13733-78-3

Upstream product

• 4292-19-7 1-Iodododecane 
• 10157-76-3 dodecyl 4-methylbenzenesulphonate 
• 112-53-8 1-dodecyl alcohol 
• 112-41-4 1-dodecene 
• 99-24-1 methyl galloate 
• 106-96-7 propargyl bromide 
• 941-55-9 4-toluenesulfonyl azide 
• 18536-91-9 dodecyltriethoxysilane 
• 112-52-7 1-chlorododecane 
• 143-15-7 1-dodecylbromide 

Downstream Products

• 929-73-7 dodecylammonium chloride 
• 935510-27-3 C₁₀₀H₁₂₈ClMnN₁₆ 
• 1207279-61-5 dibenzyl (2S,4R)-4-[(1-dodecyl-1H-1,2,3-triazol-4-yl)methoxy]pyrrolidine-1,2-dicarboxylate 
• 1207737-22-1 C₂₀H₃₇N₃O 
• 1207737-19-6 C₂₁H₃₀N₄O₃ 
• 1207737-21-0 C₂₁H₃₂N₄O 
• 1207737-20-9 C₂₂H₃₃N₃O 
• 1207737-18-5 C₂₇H₃₅N₃O 
• 1020377-58-5 (1-dodecyl-1H-1,2,3-triazol-4-yl)(phenyl)methanone 
• 1009089-52-4 1-(n-dodecyl)-4-(phenyl)-1H-1,2,3-triazole 
• 1310741-06-0 1,2-bis(1-dodecyl-5-iodo-1H-1,2,3-triazol-4-yl)benzene 
• 1310741-03-7 5-bromo-4-(2-(bromoethynyl)phenyl)-1-dodecyl-1H-1,2,3-triazole 
• 1310741-01-5 1,2-bis(5-bromo-1-dodecyl-1H-1,2,3-triazol-4-yl)benzene 
• 1345823-44-0 1-(n-dodecyl)-4-phenethyl-1H-1,2,3-triazole 

Relevant academic research and scientific papers

Hydrogen Bonding-Induced H-Aggregation for Fluorescence Turn-On of the GFP Chromophore: Supramolecular Structural Rigidity

To turn on the fluorescence of the native green fluorescence protein (GFP) chromophore, 4-hydroxybenzylidene-dimethylimidazolinone (HBDI), in an artificial supramolecular system has been a challenging task, because it requires high local environmental rigidity. This work shows that the formation of H-aggregates of an HBDI-containing organogelator results in two orders of magnitude fluorescence enhancement (Φf=2.9 vs. 0.02 %), in which the inter-HBDI OH???OH H-bonds play a crucial role. The aggregation-induced fluorescence enhancement of HBDI has important implications on the origin of the high fluorescence quantum efficiency of HBDI in the GFP β-barrel and on the supramolecular strategy for a full fluorescence recovery of HBDI. These results reveal a new approach to designing rigid chromophore aggregates for high-performance optoelectronic properties.

Synthesis of 6-thio pseudo glycolipids and their orientation on a gold slide studied by IRRAS

We have synthesized four 6-thio pseudo glycolipid analogues and assessed how two of them self-assembled on a gold surface. These structures were designed as candidate tethers molecules to anchor bilayer lipid membranes on gold. 6-Deoxy-6-thiogalactose was chosen to anchor the macromolecule to the gold and define an aqueous zone at the gold surface. A long alkane chain (C-12 or C-18) linked to the anomeric position of the sugar residue was chosen to anchor a bilayer lipid membrane. The linkage between the carbohydrate and the hydrophobic chains is either a glycosidic bond or a 1,4-disubstituted triazole formed by copper(I)-catalysed alkyne-azide cycloaddition (CuAAC) of the propargyl glycoside with azido-dodecane and azido-octadecane. We are expecting that the hydrocarbon chains will orient themselves perpendicular to the gold surface and be incorporated into the first leaflet of the bilayer membrane. We have studied self assembled monolayers of the C-12 aglycone analogues on gold using infrared reflection absorption spectroscopy (IRRAS). We compared the results given by the IRRAS experiments to the IR spectra recorded by attenuated total reflection (ATR) spectroscopy on films of the randomly oriented analogues. Our results demonstrate that the C-12 analogues did bind to gold and did orient themselves perpendicular to the gold slide.

Mode of action investigation for the antibacterial cationic anthraquinone analogs

Reported previously by our group, we have developed a novel class of antibacterial cationic anthraquinone analogs with superb potency (MIC 1 μg/mL) against Gram positive (G+) pathogens including Methicillin-resistant Staphylococcus aureus (MRSA). However, most of these compounds only manifest modest antibacterial activity against Gram negative (G-) bacteria. Further investigation on the antibacterial mode of action using fluorogenic dyes reveals that these compounds exert two different modes of action that account for the difference in their antibacterial profile. It was found that most of the compounds exert their antibacterial activity by disrupting the redox processes of bacteria. At high concentration, these compounds can also act as membrane disrupting agents. This information can help to design new therapeutics against various bacteria.

Thiophenol-formaldehyde triazole causes apoptosis induction in ovary cancer cells and prevents tumor growth formation in mice model

In the present study a library of thiophenol-formaldehyde-triazole (TFT) derivatives was synthesized and screened against CAOV3, CAOV4 and ES-2 ovary cancer cell lines. Initial screening revealed that five-compounds 5a, 5b, 5j, 5h and 5i inhibited the viability of tested cell lines. Analysis of apoptosis revealed that increase in compound 5a (most active) concentration from 0.25 to 2.0 μM enhanced apoptotic cell proportion. Transwell assay showed reduction in invasive potential of CAOV3 cells on treatment with compound 5a. In wound healing assay increasing the concentration of compound 5a from 0.5 to 2.0 μM caused a significant (P 0.05) decrease in the migration potential. Western blotting showed that compound 5a treatment markedly decreased the level of matrix metalloproteinase (MMP)-2 and ?9 in CAOV3 cells. Treatment of CAOV3 cells with compound 5a caused a marked decrease in Focal Adhesion Kinase (FAK) activation. Tumor growth was inhibited in the compound 5a treated mice markedly than those of untreated group. The tumor metastasis to liver, intestine, spleen and peritoneal cavity was markedly decreased in mice treated with 10 mg/kg dose of compound 5a. Examination of Von Willebrand factor (vWF) expression in liver, intestinal and pulmonary lesions showed a marked decrease in the compound 5a-treated mice. The infiltration of macrophages in the metastatic lesions showed a significant decrease in compound 5a-treated mice. In conclusion, the compound 5a inhibited ovary cancer cell viability and induced apoptosis through decrease in expression of vWF and metalloproteinase, suppression of FAK activation and decrease in infiltration of macrophages. The compound 5a therefore can be investigated further for the treatment of ovary cancer.

Library synthesis and antibacterial investigation of cationic anthraquinone analogs

We report the parallel synthesis of a series of novel 4,9-dioxo-4,9- dihydro-1H-naphtho[2,3-d][1,2,3]triazol-3-ium chloride salts, which are analogs to cationic anthraquinones. Three synthetic protocols were examined leading to a convenient and facile library synthesis of the cationic anthraquinone analogs that contain double alkyl chains of various lengths (C2-C 12) at N-1 and N-3 positions. The antibacterial activities of these compounds were evaluated against Gram-positive bacterium Staphylococcus aureus and Gram-negative bacterium Escherichia coli. The antibacterial activities of these compounds were expected to be associated with the structural features of naphthoquinone, cation and lypophilic alkyl chain and, interestingly, they showed much higher levels of antibacterial activities against G+ than G- bacteria. In addition, when the total number of carbon atoms of the alkyl groups at both N-1 and N-3 positions lies between 9 and 18, the bactericidal activity against S. aureus increased with increasing alkyl chain length at both N-atoms with MIC ≥ 1 μg/mL.

SYNTHESE D'AZOTURES D'ALKYLES A LONGUES CHAINES ET ETUDE DE LEUR AGREGATION EN SOLUTION DANS LE FORMAMIDE

A new method for synthesis of alkyl azides is described.These compounds with long alkylchains, insoluble in water, are surfactants and micellize in formamide.

1-Alkyl-3-methyl-1,2,3-triazolium [NTf2] ionic liquids: synthesis and properties

A series of 1-alkyl-3-methyl-1,2,3-triazolium bis(trifluoromethylsulfonyl)imide [NTf2] ionic liquids were prepared synthetically using azide-alkyne 'click' cyclization chemistry and their physicochemical and thermal properties were determined. Increasing the alkyl chain length resulted in increased viscosities and higher thermal transitions (Tg or Tm) with depressed molar conductivities. Walden plot analysis indicated that the ionicity of 1-butyl-3-methyl-1,2,3-triazolium [NTf2] was comparable to the analogous imidazolium system and higher than the 1,2,4-triazolium equivalent.

Zwitterionic and mesoionic liquids: Molecular aggregation in 3-methylsydnone

Ionic liquids are green solvents with interesting properties: displaying low melting points and high boiling points. They offer a new approach applicable in many instances. Nevertheless, the presence of free ions can be a matter in some cases, e.g. for the study of nucleophilic reactions, in electrochemistry, and in each situation where there is a competition between counter ions, as in micellization of ionic surfactants. Neutral compounds having formal unit electrical charges of opposite sign, and the same physical properties than ionic liquids would be a nice alternative to these latter solvents. There are two classes of chemical compounds having these characteristics: zwitterionic liquids (with no uncharged canonical representation) and mesoionic liquids (in which the negative and the positive charges are delocalized). In that last class we have chosen to work with 3-methylsydnone in order to examine, in this aprotic solvent, if it was possible to observe aggregation of surfactants in the same manner as in water. With all kinds of surfactants studied (ionic, zwitterionic and mesoionic) we have been able to demonstrate the formation of direct micelles: hydrogen bonding is thus not mandatory for molecular aggregation. Comparison of the behavior in water and in formamide showed that solvophobic interactions were qualitatively comparable but with a lower intensity.

Revealing the nature of thio-click reactions on the solid phase

Thiol- and yne-functionalized beads were manufactured in a simple microfluidic setup. While CuAAC and thiol-yne reactions were performed on yne-functionalized beads, 9 different thiol-X reactions were compared, in terms of kinetics and conversion, on thiol-functionalized beads. The Royal Society of Chemistry 2011.

Synthesis of amphiphilic graphitic silver nanoparticles with inherent internal standards: an efficient strategy for reliable quantitative SERS analysis in common fluids

An efficient strategy for reliable quantitative SERS analysis in common fluids was proposed by amphiphilic functionalization of graphitic silver nanoparticles with inherent internal standards by azides, and has the merits of high accuracy, enhanced dispersity and outstanding stability in fluids.