Emerging aspects of Triazole in Organic Synthesis: Exploring its Potential as a Gelator.

Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) - commonly known as the "click reaction" - serves as the most effective and highly reliable tool for facile construction of simple to complex designs at the molecular level. It relates to the formation of carbon heteroatomic systems by joining or clicking small molecular pieces together with the help of various organic reactions such as cycloaddition, conjugate addition, ring-opening, etc. Such dynamic strategy results in the generation of triazole and its derivatives from azides and alkynes with three nitrogen atoms in the five-membered aromatic azole ring that often form gel assembled structures having gelating properties. These scaffolds have led to prominent applications in designing advanced soft materials, 3D printing, ion sensing, drug delivery, photonics, separation, and purification. In this review, we mainly emphasize on the different mechanistic aspects of triazole formation which includes synthesis of sugar-based and non-sugar-based triazoles, and their gel applications reported in the literature for the past ten years, as well as the upcoming scope in different branches of applied sciences.

Self-assembly of sugar based glyco-lipids: Gelation studies of partially protected d-glucose derivatives.

A series of sugar-based glycolipid derivatives were prepared by N-glycosylamines, and their organogelation property has been analyzed. We have observed the efficient gelation for some of the anilines substituted glycolipids derivatives in different aromatic and aliphatic solvents. It was found that the gelation occurred predominantly in aliphatic solvents with CGC of 0.8% (w/v) attributed to the presence of long alkyl chain in the glycolipids. The structural and morphological properties of the xerogels were investigated by NMR, powder XRD, and FE-SEM respectively. Furthermore, the thermal stability was analyzed by DSC.

Synthesis and antioxidant activity of a novel class of fluorescein-based ß-C-glycosides.

A series of fluorescein-based ß-C-glycosyl ketones were synthesized through aldol condensation of ß-C-glycosyl ketones with fluorescein monoaldehyde under ambient reaction conditions in good yields. Formation of the expected product has been confirmed through different spectral techniques. Fluorescein-based ß-C-glycosides show moderate anti-oxidant activities with maximum inhibitory activity of 60%.

Synthesis and properties of amphiphilic photoresponsive gelators for aromatic solvents.

A sugar-based photoresponsive supergelator, N-glycosylazobenzene that shows selective gelation of aromatic solvents is described. The partial trans-cis isomerization of the azobenzene moiety allows photoinduced chopping of the entangled gel fibers to short fibers, resulting in controlled fiber length and gel-sol transition. The gelator is useful for the selective removal of toxic aromatic solvents from water.

Design, synthesis, and biological evaluation of a novel class of fluorescein-based N-glycosylamines.

A series of fluorescein-based N-glycosylamines was synthesized from the corresponding fluorescein amine and a partially protected d-glucose. The physiochemical investigation of these compounds by spectral and morphological studies reveals their gelation potential. The exclusive localization of fluorescence in the cytoplasm through cell imaging studies reveals the anti-cancer potentials of N-glycosylamines.

Studies on the synthesis of ether-, substituted alkyl-, or aryl-linked C-disaccharide derivatives.

A series of ether-, substituted alkyl-, or aryl-linked disaccharide derivatives have been synthesized in relatively good yield and characterized using different spectral techniques including single-crystal X-ray diffraction (XRD). ß-Anomeric forms of sugar moiety in these derivatives were identified from (1)H NMR studies. The existence of inter- and intramolecular hydrogen bonding interactions were identified from single-crystal XRD studies.

Synthesis of quinoline-based glycoconjugates: a facile one-pot three-component reaction.

A multicomponent one-pot reaction involving propargyl glycosides, methoxy-substituted aromatic aldehydes and aromatic amines using Cu(I) as catalyst is described, which provides an efficient and practical route to synthesize several quinoline-based glycoconjugates in good yield.

Regioselective facile one-pot Friedländer synthesis of sugar-based heterocyclic biomolecules.

Regioselective facile one-pot synthesis of 16 different sugar-based quinoline, naphthyridine, and xanthone derivatives is reported. The compounds are characterized by NMR spectroscopy and elemental analysis. The beta-Anomeric form of the sugar moiety was identified from (1)H NMR studies. Antimicrobial studies of these sugar-heterocyclic derivatives, 3a, 3b, 3f, 5c, 7a, 7b, and 7c show excellent activity against different microbes.

Synthesis and antioxidant activity of a novel class of 4,6-O-protected O-glycosides and their utility in disaccharide synthesis.

BF(3).Et(2)O-catalysed O-glycosylation of 1,2,3-tri-O-acetyl-4,6-O-butylidene- and ethylidene-beta-d-glucopyranose with different aliphatic and aromatic alcohols proceeds for the most part with complete retention of anomeric configuration. Antioxidant activity of O-glycosides shows significant inhibition (IC(50) approximately 77%). 1,3-Dipolar cycloaddition of terminal alkyne derivatives of O-glycosides with glycosyl azide results in disaccharides.

Structural and DNA cleavage of sugar-derived Schiff base ligands and their dinuclear Cu(II) complexes.

Neutral dinuclear Cu(II) complexes of Schiff base ligands derived from D-glucose have been synthesized and structurally characterized. These complexes were evaluated for their interaction with DNA, and DNA cleavage was observed even in the presence of radical inhibitors.

Facile one-pot synthesis of sugar-quinoline derivatives.

Seven different sugar-quinoline derivatives were synthesised in a 'one-pot' reaction from their corresponding C-beta-glycoside derivatives. The compounds were characterised by NMR spectroscopy and elemental analysis.