Synthesis of triazolylmethyl-linked nucleoside analogs via combination of azidofuranoses with propargylated nucleobases and study on their cytotoxicity

Halay, Erkan; Ay, Emriye; Şalva, Emine; Ay, Kadir; Karayıldırım, Tamer

doi:10.1007/s10593-018-2248-4

Cited by 14 publications

(12 citation statements)

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“…Ay and co-workers explored a series of triazolyl nucleoside glycohybrids as anticancer phramacophores, which were developed utilizing a CuAAC protocol through coupling of azido furanoses and propargylated nucleobases under standard catalytic conditions . The authors evaluated the anticancer activity of the resulting glycohybrids against MDA-MB-231, Hep3B, PC-3, SH-SY5Y, and HCT-116 cell lines, and a few analogues displayed promising cytotoxic activities.…”

Section: Application Of Carbo-cuaac Click Chemistry In Drug Discovery...mentioning

confidence: 83%

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: Application Of Carbo-cuaac Click Chemistry In Drug Discovery...mentioning

confidence: 83%

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

et al. 2021

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“…The regioselective synthesis of N-allyl and N-propargyl A and T, using commercially available allyl bromide 22 and propargyl bromide 27, has been described in the literature. [23,24,28,[48][49] In general, the products were obtained in low to high yields (25-89 %) typically using conventional heating overnight or for more than one day. The N-allylation of T was also described involving two reaction steps, first heating at 65°C for 30 min followed by MW irradiation for 2 min.…”

Section: Functionalization Of Nucleobases Via N-allylation and N-propargylation Reactionsmentioning

confidence: 99%

“…The N-propargylated nucleobases 23-26 were obtained following the procedures described elsewhere, [23,24,[48][49][50] with some modifications. The A, T and C were initially treated with NaH in dry DMF, followed by the addition of propargyl bromide 27 at r.t. to generate the products in modest to high yield (25-63 %) (Table 4).…”

Section: Functionalization Of Nucleobases Via N-allylation and N-propargylation Reactionsmentioning

confidence: 99%

Customizable and Regioselective One‐Pot N−H Functionalization of DNA Nucleobases to Create a Library of Nucleobase Derivatives for Biomedical Applications

et al. 2021

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DNA is one of the most exciting biomolecules in nature for developing supramolecular biofunctional nanoarchitectures owing to the highly specific and selective interactions between complementary Watson-Crick base pairing. Herein, simple and one-pot synthetic procedures have been implemented for producing a library of DNA nucleobase derivatives endowed with reactive functional groups for bioconjugation and crosslinking strategies with other (bio)molecules. Purine and pyrimidine molecules have been regioselectively NÀ H functionalized either via N-alkylation, N-allylation, N-propargylation or Michael-type reactions and structurally characterized. The influence of the reaction conditions was assessed and discussed. The in vitro biocompatibility of the native and nucleobase derivatives was evaluated by culturing them with human fibroblasts, revealing their cytocompatibility. The library of nucleobase derivatives holds great promise for being coupled to different biomolecules, including biopolymeric materials, lipids, and peptides, thus potentially leading to modular supramolecular nanobiomaterials for biomedicine.

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“…1,2,3-Triazoles are a noteworthy class of heterocyclic compounds that have attracted a great deal of attention from chemists due to their potential biological activities, such as antiviral, antimicrobial, antiallergic, and anti-HIV activities and their applications in anticonvulsants, dyes, corrosion inhibitors, sensors, and photo-stabilizers [17][18][19][20][21][22][23]. Only a few general methods for the synthesis of 1,2,3-triazoles have been described, i.e., a) Huisgen [3+2] 1,3-Dipolar Cycloaddition, b) Copper-Catalyzed Azide-Alkyne Cycloaddition (Cu-AAC) [20], c) Ruthenium-Catalyzed Azide-Alkyne Cycloaddition (RuAAC) [19], d) Dimroth reaction, as a cycloaddition of azides with active methylene compounds in the presence of basic conditions [24,25]. A highly efficient copper(I)-or rutheniumcatalyzed method for the chemo-and regioselective-synthesis of 1,2,3-triazoles from organic azides and alkynes is the most frequently used.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel 1,2,3-triazole-bridged oxime polyurethanes obtained from an isomannide derivative

Bayrak

Oral

2021

Maced. J. Chem. Chem. Eng.

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Polyurethanes (PUs) are synthesized by the reaction of diisocyanates and diols and are widely used in furniture foams, thermal insulation, coatings, and adhesives. In this work, a 1,2,3-triazole-bridged dioxime (compound 6) as a diol source was synthesized from isomannide via tosylation, azidation, and cyclization-addition and used in the syntheses of new PUs. A new carbohydrate-based linear P-1 was synthesized by the reaction of 6 and 1,6-hexamethylene diisocyanate (1,6-HMDI). Besides, three new linear PUs (P-2, P-3, and P-4) were synthesized by the reaction of 6, isomannide compound (used in different molar ratios), and 1,6-HMDI. The thermal properties of the new PUs were determined by thermogravimetry (TG), their molecular structures were characterized by FTIR, 1H- and 13C-NMR, and the molecular weights of some polymers were determined by GPC/SEC. Additionally, the surface characteristics of the synthesized PUs were examined via scanning electron microscopy (SEM).

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Synthesis of triazolylmethyl-linked nucleoside analogs via combination of azidofuranoses with propargylated nucleobases and study on their cytotoxicity

Cited by 14 publications

References 50 publications

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

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

Customizable and Regioselective One‐Pot N−H Functionalization of DNA Nucleobases to Create a Library of Nucleobase Derivatives for Biomedical Applications

Synthesis and characterization of novel 1,2,3-triazole-bridged oxime polyurethanes obtained from an isomannide derivative

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