Synthesis of Novel Bis-Triazolyl Glycoconjugates via Dual Click Reaction for the Selective Recognition of Cu(II) Ions

Mishra, Amrita; Tiwari, Vinod K.

doi:10.1002/slct.201702033

Cited by 8 publications

(9 citation statements)

References 41 publications

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“…[67] Likewise, bidentate 1 propargylated mannitol 99 was identified as a suitable sensor for the selective recognition of Cu 2 + ions. [68] as suggested by the Job plot, the probe 100 resulted for 1 : 1 complexation with Cu 2 + ions with detection limit of 8.00 μM.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 78%

“…On optimizing the reaction, K 2 CO 3 and ZnCl 2 gave the best results in presence of imidazole‐1‐sulphonyl azide, a diverse range of novel triazolyl glycoconjugates 98 were developed in high yields (Scheme 18). [67] Likewise, bidentate 1,4 : 3,6‐dianhydro‐D‐mannitol‐based bidentate glycohybrid 100 , obtained through CuAAC conjugation of azide 96 with di‐ O ‐propargylated mannitol 99 was identified as a suitable sensor for the selective recognition of Cu 2+ ions [68] . as suggested by the Job plot, the probe 100 resulted for 1 : 1 complexation with Cu 2+ ions with detection limit of 8.00 μM.…”

Section: Carbohydrate‐containing Molecules As New Chemical Entities (Nces)mentioning

confidence: 96%

“…Tandem synthesis of glycosyl-β-azidoesters 96 from olefinic ester 1 and its applications. [67,68] Thus, glycosyl alkyne 105 was first underwent CuAAC coupling with sugar azide as part of O-(2-or 3-azidomethylbenzyl)-protected glycosyl acceptors (106 and 109) and resulting triazole-linked disaccharides were subjected to pmethoxybenzyl group removal by treating the individual disaccharides with DDQ in DCM/H 2 O at rt for 2 h to furnish the required donor-acceptor systems (107 and 110), which were then subjected to intramolecular glycosylation (using NIS/TfOTMS in dry DCM) to furnish the desired disaccharide-containing triazole-linked macrocyclic systems (108 and 111) with good yield and also with an anticipated anomeric selectivities (Scheme 20). [72] In addition to the high natural abundance (led to easy availability and low cost), the spatial arrangement of multiple hydroxyl groups present in rigid sugar architecture (pyranose and furanose form) and moreover their straightforward transformation to a choice of functionalities, tender wide prospects to modify such glycohybrids into appropriate ligands in organic synthesis (Figure 6).…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

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Development of Diverse Range of Biologically Relevant Carbohydrate‐Containing Molecules: Twenty Years of Our Journey**

Tiwari

2021

The Chemical Record

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There is an increasing demand for significant amount of carbohydrate‐containing molecules owing to their complete chemical, biological, and pharmacological investigations to better understand their role in many important biological events. Clinical studies of a wide range of simple carbohydrates or their derivatives, glycohybrids, glycoconjugates, and neoglycoconjugates have been conducted worldwide for the successful treatment of various frontline diseases. Herein, a brief perspective of carbohydrate‐based molecular scaffolding and my experience during the last 20 years in the area of synthetic carbohydrate chemistry, mainly for their impact in drug discovery & development, is presented.

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Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 78%

Section: Carbohydrate‐containing Molecules As New Chemical Entities (Nces)mentioning

confidence: 96%

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

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Development of Diverse Range of Biologically Relevant Carbohydrate‐Containing Molecules: Twenty Years of Our Journey**

Tiwari

2021

The Chemical Record

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“… Similar CuAAC conjugation of azide 110a with di- O -propargylated ethers resulted in corresponding bis-triazolyl glycoconjugates having bidentate 3- O -protected α- d -glucofuranose with two triazole residues at appropriate positions of the carbohydrate scaffold. Supported by the ultraviolet spectrum, one of the analogues, 1,4:3,6-dianhydro- d -mannitol-based bidentate glycohybrid 174 , was obtained by reacting azide 110a with d -mannitol derived bisalkyne 173 , and bis-triazolyl glycoconjugate 174 was identified as a suitable sensor for the selective recognition of Cu 2+ ions . Interestingly, the probe 174 resulted in 1:1 complexation with Cu 2+ ions with a detection limit of 8.00 μM, as suggested by the Job plot.…”

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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“…Cu-Catalyzed click reaction is a facile and high yielding approach for 1,3-dipolar cycloaddition of organic azides and terminal alkynes which goes well with carbohydrate moiety and has produced very interesting glycosyl triazoles with various applications 14 . Thus, in continuation of our previous experience on click chemistry in glycoscience, [15][16][17][18][19][20][21][22][23][24][25][26][27] this reaction was chosen for cycloaddition reaction of cinchonidine-derived azide and sugar-derived terminal alkynes to achieve our designed target molecules (Fig. 1).…”

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confidence: 99%

Click Inspired Synthesis of Novel Cinchonidine Glycoconjugates as Promising Plasmepsin Inhibitors

Mishra

Agrahari

Bose

et al. 2020

Sci Rep

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Among all the malaria parasites, P. falciparum is the most predominant species which has developed drug resistance against most of the commercial anti-malarial drugs. Thus, finding a new molecule for the inhibition of enzymes of P. falciparum is the pharmacological challenge in present era. Herein, ten novel molecules have been designed with an amalgamation of cinchonidine, carbohydrate moiety and triazole ring by utilizing copper-catalyzed click reaction of cinchonidine-derived azide and clickable glycosyl alkynes. the molecular docking of developed molecules showed promising results for plasmepsin inhibition in the form of effective binding with target proteins. Malaria has been a medical challenge for centuries mostly in tropical and subtropical countries of the world. Despite significant medical advancement in treatment and prevention of malaria, it still causes thousands of deaths every year 1. The main cause of the disease is protozoan parasite Plasmodium which is generally transmitted by an infected female Anopheles mosquito. Out of five species of Plasmodium responsible for malaria in human, i.e. Plasmodium falciparum, Plasmodium vivax, Plasmodium knowlesi, Plasmodium malariae and Plasmodium ovale, Plasmodium falciparum is the most virulent and accounts most of the deaths caused by malaria. There are several anti-malarial drugs available in markets which act against malaria parasite with different modes of action, but due to rapid spread of drug resistance in malaria parasites mainly Plasmodium falciparum, the need of new antimalarial drug leads is increasing. Plasmepsins, enzymes produced by Plasmodium falciparum, play a key role in hemoglobin-degrading activity of the parasite by export of Plasmodium proteins to the host cell surface 2. Plasmepsin I and II are known to play crucial role in hemoglobin catabolism by cleaving the hemoglobin alpha chain between Phe33 and Leu34 which are located in hinge region which results into dislocation and partial unfolding of globin subunits which further causes more protease sites within the globin polypeptide chains. At this stage, further degradation of large globin fragments takes place by action of plasmepsins and falcipains. In this regards, plasmepsins, which play a key role in the survival of P. falciparum in the host, have emerged as the new effective targets for development of antimalarial drugs with plasmepsin inhibition mode of action. Because of their key functioning in malaria symptoms and consequences, these enzymes are the main target of the anti-malarial drugs 3,4. Recent researches related to anti-malarial drug development have focused plasmepsin inhibition largely 5-8. Thus, the molecules showing inhibitory activities against plasmepsin enzymes can come out to be promising drug leads for treatment of malaria. Cinchona alkaloids are cheap natural source of anti-malarial activity which provides opportunity towards development of new anti-malarial drug leads by synthetic modifications in their chemical structures. The anti-malarial activities of the fo...

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Synthesis of Novel Bis-Triazolyl Glycoconjugates via Dual Click Reaction for the Selective Recognition of Cu(II) Ions

Cited by 8 publications

References 41 publications

Development of Diverse Range of Biologically Relevant Carbohydrate‐Containing Molecules: Twenty Years of Our Journey**

Development of Diverse Range of Biologically Relevant Carbohydrate‐Containing Molecules: Twenty Years of Our Journey**

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

Click Inspired Synthesis of Novel Cinchonidine Glycoconjugates as Promising Plasmepsin Inhibitors

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