Click Inspired Synthesis of 1,2,3‐Triazole‐linked 1,3,4‐Oxadiazole Glycoconjugates

Kushwaha, Divya; Tiwari, Vinod K.

doi:10.1002/jhet.2845

Cited by 6 publications

(12 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These isomers were differentiated on the basis of their 1 H and 13 C NMR. In H NMR spectra of α-derivative 2f the anomeric proton appeared at δ 5.16 ppm as singlet whereas, the anomeric proton of β-isomer 2g appeared at δ 4.99 ppm as doublet which was confirmed through literature 30 . Also, in 13 C NMR spectra of α-isomer 2f, the anomeric carbon peak appeared at 104.8 ppm whereas, for β-isomer 2g, it appeared at 100.4 ppm.…”

Section: Resultssupporting

confidence: 60%

“…3-O-Propargylation of acetonide protected glucose using propargyl bromide in THF in presence of NaH at room temperature for 10 hours afforded respective 3-O-propargyl ether derivative 2a according to the procedure described in literature (Fig. 3) 30 . Treatment of compound 2a with 70% aqueous acetic acid resulted into selective deprotection of isopropylidine group to furnish diol derivative 2b 30 .…”

Section: Resultsmentioning

confidence: 99%

“…3) 30 . Treatment of compound 2a with 70% aqueous acetic acid resulted into selective deprotection of isopropylidine group to furnish diol derivative 2b 30 . Another modification was done in diol 2b by reaction with sodium metaperiodate in presence of NaHCO 3 followed by reduction with sodium borohydride to afford derivative 2c (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Another modification was done in diol 2b by reaction with sodium metaperiodate in presence of NaHCO 3 followed by reduction with sodium borohydride to afford derivative 2c (Fig. 3) 30 .…”

Section: Resultsmentioning

confidence: 99%

“…Also, in 13 C NMR spectra of α-isomer 2f, the anomeric carbon peak appeared at 104.8 ppm whereas, for β-isomer 2g, it appeared at 100.4 ppm. O-Propargyl ether derivative 2f was subjected to selective deprotection by treatment with 50% acetic acid-water to afford diol derivative 2,3-O-isopropylidine-1-O-propargyl-β-D-mannofuranose 2h 30 . The selective oxidation of compound 2h with sodium metaperiodate in presence of sodium bicarbonate afforded respective aldehyde derivative which at the end on reduction with sodium borohydride afforded respective propargylated mannose derivative 2i 30 (Fig.…”

Section: Resultsmentioning

confidence: 99%

See 4 more Smart Citations

Click Inspired Synthesis of Novel Cinchonidine Glycoconjugates as Promising Plasmepsin Inhibitors

Mishra

Agrahari

Bose

et al. 2020

Sci Rep

Self Cite

View full text Add to dashboard Cite

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...

show abstract

Section: Resultssupporting

confidence: 60%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…Another modification was done in diol 2b by reaction with sodium metaperiodate in presence of NaHCO 3 followed by reduction with sodium borohydride to afford derivative 2c (Fig. 3) 30 .…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 3 more Smart Citations

Click Inspired Synthesis of Novel Cinchonidine Glycoconjugates as Promising Plasmepsin Inhibitors

Mishra

Agrahari

Bose

et al. 2020

Sci Rep

Self Cite

View full text Add to dashboard Cite

show abstract

Design, Synthesis, and Docking Study of Quinine‐9‐Triazolyl Conjugates

Tiwari

Bose

Singh

et al. 2023

Chemistry & Biodiversity

Self Cite

View full text Add to dashboard Cite

To develop a better chemotherapeutically potential candidate for lung cancer treatment and cure with repurposed motifs, quinine has been linked with biocompatible CuAAC‐inspired regioselective 1,2,3‐triazole linker and a series of ten novel 1,2,3‐triazolyl‐9‐quinine conjugates have been developed by utilizing click conjugation of glycosyl ether alkynes with 9‐epi‐9‐azido‐9‐deoxy‐quinine under standard click conditions. In parallel, the docking study indicated that the resulting conjugates have an overall appreciable interaction with ALK‐5 macromolecules. Moreover, the mannose‐triazolyl conjugate exhibited the highest binding interactions of −7.6 kcal/mol with H‐bond interaction with the targeted macromolecular system and indicate the hope for future trials for anti‐lung cancer candidates.

show abstract

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

et al. 2021

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Click Inspired Synthesis of 1,2,3‐Triazole‐linked 1,3,4‐Oxadiazole Glycoconjugates

Cited by 6 publications

References 48 publications

Click Inspired Synthesis of Novel Cinchonidine Glycoconjugates as Promising Plasmepsin Inhibitors

Click Inspired Synthesis of Novel Cinchonidine Glycoconjugates as Promising Plasmepsin Inhibitors

Design, Synthesis, and Docking Study of Quinine‐9‐Triazolyl Conjugates

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

Contact Info

Product

Resources

About