Design and synthesis of new carbohydrate-lithocholic acid conjugates linked via 1,2,3-triazole rings

Bautista-Hernández, Claudia I.; Negrón‐Silva, Guillermo E.; Santillán, Rosa; Vergara-Arenas, B. I.; Ángeles-Beltrán, Deyanira; Lomas‐Romero, Leticia; Martínez, Diego Luis Valera

doi:10.1016/j.tet.2018.03.008

Cited by 5 publications

(4 citation statements)

References 47 publications

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“…Perez-Martínez and co-workers, recently highlighted the synthesis of a sugar–lithocholic acid conjugate ( 210 ) bridged through a 1,2,3-triazole spacer in fair-to-excellent yields . The synthesis was achieved by clicking dipropargyl ether ( 208 , 1.0 equiv) to methyl 3-azidolithocholate ( 209 , 2.0 equiv) using Cu–Al mixed oxide (as heterogeneous catalyst) and sodium ascorbate in EtOH/H 2 O under microwave conditions at 100 °C for 5 min (Scheme ).…”

Section: Cuaac Click Chemistry Mediated Synthesis Of Diverse Glycocon...mentioning

confidence: 99%

“…The synthesis was achieved by clicking dipropargyl ether ( 208 , 1.0 equiv) to methyl 3-azidolithocholate ( 209 , 2.0 equiv) using Cu–Al mixed oxide (as heterogeneous catalyst) and sodium ascorbate in EtOH/H 2 O under microwave conditions at 100 °C for 5 min (Scheme ). The regioselective CuAAC method was chosen because of its ease of use and low cost.…”

Section: Cuaac Click Chemistry Mediated Synthesis Of Diverse Glycocon...mentioning

confidence: 99%

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Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

et al. 2021

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Copper(I)-catalyzed 1,3-dipolar cycloaddition between organic azides and terminal alkynes, commonly known as CuAAC or click chemistry, has been identified as one of the most successful, versatile, reliable, and modular strategies for the rapid and regioselective construction of 1,4-disubstituted 1,2,3-triazoles as diversely functionalized molecules. Carbohydrates, an integral part of living cells, have several fascinating features, including their structural diversity, biocompatibility, bioavailability, hydrophilicity, and superior ADME properties with minimal toxicity, which support increased demand to explore them as versatile scaffolds for easy access to diverse glycohybrids and well-defined glycoconjugates for complete chemical, biochemical, and pharmacological investigations. This review highlights the successful development of CuAAC or click chemistry in emerging areas of glycoscience, including the synthesis of triazole appended carbohydrate-containing molecular architectures (mainly glycohybrids, glycoconjugates, glycopolymers, glycopeptides, glycoproteins, glycolipids, glycoclusters, and glycodendrimers through regioselective triazole forming modular and bio-orthogonal coupling protocols). It discusses the widespread applications of these glycoproducts as enzyme inhibitors in drug discovery and development, sensing, gelation, chelation, glycosylation, and catalysis. This review also covers the impact of click chemistry and provides future perspectives on its role in various emerging disciplines of science and technology.

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Section: Cuaac Click Chemistry Mediated Synthesis Of Diverse Glycocon...mentioning

confidence: 99%

Section: Cuaac Click Chemistry Mediated Synthesis Of Diverse Glycocon...mentioning

confidence: 99%

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

et al. 2021

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“…In 2018, Negron-Silva et al 40 reported an efficient synthesis of a novel carbohydrate-lithocholic acid conjugate linked through 1,2,3-triazole rings and their derivatives.…”

Section: Synthesis Of Steroids Using the Cuaac "Click" Reactionmentioning

confidence: 99%

Recent syntheses of steroid derivatives using the CuAAC “click” reaction

Ibrahim‐Ouali¹,

Dumur²

2021

Arkivoc

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The introduction of heterocycles into steroids is often at the origin of a modification of their physiological activity and thus allows the formation of new biologically interesting molecules. Recent advances in the field of steroid synthesis using the copper-catalyzed azide-alkyne cycloaddition (CuAAC) are presented here. Compounds exhibiting known biological activities are also reported in this review. This approach holds great promise and allows us to consider preparing new, highly functionalized complex molecules using the CuAAC "click" reaction.

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“…Recently, we discovered that Cu-Al mixed oxide, generated by calcination of corresponding hydrotalcite type layered double hydroxide (LDH), in the presence of sodium ascorbate (NaAsc) as a reducing agent, efficiently catalyses the 1,3-dipolar cycloaddition of in situ-generated benzyl azides and phenyl acetylene in short reaction times using EtOH/H 2 O as a solvent [26]. In continuation with our interest in the synthesis of functional triazole derivatives [27][28][29][30], and in order to introduce the use of mixed oxides in carbohydrate CuAAC click chemistry, herein we report a rapid and facile synthesis of a series of carbohydrate-linked 1,2,3-triazole derivatives using as key step a three-component 1,3-dipolar azide-alkyne cycloaddition catalysed by Cu-Al mixed oxide, and an insight into their antimicrobial properties.…”

Section: Introductionmentioning

confidence: 98%

Cu–Al mixed oxide-catalysed multi-component synthesis of gluco- and allofuranose-linked 1,2,3-triazole derivatives

et al. 2020

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A series of carbohydrate-linked 1,2,3-triazole derivatives were synthesized in good yields from glucofuranose and allofuranose diacetonides using as key step a three-component 1,3-dipolar azide–alkyne cycloaddition catalysed by a Cu–Al mixed oxide. In this multi-component reaction, Cu–Al mixed oxide/sodium ascorbate system serves as a highly reactive, recyclable and efficient heterogeneous catalyst for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles. The reported protocol has significant advantages over classical CuI/ N , N -diisopropylethylamine (DIPEA) or CuSO 4 /sodium ascorbate conditions in terms of efficiency and reduced synthetic complexity. In addition, the selective deprotection of synthesized di- O -isopropylidene derivatives was also carried out leading to the corresponding mono- O -isopropylidene products in moderate yields. Some of the synthesized triazole glycoconjugates were tested for their in vitro antimicrobial activity using the disc diffusion method against Gram-positive bacteria ( Staphylococcus aureus and Bacillus subtilis ), Gram-negative bacteria ( Escherichia coli and Pseudomonas aeruginosa ), as well as fungus ( Aspergillus niger ) and yeast ( Candida utilis ). The results revealed that these compounds exhibit moderate to good antimicrobial activity mainly against Gram-negative bacteria.

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Design and synthesis of new carbohydrate-lithocholic acid conjugates linked via 1,2,3-triazole rings

Cited by 5 publications

References 47 publications

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

Recent syntheses of steroid derivatives using the CuAAC “click” reaction

Cu–Al mixed oxide-catalysed multi-component synthesis of gluco- and allofuranose-linked 1,2,3-triazole derivatives

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