Synthesis and Photophysical Studies on N1-(2′-O,4′-C-Methyleneribofurano-nucleoside-3′-yl)-C4-(coumarin-7-oxymethyl)-1,2,3-triazoles

Srivastava, Smriti; Maikhuri, Vipin K.; Kumar, Rajesh; Bohra, Kapil; Singla, Harbansh; Maity, Jyotirmoy; Prasad, Ashok K.

doi:10.1016/j.carres.2018.09.007

Cited by 8 publications

(12 citation statements)

References 33 publications

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“…Thus, the newly synthesized coumarintriazolylmethyl nucleoside conjugates were found to show better Stokes Shift values in comparison to coumarin-triazolyl bicyclonucleoside conjugates. [23] These newly synthesized coumarin-triazolylmethyl nucleoside conjugates 8 a-f, 9 a-f having high Stokes shift values can be conjugated to oligonucleotides for producing fluorescent oligonucleotides that can be used as extremely sensitive hybridization probes for DNA microarray and PCR analyses. Quantum yields calculated for 8 a-c, 9 a-c were found in the range of 0.02-0.06 while for 8 d-f, 9 d-f in range of 0.20-0.36.…”

Section: Resultsmentioning

confidence: 99%

“…The photophysical studies of the synthesised compounds 8 a-f, 9 a-f revealed that they possess high fluorescence properties and on comparison of Stokes shift value, it was observed that they showed better Stokes shift value compared to the known coumarin-triazolylmethyl bicyclic-nucleosides. [23] This may be attributed to the more flexibility of the furanose ring of the sugar moiety of the synthesized conjugates with respect to the flexibility of bicyclic sugar moiety of earlier compounds.…”

Section: Discussionmentioning

confidence: 99%

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Synthesis and Photophysical Studies on N¹‐(Coumarin‐4′′′‐yl)‐C⁴‐(2′,3′‐dideoxyuridin‐3′‐yl/3′‐deoxythymidin‐3′‐yl)‐oxymethyl‐1,2,3‐triazoles

et al. 2023

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A click chemistry‐based protocol has been utilized for the synthesis of a series of twelve novel tert‐butyldiphenylsilylated N1‐(coumarin‐4′′′‐yl)‐C4‐(2′,3′‐di‐deoxyuridin‐3′‐yl)‐oxymethyl‐1,2,3‐triazoles and N1‐(coumarin‐4′′′‐yl)‐C4‐(3′‐deoxythymin‐3′‐yl)‐oxymethyl‐1,2,3‐triazoles by utilising Cu(I)‐catalyzed azide‐alkyne cycloaddition reaction of 4‐azidocoumarins and 3′‐O‐(prop‐1‐yn‐3‐yl)‐5′‐O‐(tert‐butyldiphenylsilyl)‐2′,3′‐dideoxyuridin or 3′‐O‐(prop‐1‐yn‐3‐yl)‐5′‐O‐(tert‐butyldiphenylsilyl)‐3′‐deoxythymidin in 70–82 % and 68–82 % yields, respectively. The deprotection of resulted silylated uridine and thymidine conjugate with TBAF afforded title compounds in 81–91 % yield. The photophysical studies have been carried out on the synthesized coumarin‐triazolylmethyl nucleoside conjugates which revealed a very high Stokes shift value ranging from 82–215 nm.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Synthesis and Photophysical Studies on N¹‐(Coumarin‐4′′′‐yl)‐C⁴‐(2′,3′‐dideoxyuridin‐3′‐yl/3′‐deoxythymidin‐3′‐yl)‐oxymethyl‐1,2,3‐triazoles

et al. 2023

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“…Likewise, modified nucleosides linked via CuAAC-mediated triazole with other related systems, including coumarin and carbohydrates were further explored. , The coumarin scaffold is known to display a broad range of pharmacological activities and photophysical properties. Consequently, the triazole skeleton linked to a coumarin residue could bring remarkable improvement in biological and photophysical properties.…”

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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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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“…24 The appearance of the proton in coumarins at 7.06-7.88 ppm further proved the successful nucleophilic substitution between hydroxyl in coumarins and C-6-Br in chitosan. 25,26…”

Section: Chemical Synthesis and Characterizationmentioning

confidence: 99%

Significantly enhanced antioxidant activity of chitosan through chemical modification with coumarins

Wei

Zhang

et al. 2019

Polym. Chem.

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Synthesis and Photophysical Studies on N1-(2′-O,4′-C-Methyleneribofurano-nucleoside-3′-yl)-C4-(coumarin-7-oxymethyl)-1,2,3-triazoles

Cited by 8 publications

References 33 publications

Synthesis and Photophysical Studies on N¹‐(Coumarin‐4′′′‐yl)‐C⁴‐(2′,3′‐dideoxyuridin‐3′‐yl/3′‐deoxythymidin‐3′‐yl)‐oxymethyl‐1,2,3‐triazoles

Synthesis and Photophysical Studies on N¹‐(Coumarin‐4′′′‐yl)‐C⁴‐(2′,3′‐dideoxyuridin‐3′‐yl/3′‐deoxythymidin‐3′‐yl)‐oxymethyl‐1,2,3‐triazoles

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

Significantly enhanced antioxidant activity of chitosan through chemical modification with coumarins

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Synthesis and Photophysical Studies on N1-(2′-O,4′-C-Methyleneribofurano-nucleoside-3′-yl)-C4-(coumarin-7-oxymethyl)-1,2,3-triazoles

Cited by 8 publications

References 33 publications

Synthesis and Photophysical Studies on N1‐(Coumarin‐4′′′‐yl)‐C4‐(2′,3′‐dideoxyuridin‐3′‐yl/3′‐deoxythymidin‐3′‐yl)‐oxymethyl‐1,2,3‐triazoles

Synthesis and Photophysical Studies on N1‐(Coumarin‐4′′′‐yl)‐C4‐(2′,3′‐dideoxyuridin‐3′‐yl/3′‐deoxythymidin‐3′‐yl)‐oxymethyl‐1,2,3‐triazoles

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

Significantly enhanced antioxidant activity of chitosan through chemical modification with coumarins

Contact Info

Product

Resources

About

Synthesis and Photophysical Studies on N¹‐(Coumarin‐4′′′‐yl)‐C⁴‐(2′,3′‐dideoxyuridin‐3′‐yl/3′‐deoxythymidin‐3′‐yl)‐oxymethyl‐1,2,3‐triazoles

Synthesis and Photophysical Studies on N¹‐(Coumarin‐4′′′‐yl)‐C⁴‐(2′,3′‐dideoxyuridin‐3′‐yl/3′‐deoxythymidin‐3′‐yl)‐oxymethyl‐1,2,3‐triazoles