Synthesis of a novel resorcin[4]arene–glucose conjugate and its catalysis of the CuAAC reaction for the synthesis of 1,4-disubstituted 1,2,3-triazoles in water

Husain, Ali; Bisht, Kirpal S.

doi:10.1039/c9ra00972h

Cited by 20 publications

(18 citation statements)

References 53 publications

(34 reference statements)

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“…This was followed by a glycosylation reaction to form compound 2 [39,40]. This compound was then treated with NaN 3 to obtain the desires azide intermediate 3 as white solid [41]. Similar procedure was followed for the synthesis of other glucose azide with three carbon spacer and galactose azides with 2 and 3 carbon spacers [42][43][44][45].…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Self-Assembling Properties of Peracetylated β-1-Triazolyl Alkyl D-Glucosides and D-Galactosides

et al. 2021

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Carbohydrate-based low-molecular-weight gelators (LMWGs) are useful classes of compounds due to their numerous applications. Among sugar-based LMWGs, certain peracetylated sugar beta-triazole derivatives were found to be effective organogelators and showed interesting self-assembling properties. To further understand the structural influence towards molecular assemblies and obtain new functional materials with interesting properties, we designed and synthesized a library of tetraacetyl beta-1-triazolyl alkyl-D-glucosides and D-galactosides, in which a two or three carbon spacer is inserted between the anomeric position and the triazole moiety. A series of 16 glucose derivatives and 14 galactose derivatives were synthesized and analyzed. The self-assembling properties of these new triazole containing glycoconjugates in different solvents were analyzed. Several glucose derivatives were found to be effective LMWGs, with compound 7a forming gels in a variety of organic solvents as well as in the presence of metal ions in aqueous solutions. The organogels formed by several compounds were characterized using optical microscopy, atomic force microscopy (AFM) and UV-vis spectroscopy, etc. The co-gels formed by compound 7a with the Fmoc derivative 7i showed interesting fluorescence enhancement upon gelation. Several gelators were also characterized using powder X-ray diffraction and FT-IR spectroscopy. The potential applications of these sugar-based gelators for drug delivery and dye removal were also studied.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Self-Assembling Properties of Peracetylated β-1-Triazolyl Alkyl D-Glucosides and D-Galactosides

et al. 2021

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“…Husain and Bisht developed a click inspired triazole-linked resorcin[4]arene glycoconjugate (RG) 1748 by reacting propargylated resorcin[4]arene 1746 with glycosyl azide 1747 in the presence of CuI/DIPEA in refluxing chloroform for 12 h (Scheme ). Triazole appended glycodendrimer 1748 was subjected to removal of acetate group using 0.1 M of sodium methoxide in methanol to give water-soluble glycodendrimer 1749 . This compound contains eight β- d -glucopyranoside residues on the upper rim of resorcin[4]-arene and thus is endowed with an expanded pseudosaccharide cavity that renders an appropriate molecular vessel for water insoluble hydrophobic azide and alkyne as clickable partners in an aqueous environment.…”

Section: Cuaac Carbo-click In Sensing Gelation Chelation Glycosylatio...mentioning

confidence: 99%

“…The authors successfully explored the inverse phase transfer molecular host nature of the resultant RG to act as a potent CuAAC catalyst for the regioselective synthesis 1,4-disubstituted triazole by reacting azide and alkyne in water as a green media. The method has notable advantages, such as excellent regioselectivity, excellent yields (in many cases, the yields were almost quantitative), and shorter reaction time under environmentally benign conditions, providing the additional merit for click-to-click catalysis …”

Section: Cuaac Carbo-click In Sensing Gelation Chelation Glycosylatio...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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“…In particular, triazole‐containing calixarene hybrids demonstrate sensor properties towards transition metal cations (Hg, Ag, Cu, Zn, Al) and neutral molecules and exhibit inhibitory and antitumor activities . Related resorcinarenes are equally interesting; they have been used to prepare triazole derivatives retaining the flexibility of the macrocycle and rigid cage systems exhibiting extraction, catalytic, fluorescence, and chromophore activities. It is noteworthy that available literature mainly addresses resorcinarenes with rccc configurations of lower‐rim substituents and with functionalized benzene rings being arranged on one side of the macrocycle, and only two publications deals with rctt resorcinarenes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Triazole‐Containing rctt Tetra‐C‐Naphthyl‐Calix [4]resorcinarene and 1,1‐Dinaphthylmethane Derivatives

et al. 2020

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rctt-Octatriazolyl-ortho-methyl-tetra-C-naphthyl-calix[4]resorcinarenes containing triazole moieties on the horizontally and vertically arranged benzene rings of the macrocyclic core; rctt tetra-triazolyl-tetra-phosphato-ortho-methyl-tetra-C-naphthylcalix[4]resorcinarene with triazole groups being bound only to the vertically arranged benzene rings of the macrocycle and the phosphate groups being immobilized on the horizontally arranged benzene rings; di-and tetra-triazolyl-dinaphthylmethanes differing in the number and spatial orientation of chelate pairs; and 2,2'-diphosphonato-dinaphthylmethanes in which exocyclic substituents include the phosphonate and the terminal triazole moieties connected by linkers differing in the steric crowding were synthesized, isolated in high yields, and characterized. In all cases, the catalytic azide-alkyne cycloaddition click reaction was the key step of the synthesis. One octatriazole calix[4]resorcinarene derivative was subjected to subsequent transformations in which the terminal ester groups in the triazole rings were converted to carboxyl and amide groups. The alkylation of rctt resorcinarenes with propargyl bromide and modification of octatriazole resorcinarene derivative with terminal ester groups by biologically active phenethylamine proceeded efficiently only under microwave irradiation.

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Synthesis of a novel resorcin[4]arene–glucose conjugate and its catalysis of the CuAAC reaction for the synthesis of 1,4-disubstituted 1,2,3-triazoles in water

Abstract: The Cu(i)-catalyzed azide–alkyne cycloaddition (CuAAC) in aqueous media using resorcin[4]arene glycoconjugate (RG) is reported.

Cited by 20 publications

References 53 publications

Synthesis and Self-Assembling Properties of Peracetylated β-1-Triazolyl Alkyl D-Glucosides and D-Galactosides

Synthesis and Self-Assembling Properties of Peracetylated β-1-Triazolyl Alkyl D-Glucosides and D-Galactosides

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

Synthesis of Triazole‐Containing rctt Tetra‐C‐Naphthyl‐Calix [4]resorcinarene and 1,1‐Dinaphthylmethane Derivatives

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