NewN-phenylacetamide-incorporated 1,2,3-triazoles: [Et₃NH][OAc]-mediated efficient synthesis and biological evaluation

Abstract

A facile, highly efficient, and greener method for the synthesis of new 1,4-disubstituted-1,2,3-triazoles was conducted using [Et 3 NH][OAc] as a medium by the implementation of ultrasound irradiation via click chemistry, affording excellent yields. The present synthetic method exhibited numerous advantages such as mild reaction conditions, excellent product yields, minimal chemical waste, operational simplicity, shorter reaction time, and a wide range of substrate scope. The synthesized compounds were further evaluated for in vitro antifungal activity against five fungal strains, and some of the compounds displayed equivalent or greater potency than the standard drug. A molecular docking study against the modelled three-dimensional structure of cytochrome P450 lanosterol 14a-demethylase was also performed to understand the binding affinity and binding interactions of the enzyme. Furthermore, the synthesized compounds were evaluated for DPPH radical scavenging activity and antitubercular activity against Mycobacterium tuberculosis H37Rv strain. Fig. 2 1,2,4-Triazole-based marketed antifungal drugs.Scheme 1 Synthesis of alkynes 2a-c and 2-azido-N-phenylacetamides 5a-g. Reagents and conditions: (a) propargyl bromide, K 2 CO 3 , DMF, 2 h, 90-95%; (b) chloroacetyl chloride, NEt 3 , CH 2 Cl 2 , 0 C to rt, 3-5 h, 85-95%; (c) NaN 3 , toluene, reflux, 5-7 h, 88-96%. Scheme 2 Standard model reaction. This journal isScheme 3 Synthesis of 1,4-disubstituted-1,2,3-triazole 6a via the one-pot three-component click reaction. This journal isScheme 4 Synthesis of 1,4-disubstituted-1,2,3-triazole derivatives 6a-g, 7a-g, and 8a-g.22084 | RSC Adv., 2019, 9, 22080-22091This journal is Fig. 4 Binding pose and molecular interactions in the active sites of C. albicans lanosterol 14a-demethylase: (a) 8f and (b) 8g.22086 | RSC Adv., 2019,9,[22080][22081][22082][22083][22084][22085][22086][22087][22088][22089][22090][22091] This journal is

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...…”

A Recent Overview of 1,2,3-Triazole-Containing Hybrids as Novel Antifungal Agents: Focusing on Synthesis, Mechanism of Action, and Structure-Activity Relationship (SAR)

“…ese compounds were assessed in vitro for antifungal activity against five different fungus species: Aspergillus niger, Aspergillus flavus, Fusarium oxysporum, Cryptococcus neoformans, and Candida albicans. Some compounds have the same or greater power compared to the reference drug (Miconazole) (Figure 18) [83]. Aryloxy-linked dimeric 1,2,3-triazoles from azides and bis(prop-2-yn-1-yloxy)benzene were synthesized by Deshmukh et al [84] using a Cu(I)-catalyzed click chemistry approach with good to excellent yields.…”

New N‐phenylacetamide‐linked 1,2,3‐triazole‐tethered coumarin conjugates: Synthesis, bioevaluation, and molecular docking study

“…several biological activities. [52][53][54][55] On the basis of these reports and The starting materials, 2-azido-N-phenylacetamides 3a-g, were prepared by a previously reported method [45,51] from corresponding anilines in excellent yields (Scheme 1). The 7-hydroxy-4-methyl coumarin 5a has been synthesized via acid-catalyzed Pechmann condensation between resorcinol and ethyl acetoacetate in 80% yield (Scheme 1).…”

“…In continuation of our previous works [ 40,42–51 ] on the synthesis and biological evaluation of heterocycles, and the significance of coumarin and 1,2,3‐triazole moieties in a single molecular framework, herein, we would like to report the design and syntheses of new N ‐phenylacetamide‐linked coumarin–triazole conjugates by using the molecular hybridization approach (Figure 3).…”