Photo-responsive organogelator based on cholesterol incorporated sugar-azobenzene derivatives.

In this report, the design and synthesis of cholesterol-based sugar azobenzene derivatives as photo-responsive organogelators have been carried out. The gel formation in different solvents was examined, and a minimum CGC of 0.5 % (w/v) was attained in toluene.

Smart supramolecular photoresponsive gelator with long-alkyl chain azobenzene incorporated sugar derivatives for recycling aromatic solvents and sequestration of cationic dyes.

Phase-selective gelation of low molecular-weight photoresponsive organogelator possessing long aliphatic chain azobenzene sugar derivatives and its applications in the recycling of aromatic solvents and also the removal of cationic dyes is reported. Very low critical gelation concentration (CGC) in aromatic solvents implies that it acts as a very good gelator. The photoinduced gel-to-sol transition was attained by irradiation with UV light at 350 nm.

Sugar-Based Phase-Selective Supramolecular Self-Assembly System for Dye Removal and Selective Detection of Cu Ions.

Simple, effective, and eco-friendly sugar-based phase-selective gelators were synthesized at a low cost. They showed high gelling ability toward a wide range of solvents at lower concentrations (minimum gelation concentration ∼0.3%).

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 forms gel-assembled structures having gelating properties.

Sugar-benzohydrazide based phase selective gelators for marine oil spill recovery and removal of dye from polluted water.

The synthesis of 3,4,5-tri-O-benzohydrazide based N-glycosylamines were characterized using NMR (H and C) and mass spectral analysis. Gelation properties of the synthesized molecules in different solvents and oils were studied and gelation was observed with minimum Critical Gelator Concentration (CGC) of 0.8% (w/v) in benzene.

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.

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

A series of fluorescein-based β-C-glycosyl ketones were synthesized through aldol condensation of β-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 β-C-glycosides show moderate anti-oxidant activities with maximum inhibitory activity of 60%.

A concise pathway to synthesize a novel class of pyrido(2,3-d)pyrimidine-C-β-D-glycosides.

A concise pathway to synthesize a novel class of nine different pyrido(2,3-d)pyrimidine-C-β-d-glycosides is reported. Formation of Michael adduct as an intermediate followed by heterocyclization are the key steps and the products were characterized by different spectral studies. β-Anomeric forms of C-glycosides were assigned from 1H NMR spectroscopy.

A facile one-pot synthesis of biphenyl methyl-C-β-D-glycosides.

Facile one-pot synthesis of biphenyl methyl-C-β-D-glycosides was carried out using 4,6-O-protected-C-glycoside, aromatic aldehydes and malononitrile in pyrrolidine as an organocatalyst. Studies reveal that the use of pyrrolidine resulted in a better yield.

A novel class of sugar-based ether-linked-dispirooxindolo-pyrrolidines/pyrrolizidines through [3+2]-cycloaddition of azomethine ylides.

An efficient one-pot synthesis of novel sugar based dispirooxindolo-pyrrolidines/pyrrolizidines has been accomplished by a [3+2]-cycloaddition. This method utilizes an azomethine ylide derived from isatin and sarcosine/l-proline, with an ether linked α-,β-unsaturated-β-C-glycosidic ketones as the dipolarophile. All these sugar-based heterocyclics were characterized by NMR ((1)H and (13)C) and elemental analysis.

Studies on a novel class of triaryl pyridine N-glycosylamine amphiphiles as super gelators.

A novel class of six different triaryl pyridine N-glycosylamine amphiphiles was synthesised and characterized based on different spectral techniques, such as NMR and mass analysis. Gelation properties in different aromatic and aliphatic solvents were studied and gelation was observed predominantly in aliphatic solvents with CGC of 0.5% (w/v) and is attributed to the presence of long alkyl chain.

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.

FACE-selective fluorogenic cycloaddition reaction between coumarin azides and sugar terminal alkynes: an experimental and computational study.

Copper catalyzed azide-alkyne cycloaddition reaction (CuAAC) of non-fluorescent coumarin azides and sugar terminal alkynes afforded intense fluorescent 1,2,3-triazoles in 75-85% of yield. The photophysical properties of coumarin-sugar triazoles influenced greatly, upon introducing different substituents at 6th and 7th positions. The experimental observations were further supported by TD-DFT computational studies.

Studies on the synthesis and the antimicrobial and antioxidant activities of a novel class of fluorescein-based glycosides.

Facile glycosylation of a fluorescein diol derivative with per-O-acetyl/benzoyl sugar derivatives using BF(3)·Et(2)O catalyst resulted in the formation of the expected glycosides in 54-66% yield. The biological screening of the glycosides against different microbes shows good inhibitory activity. The antioxidant activity of the fluorescein-based glycosides shows remarkable inhibition (IC(50) ∼80%).

A facile synthesis of sugar-pyrazole derivatives.

A facile synthesis of sugar-pyrazole derivatives has been accomplished by condensation of sugar-chalcone with hydrazine hydrate under neutral conditions resulting in yields of 70-85%. The products are characterized by FTIR and NMR spectroscopy and by elemental analysis. The β-anomeric forms for these derivatives were assigned by NMR spectroscopy.

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.

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.

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). β-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.

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.

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%).

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.