How are 1,2,3-triazoles accommodated in helical secondary structures?

Salah, Khoubaib Ben Haj; Das, Sanjit; Ruiz, Nicolás; Andreu, V.; Martinez, Jean; Wenger, Emmanuel; Amblard, Muriel; Didierjean, Claude; Legrand, Baptiste; Inguimbert, Nicolas

doi:10.1039/c8ob00686e

Cited by 23 publications

(28 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Moreover, triazole-linked derivatives were suggested to affect adenosine diphosphate ribosylation biology, 34 and were used widely in peptides to mimic a trans-amide bond, despite their hazardous effects on native peptide activity. 35 In addition, a 1,2,3-triazole core provides diverse pharmacophore properties and hybrids are most commonly considered 'lead compounds' when they contain or are fused by a 1,2,3-triazole ring. Thus, in view of the above factors and the recent focus of researchers on 1,2,3triazole compounds, we have discussed and highlighted the diverse biological activities of the 1,2,3-triazole hybrids, conjugates, and their related compounds as leads in medicinal chemistry, based on articles published in 2018.…”

Section: Introductionmentioning

confidence: 99%

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

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

580

289

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

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

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

580

289

View full text Add to dashboard Cite

show abstract

“…[17,18] It has been also shown that a 1,4-Tz amino acid can replace a dipeptide in an α-helical secondary structure. [19,20] Oligomers of triazole, also called triazolamers have been rarely described. NMR studies of 1,4-Tz trimers (compound 1, Figure 1) and tetramers, where α-amino acid residues linked by 1,4-Tz groups, suggest that these oligomers adopt zigzag conformations which closely mimic peptide β-strands.…”

Section: Introductionmentioning

confidence: 99%

Fluorinated Triazole Foldamers: Folded or Extended Conformational Preferences

Arenas

Milcent

et al. 2021

ChemPlusChem

View full text Add to dashboard Cite

Fluorinated peptidomimetic foldamers are still in their infancy. We report here the easy access to fluorinated triazolamers based on 2-amino-3,3,3-trifluoropropyl-1,4-triazolyl acetic acid (CF 3 À 1,4-Tz) and on aminomethyl-1,4-triazolyl-difluoroacetic acid (1,4-TzÀ CF 2). Both CF 3 À 1,4-Tz and 1,4-TzÀ CF 2 amino acids were efficiently prepared by copper(I)-catalyzed Huisgen 1,3dipolar cycloaddition. Their conformational preferences were studied by 2D NMR analyses and molecular dynamic simulations. Foldamers based on CF 3 À 1,4-Tz amino acids are capable of adopting short multi-stranded β-sheet-like structures that are maintained by electrostatic interactions between the triazole proton and N2 atom of neighboring subunits. On the contrary, foldamers based on 1,4-TzÀ CF 2 units adopt elongated β-strandlike structures, stabilized by electrostatic interaction between fluorine atoms and their neighboring protons.

show abstract

“…In 2003, the first report of a cyclic peptidomimetic was published where a 1,4-substituted 1,2,3-triazole was used as an isostere for the amide bond to obtain molecules which self-assemble into nanotubes [ 25 ]. In the following years, several groups investigated the structural consequences of the incorporation of one or more triazoles on the secondary structure of resulting peptidomimetics such as α-helices and β-sheets [ 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 ]. Another focus of attention was the synthesis and biological evaluation of cyclic peptidomimetics with one or more triazoles in the backbone [ 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 ].…”

Section: Introductionmentioning

confidence: 99%

1,4-Disubstituted 1,2,3-Triazoles as Amide Bond Surrogates for the Stabilisation of Linear Peptides with Biological Activity

2020

View full text Add to dashboard Cite

Peptides represent an important class of biologically active molecules with high potential for the development of diagnostic and therapeutic agents due to their structural diversity, favourable pharmacokinetic properties, and synthetic availability. However, the widespread use of peptides and conjugates thereof in clinical applications can be hampered by their low stability in vivo due to rapid degradation by endogenous proteases. A promising approach to circumvent this potential limitation includes the substitution of metabolically labile amide bonds in the peptide backbone by stable isosteric amide bond mimetics. In this review, we focus on the incorporation of 1,4-disubstituted 1,2,3-triazoles as amide bond surrogates in linear peptides with the aim to increase their stability without impacting their biological function(s). We highlight the properties of this heterocycle as a trans-amide bond surrogate and summarise approaches for the synthesis of triazole-containing peptidomimetics via the Cu(I)-catalysed azide-alkyne cycloaddition (CuAAC). The impacts of the incorporation of triazoles in the backbone of diverse peptides on their biological properties such as, e.g., blood serum stability and affinity as well as selectivity towards their respective molecular target(s) are discussed.

show abstract

How are 1,2,3-triazoles accommodated in helical secondary structures?

Cited by 23 publications

References 51 publications

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

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

Fluorinated Triazole Foldamers: Folded or Extended Conformational Preferences

1,4-Disubstituted 1,2,3-Triazoles as Amide Bond Surrogates for the Stabilisation of Linear Peptides with Biological Activity

Contact Info

Product

Resources

About