Synthesis of fluorescent coumarin triazolylglycosides

Nyuchev, Alexander V.; Sharonova, E. A.; Len’shina, N. A.; Shavyrin, A. S.; Lopatin, M. A.; Balalaeva, Irina V.; Beletskaya, I. P.; Fedorov, Alexey Yu.

doi:10.1016/j.tetlet.2011.06.016

Cited by 19 publications

(9 citation statements)

References 45 publications

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“…Thus, the Suzuki-Miyaura [36][37][38][39][40][41][42][43][44][45], Stille [37], Negishi [46], Sonogashira [47][48][49], Heck [50,51], and Buchwald-Hartwig [52][53][54] reactions are used to obtain various aryl-, hetaryl-, alkenyl-, alkynyl-, and also N-hetaryl-and amino-containing coumarins in high yield. [Pd]-cat.…”

Section: Functionalization and Modification Of The Coumarin Skeletonmentioning

confidence: 99%

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Catalytic methods of creation and functionalization of the coumarin skeleton

Fedorov

Nyuchev

Beletskaya

2012

Chem Heterocycl Comp

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Section: Functionalization and Modification Of The Coumarin Skeletonmentioning

confidence: 99%

“…It should be mentioned that ethynyl coumarins are also capable of interacting effectively with organic azides in the presence of copper salts [67].…”

Section: Functionalization and Modification Of The Coumarin Skeletonmentioning

confidence: 99%

Catalytic methods of creation and functionalization of the coumarin skeleton

Fedorov

Nyuchev

Beletskaya

2012

Chem Heterocycl Comp

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“…No doubt, a number of standard protocols are known to incorporate terminal alkyne groups in a broad range of scaffolds, particularly heterocycles, arenes, amino acids, etc. Widely explored necessary methods for easy access to terminal alkynes include the Sonogashira coupling, which is the coupling of TMS-alkyne with halogen, trifluoromethansulfonate or other good leaving groups on the alkene of a 1,3-conjugated system under Pd catalysis …”

Section: Carbohydrate-based Azides and Alkynes: Beneficial Partners F...mentioning

confidence: 99%

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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“…Luminescence for surface imaging (Nyuchev et al, 2011) Decaprenylphosphorylarabinose analogues TOF (DHB) As arabinofuranosyl donors with mycobacterial arabinosyltransferase 1,2-Diamino-4,5-methylenedioxybenzenelabeled trimer of 2,8-linked sialic acid…”

Section: Synthetic Glycosides and Related Compoundsmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

Harvey

2015

Mass Spectrometry Reviews

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This review is the seventh update of the original article published in 1999 on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2012. General aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, and fragmentation are covered in the first part of the review and applications to various structural types constitute the remainder. The main groups of compound are oligo- and poly-saccharides, glycoproteins, glycolipids, glycosides, and biopharmaceuticals. Much of this material is presented in tabular form. Also discussed are medical and industrial applications of the technique, studies of enzyme reactions, and applications to chemical synthesis. © 2015 Wiley Periodicals, Inc. Mass Spec Rev 36:255-422, 2017.

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Synthesis of fluorescent coumarin triazolylglycosides

Cited by 19 publications

References 45 publications

Catalytic methods of creation and functionalization of the coumarin skeleton

Catalytic methods of creation and functionalization of the coumarin skeleton

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

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

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