534-97-4

Usage

Uses

Used in Carbohydrate Chemistry:
D-arabino-hexosulose bis(phenylhydrazone) is used as a reagent for the identification and quantification of sugars due to its ability to form stable complexes with them.
Used in Biochemical Research:
D-arabino-hexosulose bis(phenylhydrazone) is used as a valuable tool in carbohydrate analysis, aiding in the study of sugar structures and their interactions.
Used in Pharmaceutical Research:
D-arabino-hexosulose bis(phenylhydrazone) is studied for its potential biological activities, which may lead to applications in the development of new pharmaceuticals.

Upstream product

• 117898-98-3 S-ethyl-1-thio-D-fructose 
• 64-19-7 acetic acid 
• 100-63-0 phenylhydrazine 
• 576-69-2 Fructose-1-phosphate 
• 57-48-7 D-Fructose 
• 50-99-7 D-glucose 
• 492-61-5 β-D-glucose 
• 492-62-6 alpha-D-glucopyranose 
• 7664-93-9 sulfuric acid 
• 6198-73-8 methyl 3,4-anhydro-β-D-galactopyranoside 
• 2280-44-6 D-Glucose 
• 19057-60-4 mixture of 3-O-β-chacotriosides of diosgenin and yamogenin 
• 65604-80-0 mixture of 3-O-<α-L-rhamnopyranosyl-(1->2)><β-D-xylopyranosyl(1->3)>-β-D-glucopyranosides of diosgenin and yamogenin 
• 54522-52-0 26-O-β-D-glucopyranosyl-22-O-methylfurost-5-ene-3β,26-diol 3-O-β-chacotrioside 

Downstream Products

• 26706-42-3 tetra-O-acetyl-aldehydo-keto-D-arabino-[2]hexosulose-bis-phenylhydrazone 
• 26706-41-2 (2R,3S,4R)-6-(Methyl-phenyl-hydrazono)-5-(phenyl-hydrazono)-hexane-1,2,3,4-tetraol 
• 1071668-15-9 O⁵-methyl-D-arabino-[2]hexosulose-bis-phenylhydrazone 
• 122147-44-8 1,5-Diphenyl-3-(N'-phenyl-D-arabinonohydrazonoyl)-formazan 
• 3673-07-2 1,2-diamino-1,2-dideoxy-D-mannitol 
• 643-71-0 D-glucosone 
• 3673-11-8 1,2-bis-salicylidenamino-1,2-dideoxy-D-mannitol 
• 84039-47-4 D-arabino-hexose (p-bromophenyl)osotriazole 
• 35522-78-2 D-ribo-3,6-anhydro-[2]hexosulose-bis-phenylhydrazone 
• 35522-79-3 D-arabino-3,6-anhydro-[2]hexosulose-bis-phenylhydrazone 
• 100738-94-1 2-phenylazo-1-(N'-phenyl-hydrazino)-D-ribo-1,5-anhydro-2-deoxy-hex-1-enitol 
• 165199-07-5 O⁵,O⁶-isopropylidene-D-arabino-[2]hexosulose-bis-phenylhydrazone 
• 3082-92-6 5-(1,2-diacetoxy-ethyl)-1-phenyl-1H-pyrazole-3-carbaldehyde acetyl-phenyl-hydrazone 
• 13306-99-5 2-phenyl-2H-[1,2,3]triazole-4-carboxylic acid 

Relevant academic research and scientific papers

A fine-tuned lipophilicity/hydrophilicity ratio governs antibacterial potency and selectivity of bifurcated halogen bond-forming nbtis

Herein, we report the design of a focused library of novel bacterial topoisomerase inhibitors (NBTIs) based on innovative mainly monocyclic right-hand side fragments active against DNA gyrase and Topo IV. They exhibit a very potent and wide range of antibacterial activity, even against some of the most concerning hard-to-treat pathogens for which new antibacterials are urgently needed, as reported by the WHO and CDC. NBTIs enzyme activity and whole cell potency seems to depend on the fine-tuned lipophilicity/hydrophilicity ratio that governs the permeability of those compounds through the bacterial membranes. Lipophilicity of NBTIs is apparently optimal for passing through the membrane of Gram-positive bacteria, but the higher, although not excessive lipophilicity and suitable hydrophilicity seems to determine the passage through Gram-negative bacterial membranes. However, due to the considerable hERG inhibition, which is still at least two orders of magnitude away from MICs, continued optimization is required to realize their full potential.

Searching for new drugs for Chagas diseases: triazole analogs display high in vitro activity against Trypanosoma cruzi and low toxicity toward mammalian cells

Chagas disease is one of the most relevant endemic diseases in Latin America caused by the flagellate protozoan Trypanosoma cruzi. Nifurtimox and benzonidazole are the drugs used in the treatment of this disease, but they commonly are toxic and present severe side effects. New effective molecules, without collateral effects, has promoted the investigation to develop new lead compounds with to advance for clinical trials. Previously, 3-nitro-1H-1,2,4-triazole-based amines and 1,2,3-triazoles demonstrated significant trypanocidal activity against T. cruzi. In this paper, we synthesized a new series of 92 examples of 1,2,3-triazoles. Six compounds exhibited antiparasitic activity, 14, 25, 27, 31 and 40, 43 and were effective against epimastigotes of two strains of T. cruzi (Y and Dm28-C) and 25, 27 and 31 exhibited trypanocidal activity similar to benzonidazole. Notably, the compound 25 compared to benzonidazole increase the toxicity against T. cruzi, with no apparent toxicity to the cell line of mice macrophages or primary mice peritoneal macrophages. As results, we calculated selectivity indexes up to 2000 to 25 and 31 in both T. cruzi strains. Derivative 14 caused a trypanostatic effect because it did not damage external epimastigote membrane. Triazoles 40 and 43 impaired parasites viability using a pathway not dependent on ROS production.

1-Aryl-1H- and 2-aryl-2H-1,2,3-triazole derivatives blockade P2X7 receptor in?vitro and inflammatory response in?vivo

Fifty-one 1,2,3-triazole derivatives were synthesized and evaluated with respect to P2X7 receptor (P2X7R) activity and its associated pore. These triazoles were screened in vitro for dye uptake assay and its cytotoxicity against mammalian cell types. Seven 1,2,3-triazole derivatives (5e, 6e, 8h, 9d, 9i, 11, and 12) potently blocked P2X7 receptor pore formation in vitro (J774.G8 cells and peritoneal macrophages). All blockers displayed IC50 value inferior to 500 nM, and they have low toxicity in either cell types. These seven selected triazoles inhibited P2X7R mediated interleukin-1 (IL-1β) release. In particular, compound 9d was the most potent P2X7R blocker. Additionally, in mouse acute models of inflammatory responses induced by ATP or carrageenan administration in the paw, compound 9d promoted a potent blocking response. Similarly, 9d also reduced mouse LPS-induced pleurisy cellularity. In silico predictions indicate this molecule appropriate to develop an anti-inflammatory agent when it was compared to commercial analogs. Electrophysiological studies suggest a competitive mechanism of action of 9d to block P2X7 receptor. Molecular docking was performed on the ATP binding site in order to observe the preferential interaction pose, indicating that binding mode of the 9d is by interacting its 1,2,3-triazole and ether moiety with positively charged residues and with its chlorobenzene moiety orientated toward the apolar end of the ATP binding site which are mainly composed by the Ile170, Trp167 and Leu309 residues from α subunit. These results highlight 9d derivative as a drug candidate with potential therapeutic application based on P2X7 receptor blockade.

1-Phenyl-1H- and 2-phenyl-2H-1,2,3-triazol derivatives: Design, synthesis and inhibitory effect on alpha-glycosidases

Due to aging and increasingly overweight in human population, the incidence of non-insulin dependent diabetes mellitus (NIDDM or Type 2 DM) is increasing considerably. Therefore, searching for new α-glycosidase inhibitors (GIs) capable of slowing down carbohydrate assimilation by humans is an important strategy towards control of NIDDM. In this report, we disclose the search for new easily accessible synthetic triazoles as anti-diabetic compounds. Two series of non-glycosid triazoles were synthesized (series A and B) and screened against baker's yeast α-glucosidase (MAL12) and porcine pancreatic α-amylase activity (PPA). Of the 60 compounds tested at 500 μM, were considered hits (≥60% inhibition) six triazoles against MAL12 and three against PPA, with the inhibition reaching up to 99.4% on MAL12 and 88.6% on PPA. The IC50 values were calculated for both enzymes and ranged from 54 to 482 μM for MAL12 and 145 to 282 μM for PPA. These results demonstrated the potential activity of simple and non-glycosidic triazoles as an important novel class of GIs for the development of drugs to treat Type 2 DM.

Determination of glyceraldehyde formed in glucose degradation and glycation

Glyceraldehyde (GLA) was determined in glucose degradation and glycation. GLA was detected as a decahydroacridine-1,8-dione derivative on reversed phase HPLC using cyclohexane-1,3-dione derivatizing reagent. The glucose-derived GLA level was higher than the glycation-derived GLA level, because GLA was converted to intermediates and advanced glycation end products (AGE) in glycation. GLA was also generated from 3-deoxyglucosone and glucosone as intermediates of glucose degradation and glycation. This study suggests that glyceraldehyde is generated by hyperglycemia in diabetes, and that it is also formed in medicines such as peritoneal dialysis solution.

Highly efficient and selective biocatalytic acylation studies on triazolylsugars

Different acid anhydrides (of C2 to C7 aliphatic fatty acids and benzoic acid) have been used to study the selective acylation of primary/secondary hydroxyl groups in 2-phenyl-4-(D-threo-1′,2′, 3′-trihydroxypropyl)-2H-1,2,3-triazole, 2-phenyl-4-(D-erythro-1′, 2′,3′-trihydroxypropyl)-2H-1,2,3-triazole, 2-phenyl-4-(D-arabino- 1′,2′,3′,4′-tetrahydroxybutyl)-2H-1,2,3-triazole and 2-phenyl-4-(D-lyxo-1′,2′,3′,4′-tetrahydroxybutyl)-2H-1, 2,3-triazole in the presence of Candida antarctica lipase B in diisopropyl ether. Among the different acid anhydrides, butanoic anhydride was found to be the most efficient acylating agent (for butanoylation); for acetylation, vinyl acetate gave the best results. The reactions with both these acylating agents were highly selective and efficient yielding exclusively the monoacylated products in 95-99% yields in 1-5 h.

Novel lipase-catalysed highly selective acetylation studies on D-arabino- and D-threo-polyhydroxyalkyltriazoles

Capabilities of lipases from Candida antarctica, Candida rugosa and porcine pancreas have been evaluated for regioselective acetylation of 2-phenyl-4-(D-arabino-tetrahydroxybutyl)-2H-1,2,3-triazole, 2-phenyl-4-(D-arabino-O-1',2'-isopropylidene-3',4'-dihydroxybutyl)-2H-1,2,3-triazole and 2-phenyl-4-(D-threo-trilhydroxypropyl)-2H-1,2,3-triazole, precursors for the synthesis of triazolylacylonucleosides. C. antarctica lipase and porcine pancreatic lipase exhibited exclusive selectivity for the acetylation of primary hydroxyl group over secondary hydroxyl group(s) in all three cases. Copyright

Synthesis and antiviral activity evaluation of novel 2-phenyl-4-(D-arabino-4′-cycloaminobutyl)triazoles: Acyclonucleosides containing unnatural bases

Five 2-phenyl-4-(D-arabino-4′-cycloamino-3′-hydroxy-O-1′,2′-isopropylidenebutyl)-2H-1,2,3-triazoles, acyclonucleosides containing unnatural bases have been synthesised by opening of the epoxide ring of 2-phenyl-4-(D-arabino-3′,4′-epoxy-O-1′,2′-isopropylidenebutyl)-2H-1,2,3-triazole with the corresponding cyclic amine in 70-85% yields. The starting arabino-epoxytriazole was prepared in five steps starting from D-glucose in an overall yield of 15%. All the five triazolylacycllonucleosides were unambiguously identified on the basis of their spectral data. The structure of one of the intermediates, that is 2-phenyl-4-(D-arabino-1′,2′,3′,4′-tetrahydroxybutyl)-2H-1,2,3-triazole was confirmed by its X-ray crystallographic studies. These acyclonucleosides were subjected to antiviral evaluation in CEM-SS cell-based anti HIV assay with the lymphocytropic virus strains HIV-1IIIB and HIV-1RF. Copyright

Hydrophilically functionalized pyrazoles from sugars

An effective and convenient protocol has been developed for the conversion of D-glucose and 6-O-α-D-glucopyranosyl-D-fructose (palatinose, isomaltulose) into 5-[(1'S)-1','2/-dihydroxyethyl]-1-phenylpyrazole-3-carboxaldehyde (4) and 5-[(1'S)-2-(α-D-glucopyranosyloxy)-1-hydroxethyl])-1-phenylpyrazole-3 -carboxaldehyde (5), key steps being the acetic anhydride-promoted dehydrative cyclization of the respective phenylosazones, and subsequent liberation of the N-acetylphenylhydrazone-blocked aldehyde function. Exploitation of the ensuing chemistry of 4 and 5 led to a variety of pyrazole building blocks with a diverse level of hydrophilic substituents (hydroxymethyl, dihydroxyethyl or glucosyl residues) and useful functional groups, such as chloro, cyano, aminomethyl, vinyl and acryloyl moieties.