Design, Synthesis, and Antifungal Activity of Novel Aryl-1,2,3-Triazole-β-Carboline Hybrids

Abstract

The copper catalytic azide and terminal alkyne cycloaddition reaction, namely “click chemistry”, gives a new and convenient way to create l,4-disubstitutd-l,2,3-triazoles. In this work, 2-pyrrolecarbaldiminato–Cu(II) complexes were established as efficient catalysts for the three-component 1,3-dipolar cycloaddition reaction of arylboronic acid and sodium azide (NaN3) with terminal alkynes in ethanol at room temperature to 50 °C, 1,4-disubstituted 1,2,3-triazoles were synthesized. Following the optimized protocol, two series of new aryl-1,2,3-triazole-β-carboline hybrids have been designed and synthesized, and the chemical structures were characterized by 1H NMR, 13C NMR, and high-resolution mass spectrometry (HRMS). All of the target compounds were evaluated in vitro for their antifungal activity against Rhizoctorzia solani, Fusarium oxysporum, Botrytis cinerea Pers., sunflower sclerotinia rot, and rape sclerotinia rot by mycelia growth inhibition assay at 50 μg/mL. The antifungal evaluation of the novel hybrids showed that, among the tested compounds, 5a, 5b, 5c, and 9b showed good antifungal activity against sunflower sclerotinia rot. Specifically, compound 9b also exhibited high broad-spectrum fungicidal against all the tested fungi with inhibition rates of 58.3%, 18.52%, 63.07%, 84.47%, and 81.23%. However, for F. oxysporum, all the target compounds showed no in vitro antifungal activities with an inhibition rate lower than 20%. These results provide an encouraging framework that could lead to the development of potent novel antifungal agents.

Design, Synthesis, and Antimicrobial Activities of 1,2,3-Triazole Glycoside Clickamers

“…Therefore, special concern should be devoted to the development of new antimicrobial agents, possessing completely different chemical structures, and working with different modes of actions. The Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction offers a versatile synthetic access to the 1,2,3-triazole heterocycle derivatives, which are associated with a wide spectrum of pharmacological activities, including antimycobacterial [18][19][20][21], antitubercular [22][23][24][25], anticancer [26][27][28][29], antiviral [30][31][32][33][34], antidiabetic [35][36][37][38], antifungal [39][40][41][42], anti-HIV [43][44][45][46], anti-inflammatory [47][48][49][50], antimalarial [51][52][53][54], anti-oxidant [55][56][57][58], anti-proliferative [59][60][61][62] properties. The 1...…”

Copper-Catalyzed Aminoboration from Hydrazones To Generate Borylated Pyrazoles

“…This aminoboration method is tolerant of a variety of functional groups and generates exclusively the 4-borylated regioisomer in one synthetic step, without the need to preform the heterocyclic core. Products of this reaction are building blocks toward potent medicinal scaffolds that exhibit a full spectrum of biological activities, such as antimicrobial, antifungal, antiinflammatory, anticancer, and many others . Pyrazoles are present in several FDA-approved drugs, for example celecoxib (Celebrex), sildenafil citrate (Viagra), tepoxalin (Zubrin), and also in pesticides .…”

Synthesis, Insecticidal, Fungicidal Activities and Structure–Activity Relationships of Tschimganin Analogs

“…The antifungal activities of the synthesized compounds were performed according to previously reported procedures [19]. The fungicidal activities of the target compounds against C. lagenarium (Pass.)…”