6341-06-6

Upstream product

• 6032-23-1 L-arabino-[2]hexosulose bis-phenylhydrazone 
• 5440-70-0 L-(1S)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-erythritol 
• 46994-10-9 4-(D-xylo-tetritol-1-yl)-2-phenyl-2H-1,2,3-triazole 
• 15476-34-3 L_r-1cat_F-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-butane-1c_F,2t_F,3r_F,4-tetraol 
• 50-99-7 D-glucose 
• 100-63-0 phenylhydrazine 
• 2280-44-6 D-Glucose 
• 67-56-1 methanol 
• 534-97-4 glucosazone 
• 7732-18-5 water 

Downstream Products

• 5440-70-0 DL-(1RS)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-erythritol 
• 3213-80-7 2-phenyl-1,2,3-triazole-4-carboxaldehyde 
• 188964-33-2 β-D-erythrofuranosyl-2-phenyl-2H-1,2,3-triazole 
• 18402-97-6 α-D-erythrofuranosyl-2-phenyl-2H-1,2,3-triazole 
• 6206-85-5 2-phenyl-1,2,3-triazole-4-formaldehyde oxime 
• 3359-24-8 2-(2-phenyl-2H-1,2,3-triazole-4-yl)methanol 
• 1578191-48-6 4-(ethoxymethyl)-2-phenyl-2H-1,2,3-triazole 
• 1578191-50-0 4-(butoxymethyl)-2-phenyl-2H-1,2,3-triazole 
• 1578191-46-4 (2-phenyl-2H-1,2,3-triazole-4-yl)methyl benzoate 
• 329695-11-6 (2-phenyl-2H-1,2,3-triazole-4-yl)methyl acetate 
• 1578191-44-2 (2-phenyl-2H-1,2,3-triazole-4-yl)methyl hexanoate 
• 1578191-43-1 (2-phenyl-2H-1,2,3-triazole-4-yl)methyl decanoate 
• 1339003-34-7 2-phenyl-4-vinyl-2H-1,2,3-triazole 
• 6206-85-5 (E)-2-phenyl-2H-1,2,3-triazole-4-carbaldehyde oxime 

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.

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.

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