Top Buy Now Summary References
Home
>
Section
>
Chapter

Green synthesis of triazolo-nucleoside conjugates via azide-alkyne C-N bond formation

Kumar, R.; Maity, J.; Mathur, D.; Verma, A.; Rana, N.; Kumar, M.; Kumar, S.; Prasad, A.K.

Green-Bond Forming Reactions Carbon-Carbon and Carbon-Heteroatom: 61-104

2022

ISSN/ISBN: 9783110759549
Accession: 096607444

Full-Text Article emailed within 1 workday
Payments are secure & encrypted
Powered by Stripe
Powered by PayPal

Summary
Modified nucleosides are the core precursors for the synthesis of artificial nucleic acids, and are important in the field of synthetic and medicinal chemistry. In order to synthesize various triazolo-compounds, copper and ruthenium catalysed azide-alkyne 1,3-dipolar cycloaddition reactions also known as click reaction have emerged as a facile and efficient tool due to its simplicity and convenient conditions. Introduction of a triazole ring in nucleosides enhances their therapeutic value and various photophysical properties. This review primarily focuses on the plethora of synthetic methodologies being employed to synthesize sugar modified triazolyl nucleosides, their therapeutic importance and various other applications.

References

R.S., Kumar, Rajesh, S.; J., Maity, Jyotirmoy; D., Mathur, Divya; A., Verma, Abhishek; N., Rana, Neha; M.R., Kumar, Manish, R.; K.V., Sandeep, Kumar Vijay; A.K., Prasad, Ashok Kumar 2023: Green synthesis of triazolo-nucleoside conjugates via azide-alkyne C-N bond formation Physical Sciences Reviews 8(9): 2775-2818
Seela, F.; Sirivolu, V.R.; Chittepu, P. 2008: Modification of DNA with octadiynyl side chains: synthesis, base pairing, and formation of fluorescent coumarin dye conjugates of four nucleobases by the alkyne--azide "click" reaction Bioconjugate Chemistry 19(1): 211-224
Broggi, J.; Kumamoto, H.; Berteinaraboin, S.; Nolan, S.P.; Agrofoglio, L.A. 2009: Click Azide-Alkyne Cycloaddition for the Synthesis of D-(-)-1,4-Disubstituted Triazolo-Carbanucleosides European Journal of Organic Chemistry (12): 1880-1888
Akritopoulou-Zanze, I.; Gracias, V.; Djuric, S.W. 2004: A versatile synthesis of fused triazolo derivatives by sequential Ugi/alkyne-azide cycloaddition reactions Tetrahedron Letters 45(46): 8439-8441
Yan, Y.; Li, H.; Zhang, M.; Wang, R.; Zhou, C.; Ren, Z.; Ding, M. 2019: One-Pot Synthesis of [1,2,3]Triazolo[1,5-a]quinoxalin-4(5H)-ones by a Metal-Free Sequential Ugi-4CR/Alkyne–Azide Cycloaddition Reaction Synlett 31(01): 73-76
Cheshev, P.; Marra, A.; Dondoni, A. 2006: First synthesis of 1,2,3-triazolo-linked (1,6)-alpha-D-oligomannoses (triazolomannoses) by iterative Cu(I)-catalyzed alkyne-azide cycloaddition Organic and Biomolecular Chemistry 4(17): 3225-3227
Gracias, V.; Darczak, D.; Gasiecki, A.F.; Djuric, S.W. 2005: Synthesis of fused triazolo-imidazole derivatives by sequential van Leusen/alkyne–azide cycloaddition reactions Tetrahedron Letters 46(52): 9053-9056
R.N., Yadav, Ram Naresh; S., Chandra, Sunena; A., Paniagua, Armando; M.F., Hossain, Md Firoj; B.K., Banik, Bimal Krishna 2020: An Expeditious Route for the Synthesis of Oxazepine Triazolo-β-Lactams through Intramolecular Metal-Free [3 + 2] Azide-Alkyne Cycloaddition Australian Journal of Chemistry 73(7): 654-657
Agócs, A.; Bokor, .; Takátsy, A.; Lóránd, T.; Deli, J.; Somsák, L.; Nagy, V. 2017: Synthesis of carotenoid-monosaccharide conjugates via azide–alkyne click-reaction Tetrahedron 73(5): 519-526
Mathur, D.; Rana, N.; Olsen, C.E.; Parmar, V.S.; Prasad, A.K. 2014: Cu(I)-Catalyzed Efficient Synthesis of 2′-Triazolo-nucleoside Conjugates Journal of Heterocyclic Chemistry 52(3): 701-710
Singh, A.; Viljoen, A.; Kremer, L.; Kumar, V. 2017: Azide-alkyne cycloaddition en route to 4-aminoquinoline-ferrocenylchalcone conjugates: synthesis and anti-TB evaluation Future Medicinal Chemistry 9(15): 1701-1708
Gbadegesin, O.D.; Adesina, S.K. 2025: Synthesis and Characterization of Polymer-Drug Conjugates by Strain-Promoted Azide-Alkyne Cycloaddition-Mediated Polymerization Journal of Applied Polymer Science 142(21)
Avrutina, O.; Empting, M.; Fabritz, S.; Daneschdar, M.; Frauendorf, H.; Diederichsen, U.; Kolmar, H. 2009: Application of copper(I) catalyzed azide-alkyne [3+2] cycloaddition to the synthesis of template-assembled multivalent peptide conjugates Organic and Biomolecular Chemistry 7(20): 4177-4185
Sekine, T.; Takashima, Y.; Harada, A. 2015: Direct covalent bond formation between materials using copper(i)-catalyzed azide alkyne cycloaddition reactions RSC Advances 5(69): 56130-56135
Xu, Z.; Song, X.-F.; Hu, Y.-Q.; Qiang, M.; Lv, Z.-S. 2017: Azide-alkyne cycloaddition towards 1H-1,2,3-triazole-tethered gatifloxacin and isatin conjugates: Design, synthesis and in vitro anti-mycobacterial evaluation European Journal of Medicinal Chemistry 138: 66-71
Sharma, R.; Kumar, A. 2022: An expeditious and clean synthesis of novel benzotriazole-triazole conjugates via Copper-catalyzed Azide-Alkyne cycloaddition click protocol (CuAAC) Journal of Chemical Sciences 134(3): 69
Kavoosi, S.; Rayala, R.; Walsh, B.; Barrios, M.; Gonzalez, W.G.; Miksovska, J.; Mathivathanan, L.; Raptis, R.G.; Wnuk, S.F. 2016: Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide-alkyne click reactions and direct C-H bond functionalization Tetrahedron Letters 57(39): 4364-4367
Frank Seela; Xin Ming 2008: Oligonucleotides Containing 7-Deaza-2-deoxyinosine as Universal Nucleoside: Synthesis of 7-Halogenated and 7-Alkynylated Derivatives, Ambiguous Base Pairing, and Dye Functionalization by the Alkyne Azide Click Reaction Helvetica Chimica Acta 91(7): 1181-1200
Seela, F.; Xiong, H.; Leonard, P.; Budow, S. 2009: 8-Aza-7-deazaguanine nucleosides and oligonucleotides with octadiynyl side chains: synthesis, functionalization by the azide-alkyne 'click' reaction and nucleobase specific fluorescence quenching of coumarin dye conjugates Organic and Biomolecular Chemistry 7(7): 1374-1387
Su, Y.-C.; Lo, Y.-L.; Hwang, C.-C.; Wang, L.-F.; Wu, M.H.; Wang, E.-C.; Wang, Y.-M.; Wang, T.-P. 2014: Azide-alkyne cycloaddition for universal post-synthetic modifications of nucleic acids and effective synthesis of bioactive nucleic acid conjugates Organic and Biomolecular Chemistry 12(34): 6624-6633