Synthesis of 1,4-disubstituted 1,2,3-triazole Derivatives Using Click Chemistry and their Src Kinase Activities

Abstract

A series of 1,4-disubstituted 1,2,3-triazole compounds were synthesized through an easy, convenient Cu(I) catalyzed click reaction and evaluated for their Src kinase activity. Compound 3m exhibited significant inhibitory activity against Src Kinase. These results, along with molecular design docking observations, are significant evidence to demonstrate the compound 3m could be optimized as a potential Src kinase inhibitor in further studies.

Triazoles and Their Derivatives: Chemistry, Synthesis, and Therapeutic Applications

“… Lebeau et al (2016) utilized Huisgen 1,3-dipolar cycloaddition of terminal alkynes ( 1) with methyl 2-azidoacetate ( 2) in the presence of Cu(I) and obtained 1,4-disubstituted-1,2,3-triazole derivatives ( 3) in high yields at 25°C ( Supplementary Figure S1B ). The general Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes under heating conditions produces an equal mixture of 1,4- and 1,5-disubstituted isomers ( Huisgen, 1963 ).…”

“…However, the use of Cu(I) catalyst in such a one-pot reaction shows regioselectivity with the formation of only the 1,4-disubstituted isomer and is a model example of click chemistry ( Tornøe et al, 2002 ). Encouragingly, many of the 1,4-disubstituted-1,2,3-triazoles ( 3) showed notable inhibitory activities against Src kinase, and hence could be effective in cancer treatment ( Lebeau et al, 2016 ).…”

Synthesis of a Novel Rhizobitoxine-Like Triazole-Containing Amino Acid

“…1,15,16 Therefore, there is a need for readily accessible stable structural analogues. 1,2,3-Triazole derivatives have gained a recent interest in medicinal chemistry because they are pharmacophores with good stability and high aqueous solubility, [17][18][19][20][21] particularly in the area of peptidomimetics 22 and are readily accessible by the Huisgen 1,3-dipolar cycloaddition involving an alkyne and an azide. [23][24][25][26] In this paper, we describe the synthesis of a new triazole-containing amino acid analogue of rhizobitoxine in protected form (compound (1S,2S)-2) from serine (Figure 2) where the central enol ether linkage in rhizobitoxine is replaced by the robust 1,2,3-triazole linker in such a way that there is no longer β,γ-unsaturation to the amino acid moiety.…”

Theoretical calculations of molecular descriptors for anticancer activities of 1, 2, 3-triazole-pyrimidine derivatives against gastric cancer cell line (MGC-803): DFT, QSAR and docking approaches

“…Compound names of studied 1, 2, 3-triazole-pyrimidine hybrids system obtained from Figure 1. 2008; Giffin et al, 2008;Aher et al, 2009;Wang et al, 2010;De-Simone et al, 2011;Patpi et al, 2012;Yu et al, 2013;Lebeau et al, 2017;Ahmed et al, 2017;Salah et al, 2018;Zaki et al, 2018;Schr€ oder et al, 2019;Romad and Miranda, 2019). Pyrimidine containing sulfa drugs are classified on the basis of substitution and the classification with the respective example of drug is as follows.…”