1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Abstract

A B S T R A C TThe 1,2,3-triazole ring is a major pharmacophore system among nitrogen-containing heterocycles. These fivemembered heterocyclic motifs with three nitrogen heteroatoms can be prepared easily using 'click' chemistry with copper-or ruthenium-catalysed azide-alkyne cycloaddition reactions. Recently, the 'linker' property of 1,2,3-triazoles was demonstrated, and a novel class of 1,2,3-triazole-containing hybrids and conjugates was synthesised and evaluated as lead compounds for diverse biological targets. These lead compounds have been demonstrated as anticancer, antimicrobial, anti-tubercular, antiviral, antidiabetic, antimalarial, anti-leishmanial, and neuroprotective agents. The present review summarises advances in lead compounds of 1,2,3-triazolecontaining hybrids, conjugates, and their related heterocycles in medicinal chemistry published in 2018. This review will be useful to scientists in research fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology. Chemistry: synthesis and properties of the 1,2,3-triazolesThe general synthetic route of 1,2,3-triazoles using click chemistry is described in Scheme 1A. The most popular route to 1,2,3-triazoles is Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition, which is the https://doi.

Polyvinylpolypyrrolidone‐Stabilized Copper Nanoparticles as an Efficient and Recyclable Heterogeneous Catalyst for the Click of 1,2,3‐Triazoles in Water

“…Since its discovery by Huisgen, the 1,3‐dipolar cycloaddition reaction between azide and alkyne has been applied for the syntheses of 1,4‐ and 1,5‐disubstituted‐1,2,3‐triazoles, which in turn have been served as important and key structural motifs in several applications ranging from biology to material sciences . However, the Huisgen reaction was characterized by being carried out at high temperatures, with a low rate and providing a mixture of both 1,4‐ and 1,5‐disubstituted‐1,2,3‐triazoles as regioisomers .…”

“…Since its discovery by Huisgen, the 1,3-dipolar cycloaddition reaction between azide and alkyne has been applied for the syntheses of 1,4-and 1,5-disubstituted-1,2,3-triazoles, which in turn have been served as important and key structural motifs in several applications ranging from biology to material sciences. [1][2][3][4][5][6][7][8][9][10] However, the Huisgen reaction was characterized by being carried out at high temperatures, with a low rate and providing a mixture of both 1,4-and 1,5-disubstituted-1,2,3-triazoles as regioisomers. [11] Subsequently, an improved synthetic procedure involving copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction has been introduced under the context of the click chemistry concept by the groups of Sharpless and Meldal in 2002.…”

Synthesis of Camphecene and Cytisine Conjugates Using Click Chemistry Methodology and Study of Their Antiviral Activity

“…Oxygen‐containing monoterpenes proved to be efficient against influenza virus and Marburg virus . Although the 1,2,3‐triazole moiety does not exist in nature, it has attracted interest as a candidate anticancer drug, particularly for the production of ‘1,2,3‐triazole‐natural compound’ hybrids . The introduction of 1,3‐thiazole heterocycle into camphor molecule leads to compounds showing antibacterial and antifungal activity …”

“…[7] Although the 1,2,3-triazole moiety does not exist in nature, it has attracted interest as a candidate anticancer drug, particularly for the production of '1,2,3-triazole-natural compound' hybrids. [8] The introduction of 1,3-thiazole heterocycle into camphor molecule leads to compounds showing antibacterial and antifungal activity. [9] It was shown previously that a product resulting from the reaction of camphor and aminoethanol and called camphecene exhibits a wide spectrum of antiviral activity and low toxicity.…”

A Suitable Functionalization of Nitroindazoles with Triazolyl and Pyrazolyl Moieties via Cycloaddition Reactions

“…1,3-Dipolar cycloadditions have been successfully exploited as a facile route for the construction of five-membered heterocyclic rings [1,2]. These reactions are considered relevant alternatives to heterocyclic classic routes and allows one to install biologically significant functionalities like triazole and pyrazoline units in different scaffolds in a single step [3][4][5][6][7][8][9]. An attractive approach giving rise to substituted triazole derivatives is based on the 1,3-dipolar cycloaddition of azides to terminal alkynes catalysed by copper(I), the so-called Copper(I)-catalysed azide-alkyne (CuAAC) reaction [10][11][12].…”