A novel domino-click approach for the synthesis of sugar based unsymmetrical bis-1,2,3-triazoles

Arora, Bhupinder Singh; Shafi, Syed; Singh, Swarn; Ismail, Tabasum; Kumar, Halmuthur M. Sampath

doi:10.1016/j.carres.2007.10.021

Cited by 14 publications

(6 citation statements)

References 19 publications

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“…Also, a series of biologically significant unsymmetrical bis(1,2,3triazole)s were achieved by extending the protocol via a consecutive domino click reaction. 231 The Dondoni group successfully attempted to introduce an azido group at the C-40 position of rapamycin, which was further used to synthesize a library of triazole-bridged rapamycin glycoconjugates (86a−l) by CuAAC reaction of the resulting azidorapamycin (85) with several propargylated O-and Sglycosides as well a C-ethynyl derivative (Scheme 30). 232 Bera and co-workers used Cu-catalyzed click coupling for the synthesis of several disaccharide to oligosaccharide molecules with potential applications in chemical biology.…”

Section: Chemical Reviewsmentioning

confidence: 99%

“… The method excludes the necessity of solvents, ligands, and bases, and thus would be interesting for pharmaceutical and industrial research. Also, a series of biologically significant unsymmetrical bis(1,2,3-triazole)s were achieved by extending the protocol via a consecutive domino click reaction …”

Section: Click-chemistry-inspired Synthesis Of Diverse Triazolyl Glyc...mentioning

confidence: 99%

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Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), popularly known as the "click reaction", serves as the most potent and highly dependable tool for facile construction of simple to complex architectures at the molecular level. Click-knitted threads of two exclusively different molecular entities have created some really interesting structures for more than 15 years with a broad spectrum of applicability, including in the fascinating fields of synthetic chemistry, medicinal science, biochemistry, pharmacology, material science, and catalysis. The unique properties of the carbohydrate moiety and the advantages of highly chemo- and regioselective click chemistry, such as mild reaction conditions, efficient performance with a wide range of solvents, and compatibility with different functionalities, together produce miraculous neoglycoconjugates and neoglycopolymers with various synthetic, biological, and pharmaceutical applications. In this review we highlight the successful advancement of Cu(I)-catalyzed click chemistry in glycoscience and its applications as well as future scope in different streams of applied sciences.

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Section: Chemical Reviewsmentioning

confidence: 99%

Section: Click-chemistry-inspired Synthesis Of Diverse Triazolyl Glyc...mentioning

confidence: 99%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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“… The approach excludes the requirements for ligands, solvents, and bases and, therefore, would be suitable to scale-up. Also, a library of biologically significant asymmetrical bis-1,2,3-triazoles was produced extending the devised protocol via a successive domino-click reaction …”

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

confidence: 87%

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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“…They are used as intermediates in antibiotic synthesis [7], antihistamine preparations [8], and chemiluminescent compounds [9]. They also exhibit inhibitory activity against tuberculosis mycobacteria [10] and HIV-1 protease [11].…”

Section: Introductionmentioning

confidence: 99%