One‐Pot Facile Synthesis of 1,5‐Disubstituted Triazolyl Glycoconjugates from Nitrostyrenes

Mishra, Kunj B.; Tiwari, Vinod K.

doi:10.1002/slct.201600994

Cited by 18 publications

(23 citation statements)

References 34 publications

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“…1,3,4‐Oxadiazoles linked to sugar skeleton such as a glucofuranose, glucopyranose, xylopyranose, psicopyranose, thioglycosides and fructopyranose are documented in literature, and many of these derivatives have showed potential antibacterial, anticancer, antitumor, and antidiabetic activity . Considering the aforementioned facts and our previous experience on click‐mediated development of glycoconjugates of diverse application , we intend to conjugate the orthogonally protected saccharide residue with biologically privileged 1,3,4‐oxadiazole framework using Cu(I)‐catalyzed click reaction to obtain glycohybrids, which may exhibit the medicinal properties of both the parent components. Herein, we report a straightforward synthesis of 1,2,3‐triazole linked 1,3,4‐oxadiazole‐sugar derivatives by click reaction of an azide armed 1,3,4‐oxadiazole entity with diverse set of terminal glycosyl alkynes under mild reaction condition.…”

Section: Introductionmentioning

confidence: 99%

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

Kushwaha

Tiwari

2017

Journal of Heterocyclic Chem

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The glycoconjugation of biologically privileged 1,3,4‐oxadiazole scaffold is described via Cu(I)‐catalyzed azide–alkyne cycloaddition. A series of glycosyl alkynes 1b–i, obtained from various commercial sugars, were treated with azide functionalized 1,3,4‐oxadiazole using click chemistry to access triazole‐linked glycosylated 1,3,4‐oxadiazoles 10b–i in good yields. The structure of the developed glycoconjugates has been ascertained by extensive spectroscopic analysis (1H &13C NMR, IR, and MS).

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Section: Introductionmentioning

confidence: 99%

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

Kushwaha

Tiwari

2017

Journal of Heterocyclic Chem

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“…Synthesis of glycosyl alkyne 2d was again started from acetonide protected glucose, which on reaction with n-propyl bromide in presence of NaH followed by treatment with 50% aqueous acetic acid afforded respective diol derivative 31 . Resulted diol was subjected to oxidation with sodium metaperiodate in presence of NaHCO 3 followed by reduction in presence of sodium borohydride and at last the hydroxy derivative thus obtained on propargylation with propargyl bromide in presence of sodium hydride gave high yield of respective glucose derived O-propargyl derivative 2d (Fig.…”

Section: Resultsmentioning

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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“…To synthesize sulfonyl functionalized 1,4,5‐substituted triazolyl glycoconjugates, several carbohydrate‐derived azides ( 1a–v ) (Table.2, 3 & 4) were prepared by using the literature procedures . Having prepared these glycosyl azides, we initiated to optimize the yield of 5 a using several reaction conditions with various catalysts, solvent systems at different temperature.…”

Section: Resultsmentioning

confidence: 99%

“…Very recently, an enamine‐mediated amino acid or amine catalyzed [3+2] cycloaddition reaction of different carbonyl compounds (enones, β‐keto esters, ketones and enals) with aryl azides was reported by Ramachary, Bressy and Wang to furnish 1,4,5‐trisubstituted 1,2,3‐triazoles in good yields. More recently Tiwari and coworkers reported the p ‐TsOH prompted synthesis of 1,5‐disubstituted triazolyl glycoconjugates from nitrostyrenes.…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic [3+2] Cycloadditions: Toward Facile Synthesis of Sulfonyl-1,2,3-Triazolyl and Fully Substituted 1,2,3-Triazolyl Glycoconjugates

et al. 2017

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A general strategy was developed for the synthesis of Sulfonyl-1,2,3-triazolyl glycoconjugates (5a-n) and fully decorated 1,2,3triazolyl glycoconjugates (6a-w & 6 aa-6 ah) in the presence of catalytic amounts of organocatalyst. Ramachary-Bressy-Wang organocatalytic azide-ketone [3 + 2]-cycloaddition (OrgAKC) reaction of b-keto sulfones act as internal alkynes with glycosyl azides are reported for the synthesis of Sulfonyl-1,2,3-triazolyl glycoconjugates at 50 8C in good to excellent yields of products in the presence of catalytic amounts of pyrrolidine (10 mol %). In the similar way, Ramachary OrgAKC reaction of a variety of substituted phenyl ketones as internal alkynes with different glycosyl azides are reported for the synthesis of 1,2,3-triazolyl glycoconjugates at room temperature in good to excellent yields with high regioselectivity in the presence of catalytic amounts of DBU (10 mol %) using DMSO as solvent. The work mainly focuses on the application of this methodology to making glycoconjugates and establishes an alternative tool for the synthesis of fully decorated glyco-triazoles from the already known copper catalysed azide-alkyne [3 + 2] cycloaddition (CuAAC), RuAAC and IrAAC click reactions.

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One‐Pot Facile Synthesis of 1,5‐Disubstituted Triazolyl Glycoconjugates from Nitrostyrenes

Cited by 18 publications

References 34 publications

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

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

Click Inspired Synthesis of Novel Cinchonidine Glycoconjugates as Promising Plasmepsin Inhibitors

Organocatalytic [3+2] Cycloadditions: Toward Facile Synthesis of Sulfonyl-1,2,3-Triazolyl and Fully Substituted 1,2,3-Triazolyl Glycoconjugates

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