1362020-83-4Relevant academic research and scientific papers
Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5-a]quinolines
Alves, Diego,Bach, Mariana F.,Barcellos, Thiago,Lenard?o, Eder J.,Silva, Márcio S.,da Costa, Gabriel P.,de Moraes, Maiara C.
, p. 5044 - 5055 (2020/10/19)
In this work, a one-pot sequential organocatalytic method for the synthesis of fused [1,2,3]triazolo[1,5-a]quinolines through successive cyclization and condensation is presented. In this synthetic strategy, the intermolecular [3+2]-cycloaddition occurs between 1,3-dicarbonyl compounds and o-carbonyl-substituted phenylazide compounds, for the formation of the 1,2,3-triazole intermediates. Subsequently, an intramolecular condensation reaction generates the fused quinoline ring by the new C?C bond formation, giving the products in yields ranging from moderate to excellent. All the reactions were performed using 20 mol% of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as catalyst in the presence of DMSO as solvent at 120 °C for 24 h and tolerate a range of 1,3-dicarbonyl compounds, such as β-keto esters and 1,3-diketones, and o-formyl, o-acetyl or o-benzoyl substituted phenylazide compounds. (Figure presented.).
Design, synthesis, and in vitro biological evaluation of 1 H -1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents targeting virus nucleoprotein
Cheng, Huimin,Wan, Junting,Lin, Meng-I,Liu, Yingxue,Lu, Xiaoyun,Liu, Jinsong,Xu, Yong,Chen, Jianxin,Tu, Zhengchao,Cheng, Yih-Shyun E.,Ding, Ke
, p. 2144 - 2153 (2012/05/04)
The influenza virus nucleoprotein (NP) is an emerging target for anti-influenza drug development. Nucleozin (1) and its closely related derivatives had been identified as NP inhibitors displaying anti-influenza activity. Utilizing 1 as a lead molecule, we successfully designed and synthesized a series of 1H-1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents. One of the most potent compounds, 3b, inhibited the replication of various H3N2 and H1N1 influenza A virus strains with IC 50 values ranging from 0.5 to 4.6 μM. Compound 3b also strongly inhibited the replication of H5N1 (RG14), amantidine-resistant A/WSN/33 (H1N1), and oseltamivir-resistant A/WSN/1933 (H1N1, 274Y) virus strains with IC 50 values in sub-μM ranges. Further computational studies and mechanism investigation suggested that 3b might directly target influenza virus A nucleoprotein to inhibit its nuclear accumulation.
