Halo-1,2,3-triazole: valuable compounds to access biologically relevant molecules

Chembiochem. 2024 Mar 30:e202400150. doi: 10.1002/cbic.202400150. Online ahead of print.ABSTRACT1,2,3-triazole is an important building block in organic chemistry. It is also now well known as bioisostere for various functions, such as the amide or the ester bond, positioning it as key pharmacophore in medicinal chemistry and it has found applications in various fields including life sciences. Attention was first focused on the synthesis of 1,4-disubstituted 1,2,3-triazole molecules but 1,4,5-trisubstituted 1,2,3-triazoles have emerged as valuable molecules due to the possibility to expand the structural modularity. In the last decade, methods mainly derived from the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction have been developed to access halo-triazole compounds and have been applied to nucleosides, carbohydrates, peptides and proteins. In addition, late-stage modification of halo-triazole derivatives by metal-mediated cross-coupling or halo-exchange reactions offers the possibility to access highly functionalized molecules that can be used as a tools for chemical biology. This review summarizes the synthesis, the functionalization, and the applications of 1,4,5-trisubstituted halo-1,2,3-triazoles in biologically relevant molecules.PMID:38554039 | DOI:10.1002/cbic.202400150
Source: Chembiochem - Category: Biochemistry Authors: Source Type: research