Applications of Click Chemistry in Drug Discovery and Development

Gopalan, Balasubramanian; Balasubramanian, K. K.

doi:10.1002/9783527694174.ch2

Cited by 13 publications

(18 citation statements)

References 149 publications

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“…Instantly, after the discovery of click chemistry by two independent research groups, Meldal and Sharpless , 1,2,3‐triazole heterocycle, recognized as the most popular and important scaffold because of their wide applications in different fields. Since then, click inspired heterocyclic system continuously employed to find a potential drug candidate where a large number of bioactive 1,2,3‐triazoles with a good bioactivity profile are reported in recent years . The click chemistry, being highly efficient, reliable and modular approach, generates a plethora of novel compounds with apparent ease thereby facilitates lead discovery and optimization process.…”

Section: Introductionmentioning

confidence: 99%

“…The click chemistry, being highly efficient, reliable and modular approach, generates a plethora of novel compounds with apparent ease thereby facilitates lead discovery and optimization process. Moreover, the product 1,4‐disubstituted 1,2,3‐triazole skeleton, itself, is a well known pharmacophore .…”

Section: Introductionmentioning

confidence: 99%

“…The strong dipole moment of oxadiazoles facilitates their hydrogen bonding interactions with various receptors therefore contributes significantly towards pharmacophoric activities . Various structural modifications have been carried out to alter the inherent reactivity of this potent building block to create novel lead compounds . In fact, a number of potent drugs composed of 1,3,4‐oxadiazole skeleton are already available in the market, for example, Zibotentan (an anticancer drug) , Raltegravir or MK‐0518 (an anti‐HIV drug) , and tiodazosin (an anti‐hypertensive drug) .…”

Section: Introductionmentioning

confidence: 99%

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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%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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 click approach using thermodynamically tested CuAAC exhibits exclusive characteristics (e.g., better tolerance for many functional entities and pH fluctuations, facile and milder reaction settings, and compatibility with diverse solvents along with water). These preferred traits make CuAAC a powerful tool for designing, developing, and reshaping complex organic entities of biological relevance. − …”

Section: Introductionmentioning

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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“…[8][9][10] The structure and regiochemistry of the products 6 were established by using NMR spectroscopy and confirmedb yt he X-ray structure analysisof6ag ( Figure S2). The OrgVACC reactiono fh ydrogen-, methyl-, methoxy-, chloro-, andn itro-substituted arylketones 1e-i with 7a under the catalysis of 3e furnished the fully decorated N-vinyl-1,2,3-triazoles 8ea-ia in 70-92 %y ields, which showed the negligible effect of the electronic factors (Table 4, entries [4][5][6][7][8]. The OrgVACC reactiono f1a with 7a under the optimized conditions furnished the expected N-vinyl-1,2,3-triazole 8aa in 85 %y ield (Table 4, entry 1).…”

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confidence: 99%