2025

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Copper(I)-Catalyzed Tandem One-Pot Synthesis of Bis(1,2,3-Triazoles) and Tetrakis (1,2,3-Triazole) Glycoconjugates
(John Wiley and Sons Inc, 2025) Vinay Kumar Pandey; Manoj K. Jaiswal; Danish Ansari; Mangal S. Yadav; Shristy Maurya; V. K. Tiwari
The work describes the copper (I)-catalyzed convenient synthesis of 5,5′-bis-1,2,3-triazoles by reacting glycosyl azides with terminal alkynes in the presence of di-tert-butyl peroxide (DTBP) as oxidant in refluxing toluene. The reaction proceeds through intramolecular ‘click’ followed by Csp2.Csp2 bond formation in the successive steps under one-pot conditions. The devised protocol is further extended to access biocompatible tetrakis(1,2,3-triazolyl) sialoconjugates under a two-step pathway followed by Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. The developed glycoconjugates have been characterized using extensive spectroscopic analysis, including NMR (1H & 13C), IR, and high-resolution mass spectrometry data, and also a single-crystal X-ray of compound 5e. Notably, the reaction proceeds in a one-pot fashion with a high atom economy, where a wide substrate scope with diversity in products finally validates the importance of the devised protocol. © 2025 Wiley-VCH GmbH.
Designing DPP-4 inhibitors: Synthesis, characterization, in silico & in vitro evaluation, and theoretical calculation of flexible compounds linked via ortho xylyl spacers
(Elsevier B.V., 2025) Vipin Kumar; Manisha Nidhar; Muhammad Sheraj; Vishal Prasad Sharma; Priya Gupta; Rahul Kumar Singh; Ashish Kumar Tewari
In this study, 1,2,3-triazole-containing six symmetrical flexible dimer compounds (5a-5f) linked via ortho xylyl spacers were synthesized using a copper-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction. Triazinone, isatin, and pyridazinone moieties were utilized to synthesize the heteroaromatic terminal alkynes (3a-3f). The structural characterization of all compounds was performed using spectroscopic techniques, including SCXRD, 1H and 13C-NMR, IR, and HRMS spectrometry. Among these compounds, compound 5a was crystallized, showing two twisted boat-type geometries at an angle of 43.98 degrees. Moreover, we investigated the intra- and intermolecular contact preserving the crystal packing in the solid state. Hirshfeld surface analysis and its related 2-D fingerprint plots control the percentage contribution of intermolecular contact. The in silico study of these compounds was conducted and revealed that 5d and 5c have good docking scores and interactions; further, all these compounds were validated by in vitro DPP-4 inhibitory activity. DPP-4 inhibition revealed that compound 5d has an IC50 value of 1.57 nM, similar to the standard drug sitagliptin. Compound 5d could be a potent DPP-4 inhibitor with antidiabetic potential for further investigation. © 2025
Growing impact of ‘Click chemistry’ inspired glycohybrid 1,2,3-Triazoles in organic synthesis
(Elsevier Ltd, 2025) Sumit Kumar Singh; Anindra Sharma; Nidhi Mishra; V. K. Tiwari
Carbohydrates, a most abundant natural product have fascinating structural features notably their high functional nature having multiple hydroxyl groups as well stereogenic centers which all together attracted the interest of synthetic chemists to explore them as valuable scaffolds in ligand design. In recent years, 1,2,3-triazole-linked sugar conjugates developed via regioselective CuAAC route have emerged as promising ligands in transition metal catalysis. These glycoconjugates have been applied in C–C and C–N bond-forming reactions, including Ullmann and Sonogashira couplings, particularly with Cu, Ni, and Pd catalysts. Their use has further extended to asymmetric catalysis, ligand-assisted activation, and sustainable synthesis. This review provides a concise overview of click-derived 1,2,3–triazole–sugar conjugates as promising ligands in transition metal catalysis, with highlighting their role in enhancing the catalytic reactivity, controlling the regio- and/or stereoselectivity, and improving the efficiency of metal-mediated transformations. © 2025 Elsevier Ltd