systems, they have various biological activities.…”

CuAAC-ensembled 1,2,3-triazole-linked isosteres as pharmacophores in drug discovery: review

“…The studies prove that compound 20a containing electron-withdrawing groups on phenyl ring has better antibacterial activity and in the case of no electron-withdrawing groups on the phenyl ring, it acts as an anti-fungal 20b. 41 Mono and bis-aryloxy linked coumarinyl triazoles 21 act as anti-tubercular agent and the results indicated that bis-triazoles are more active than monotriazoles. The activity of these compounds is regulated by the ability of 1,2,3-triazole and the phenoxy moiety to form hydrogen bonds with the protein at the site of the receptor.…”

Synthesis, antibacterial, and antioxidant activities of naphthyl‐linked disubstituted 1,2,3‐triazoles

“…In recent years, chemical and biological usefulness of heterocyclic compounds attracted attention of chemist in form of pharmaceuticals, agrochemicals, polymers, dyes, etc . Triazole, a five‐membered heterocycle is key important, as its derivatives exhibited various biological activities such as antibacterial, antimalarial, antitubercular, anticancer, antiparasitic, antileishmanial, antioxidant, anti‐inflammatory, antidepressant, antiviral, etc. The 1,2,3‐triazole derivatives play an intriguing role in the development of new drugs, as effectively exerts various non‐covalent interactions which improves the solubility and the ability of binding to bimolecular targets …”