- Hydrogen Bonding-Induced H-Aggregation for Fluorescence Turn-On of the GFP Chromophore: Supramolecular Structural Rigidity
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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.
- Tsai, Meng-Shiue,Tsai, Sung-Yu,Huang, Yi-Fan,Wang, Chien-Lung,Sun, Shih-Sheng,Yang, Jye-Shane
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- Synthesis of 6-thio pseudo glycolipids and their orientation on a gold slide studied by IRRAS
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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.
- Guillemineau, Mickael,Singh, Serena,Grossutti, Michael,Auzanneau, France-Isabelle
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- Mode of action investigation for the antibacterial cationic anthraquinone analogs
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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.
- Chan, Ka Yee,Zhang, Jianjun,Chang, Cheng-Wei Tom
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- Thiophenol-formaldehyde triazole causes apoptosis induction in ovary cancer cells and prevents tumor growth formation in mice model
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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.
- Jia, Yan,Si, Lihui,Lin, Ruixin,Jin, Hongjuan,Jian, Wenwen,Yu, Qing,Yang, Shuli
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- Library synthesis and antibacterial investigation of cationic anthraquinone analogs
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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.
- Fosso, Marina Y.,Chan, Ka Yee,Gregory, Rylee,Chang, Cheng-Wei Tom
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- SYNTHESE D'AZOTURES D'ALKYLES A LONGUES CHAINES ET ETUDE DE LEUR AGREGATION EN SOLUTION DANS LE FORMAMIDE
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A new method for synthesis of alkyl azides is described.These compounds with long alkylchains, insoluble in water, are surfactants and micellize in formamide.
- Marti, M. J.,Rico, I.,Ader, J. C.,Savignac, A. de,Lattes, A.
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- 1-Alkyl-3-methyl-1,2,3-triazolium [NTf2] ionic liquids: synthesis and properties
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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.
- Reeder, Zachary K.,Adler, Abigail M.,Miller, Kevin M.
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- Zwitterionic and mesoionic liquids: Molecular aggregation in 3-methylsydnone
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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.
- Cassel, Stephanie,Rico-Lattes, Isabelle,Lattes, Armand
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- Revealing the nature of thio-click reactions on the solid phase
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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.
- Gokmen, M. Talha,Brassinne, Jeremy,Prasath, R. Arun,Du Prez, Filip E.
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- Synthesis of amphiphilic graphitic silver nanoparticles with inherent internal standards: an efficient strategy for reliable quantitative SERS analysis in common fluids
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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.
- Song, Zhi-Ling,Dai, Xin,Li, Mengru,Song, Zhen,Chen, Zhuo,Luo, Xiliang
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- Synthesis and properties of l-valine based chiral long alkyl chain appended 1,2,3-triazolium ionic liquids
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The increasing importance of ionic liquids (ILs) in various strata of chemical sciences is largely due to the fact that modification in the architecture of the cation and/or the anion imparts favorable and specific properties to an IL. Consequently, there is a need to develop new ILs with different functionalities. A series of l-valine based alkyl chain-appended 1,2,3-triazolium ILs (alkyl = hexyl, octyl, dodecyl, cetyl and octadecyl) with iodide and hexafluorophosphate anions, respectively, are synthesized and characterized. These new ILs show optical activity and hence are termed chiral ILs (CILs). All ten CILs are room temperature ILs (RTILs) as their melting points, obtained from differential scanning calorimetry (DSC), are found to be below ambient temperature. Thermogravimetric analysis indicates these CILs to have adequate thermal stability. The longer alkyl chain containing CILs exhibit facile self-aggregation when dissolved in ethanol. There is a hint of pre-micellar aggregation by short alkyl chain possessing CILs along with the long alkyl chain containing ones. These CILs demonstrate weak absorbance and emission of UV-Vis radiation and hence can be considered ideal solvents for photochemical applications. These CILs, consisting of different functionalities, possess interesting properties and have potential to be used in many areas of chemistry. the Partner Organisations 2014.
- Mishra, Roli,Pandey, Shubha,Trivedi, Shruti,Pandey, Siddharth,Pandey, Pramod S.
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- Step-by-Step Layer-by-Layer Assembly Using 1,2,3-Triazole as a Platform for Controlled Multicharged and Multifunctional Coatings
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Reported for the first time is the use of click chemistry to make layer-by-layer multiple post-functionalization treatments. The use of triazole as a platform for the post-functionalization allows the introduction of new clickable structures on the surface. The layer-by-layer strategy by means of click chemistry allows the introduction of both multiple and/or different consecutive modifications on the surface and multicharged species. Herein it consists of the use of molecules functionalized by a 1-azido group and propargyl bromide to deposit functionalized triazolium-type charged oligomers on the substrate. Moreover, different functional groups can be introduced at each step, which amplifies the use of this strategy for many potential applications. Here, to give an example of applications, that strategy is used to introduce alkyl chains and obtain highly hydrophobic materials. Moreover, it is shown that the surface morphology can also change after each treatment.
- Godeau, Guilhem,Darmanin, Thierry,Guittard, Frédéric
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- Mesogenic copper(II) complexes with [1,2,3]-triazole-based bidentate Schiff bases
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The first mesogenic Cu(II) complex with [1,2,3]-triazole-based bidentate Schiff bases with flexible terminal alkyl chain, CnH2n+1 (even parity of n = 10-18) has been successfully synthesized. The heterocyclic triazole core was introd
- Yeap, Guan-Yeow,Heng, Boon-Teck
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- Antioxidant and Antibacterial Activities of Dodecyl Tannin Derivative Linked with 1,2,3-Triazole
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Dodecyl tannin derivative linked with 1,2,3-triazole was prepared by the click reaction of dodecyl azide and alkynylated tannin. The structure of tannin derivative was identified by FT-IR spectrometer and elemental analyzer, and the surface activity, antioxidant activity and antimicrobial activity of tannin derivative were studied. The surface tension of tannin derivative was significantly reduced because of the introduction of long chain alkyl groups, and the lowest surface tension was 38.87 mN/m at 1.0 mg/mL. The tannin derivative had strong ability to scavenge 1,1-diphenyl-2-picrylhydrazyl radical, the scavenging rate could reach 89.08 % at 0.25 mg/mL. The tannin derivative exhibited strong antibacterial activity against E. coli and S. aureus due to the increased fat-solubility of tannin derivative and the introduction of antibacterial triazole groups in molecular structure of tannin derivative, and the bacteriostatic ratios of tannin derivative against E. coli and S. aureus were 92.16 % and 89.21 % at 2.0 mg/mL, respectively. The tannin derivative can be used as good candidates for antibacterial packaging or antioxidant supplements.
- Yuan, Hua,Zhou, Peng,Peng, Zhiyuan,Wang, Chengzhang
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- Synthesis, surface properties and bioactivity of novel 4-Substituted 1,2,3-Triazole quaternary ammonium surfactants
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Series of novel 1,2,3-triazole based quaternary ammonium surfactants with different hydrophobic chain length and head group substituents were synthetized and characterized. Their surface properties and aggregation behavior were discussed on the basis of tensiometry and conductimetry measurements by using several parameters, including critical micelle concentration (CMC), surface tension at the cmc (γcmc), adsorption efficiency (pC20), effectiveness of surface tension reduction (Πcmc), minimum surface area occupied by a molecule (Amin) at the air ? water interface and standard Gibbs free energy of micellization ΔGMic0. These heterocyclic surfactants exhibit much lower CMC values as compared with those reported for conventional alkyltriethyl ammoniums and alkylbenzyldiethyl ammonium salts. Their micelles formation and surface adsorption in aqueous media can be tuned out through a suitable choice of the substituent attached to the polar head. Triethyl ammonium (CnTzTEA] and diethylbenzyl ammonium surfactants (CnTzBz) showed improved micellization behavior than tetradecyl diethyl ammonium (CnTzC14) homologous. The in vitro antimicrobial activity of the surfactants against B. subtilis, P. aerugenosa and A.niger strains was also investigated. CnTzBz series possessing benzyl chain showed better activity against all the tested microorganisms with minimum inhibitory concentration ranging from 6 to 57 μmol/L.
- Mechken, Karima Amel,Menouar, Mohammed,Belkhodja, Moulay,Saidi-Besbes, Salima
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- ENVIRONMENTALLY-FRIENDLY HYDROAZIDATION OF OLEFINS
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The present invention provides processes for the synthesis of organic azides, intermediates for the production thereof, and compositions related thereto.
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Page/Page column 62-66; 95
(2020/01/24)
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- Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins
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We herein report a direct intermolecular anti-Markovnikov hydroazidation method for unactivated olefins, which is promoted by a catalytic amount of bench-stable benziodoxole at ambient temperature. This method facilitates previously difficult, direct addition of hydrazoic acid across a wide variety of unactivated olefins in both complex molecules and unfunctionalized commodity chemicals. It conveniently fills a synthetic chemistry gap of existing olefin hydroazidation procedures, and thereby provides a valuable tool for azido-group labeling in organic synthesis and chemical biology studies.
- Li, Hongze,Shen, Shou-Jie,Zhu, Cheng-Liang,Xu, Hao
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supporting information
p. 9415 - 9421
(2019/06/21)
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- Fluorinated triazole-containing sphingosine analogues. Syntheses and in vitro evaluation as SPHK inhibitors
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Sphingosine analogues with a rigid triazole moiety in the aliphatic chain and systematic modifications in the polar head and different degrees of fluorination at the terminus of the alkylic chain were synthesized from a common alkynyl aziridine key synthon. This key synthon was obtained by enantioselective organocatalyzed aziridination and it was subsequently ring opened in a regioselective manner in acidic medium. Up to 16 sphingosine analogues were prepared in a straightforward manner. The in vitro activity of the obtained products as SPHK1 and SPHK2 inhibitors was evaluated, displaying comparable activity to that of DMS.
- Escudero-Casao, Margarita,Cardona, Adrià,Beltrán-Debón, Raúl,Díaz, Yolanda,Matheu, M. Isabel,Castillón, Sergio
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supporting information
p. 7230 - 7235
(2018/10/24)
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- Structure-based design of bacterial transglycosylase inhibitors incorporating biphenyl, amine linker and 2-alkoxy-3-phosphorylpropanoate moieties
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Transglycosylase (TGase) is essential to biosynthesis of peptidoglycan for formation of bacterial cell wall. Moenomycin is a potent TGase inhibitor, but not used in clinic treatment due to its poor pharmacokinetics. The E?F disaccharide, phosphoglycerate and lipid tail in moenomycin are crucial elements for TGase inhibition and antibacterial activity. Based on this scaffold, a series of truncated mimics comprising biphenyl, amine linker and 2-alkoxy-3-phosphorylpropanoate moieties were designed to test their TGase inhibitory activity. In this design, the phosphorylpropanoate group is a surrogate of phosphoglycerate with improved stability. A library of lipid tails can be constructed by a straightforward approach using Cu(I)-catalyzed (3 + 2) cycloaddition reactions, and the as-synthesized triazole ring can provide additional hydrogen bonds in the TGase active site. Our molecular docking experiments reveal that the biphenyl group provides π–π and π–cation interactions to act as a simplified alternative of the C–E disaccharide in moenomycin. To play the role of the oxonium transition state in transglycosylation, the amine linker exists as a positively charged species in physiological condition to attain electrostatic interactions with acidic residues. In this study, two biphenyl-linked 2-alkoxy-3-phosphorylpropanoate compounds (8 and 10) are found to exhibit modest inhibitory activity (IC50 ≈ 150 μM) against the TGase of Acinetobacter baumannii and good antibacterial activity against Staphylococcus aureus (MIC = 6.3 μM).
- Yu, Jui-Yin,Cheng, Hsiu-Jung,Wu, Huei-Ru,Wu, Wei-Shen,Lu, Jui-Wen,Cheng, Ting-Jen,Wu, Ying-Ta,Fang, Jim-Min
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p. 729 - 741
(2018/03/26)
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- Silver-mediated oxidative functionalization of alkylsilanes
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A general approach to the functionalization of aliphatic C-Si bonds in the presence of silver salts and oxidants has been reported. This strategy encompasses a range of valuable C-Si transformations, including the direct conversions of a C-Si bond to C-OCF3, C-OBz, C-OCOCF3, C-SCF3, C-SCN, and C-N3 bonds. Among them, trifluoromethoxylation of alkylsilanes is reported for the first time. In addition, mechanistic studies indicate that this reaction may proceed through a radical mechanism.
- Wang, Feng,Xu, Peng,Cong, Fei,Tang, Pingping
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p. 8836 - 8841
(2019/01/03)
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- Chiral induction, transfer and modulation in C 3-symmetric columnar liquid crystalline assemblies
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Circularly polarized light (CPL), regarded as a true chiral entity, has been suggested as one possible origin of homochirality in nature. It still remains difficult to understand the exact mechanism of chiral induction, transfer and amplification in supramolecular assemblies. Herein, we designed and synthesized three discotic diacetylene LC monomers, in which the peripheral diacetylene flexible chains linked to the triazole derivative cores through H-bonding or covalent bonds. We established links between the primary chemical structures of discotic diacetylene monomers, liquid crystal phase structures and optically active properties in the final supramolecular assemblies. Moreover, the type of junction bonding interaction exhibited a significant influence on the chiral transfer in a supramolecular columnar LC system.
- Hu, Jingang,Zhu, Tianyi,He, Chenlu,Zhang, Yan,Zhang, Qijin,Zou, Gang
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supporting information
p. 5135 - 5142
(2017/07/10)
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- The Cu(i)-catalysed Huisgen 1,3-dipolar cycloaddition route to (bio-)organic functionalisation of polyoxovanadates
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The [V6O13{(OCH2)3CCH2OCH2CCH}2]2- with two terminal alkyne functionalities exhibits excellent reactivity towards (bio-)organic azides. The designed synthetic protocol for the generation of triazol-modified Lindqvist hexavanadates grants access to bio-"clicked" polyoxometalates with spectroscopically detectable 51V nuclei.
- Linnenberg, Oliver,Kondinski, Aleksandar,St?cker, Cornelia,Monakhov, Kirill Yu.
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supporting information
p. 15636 - 15640
(2017/12/02)
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- Promise of Retinoic Acid-Triazolyl Derivatives in Promoting Differentiation of Neuroblastoma Cells
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Retinoic acid induces differentiation in various types of cells including skeletal myoblasts and neuroblasts and maintains differentiation of epithelial cells. The present study demonstrates synthesis and screening of a library of retinoic acid-triazolyl derivatives for their differentiation potential on neuroblastoma cells. Click chemistry approach using copper(I)-catalyzed azide-alkyne cycloaddition was adopted for the preparation of these derivatives. The neurite outgrowth promoting potential of retinoic acid-triazolyl derivatives was studied on neuroblastoma cells. Morphological examination revealed that compounds 8a, 8e, 8f, and 8k, among the various derivatives screened, exhibited promising neurite-outgrowth inducing activity at a concentration of 10 μM compared to undifferentiated and retinoic acid treated cells. Further on, to confirm this differentiation potential of these compounds, neuroblastoma cells were probed for expression of neuronal markers such as NF-H and NeuN. The results revealed a marked increase in the NF-H and NeuN protein expression when treated with 8a, 8e, 8f, and 8k compared to undifferentiated and retinoic acid treated cells. Thus, these compounds could act as potential leads in inducing neuronal differentiation for future studies. (Chemical Equation Presented).
- Lone, Ali Mohd,Dar, Nawab John,Hamid, Abid,Shah, Wajaht Amin,Ahmad, Muzamil,Bhat, Bilal A.
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- Asymmetrical azobenzene liquid crystals with high birefringence prepared via click chemistry
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Asymmetrical azobenzene liquid crystals with high birefringence were prepared via the click chemistry method. The chemical structures of the synthetic intermediates and compounds were confirmed by FT-IR and 1H-NMR. The liquid crystal behavior,
- Miao, Zongcheng,Zhang, Yongming,Zhao, Yuzhen,Wang, Zhixue,Wang, Dong
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- Water soluble octa-functionalized POSS: All-click chemistry synthesis and efficient host-guest encapsulation
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A series of water soluble octa-functionalized POSSs were facilely synthesized via thiol-ene and Menschutkin click chemistry. Among them, octa-alkynyl POSS further reacted with azide-terminal alkyl long chains, resulting in a well-defined, amphiphilic octopus-like POSS. For the first time it was used for host-guest encapsulation and it exhibited an ultrahigh loading capability.
- Han, Jin,Zheng, Yaochen,Zheng, Shuai,Li, Sipei,Hu, Tiannan,Tang, Aijin,Gao, Chao
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supporting information
p. 8712 - 8714
(2014/07/22)
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- Mesogenic copper(II) complexes with [1,2,3]-triazole-based bidentate Schiff bases
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The first mesogenic Cu(II) complex with [1,2,3]-triazole-based bidentate Schiff bases with flexible terminal alkyl chain, CnH2n + 1 (even parity of n = 10-18) has been successfully synthesized. The heterocyclic triazole core was intr
- Yeap, Guan-Yeow,Heng, Boon-Teck
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p. 247 - 254
(2016/02/18)
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- Design, synthesis, and characterization of 1,3,5-Tri(1 H-benzo[d]imidazol-2-yl)benzene-based fluorescent supramolecular columnar liquid crystals with a broad mesomorphic range
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A new kind of supramolecular columnar liquid crystal T-A with a broad mesomorphic range (up to 164.9 °C), good thermal stability, and strong fluorescence is designed and formed by the H-bonding between 1,3,5-tri(1H-benzo[d]imidazol-2-yl)benzene (T) and serial gallic acid derivatives (A). Two components are easily available because of simple routes, common reactions, high yields, commercial starting materials, and inexpensive catalysts. The introduction of the 1,2,3-triazole structure into component A makes the textures different and is slightly disadvantageous for the T-A complexes.
- Xiong, Jin-Feng,Luo, Shi-He,Huo, Jing-Pei,Liu, Jin-Yan,Chen, Shui-Xia,Wang, Zhao-Yang
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p. 8366 - 8373
(2015/03/18)
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- Chemical synthesis and biological evaluation of triazole derivatives as inhibitors of InhA and antituberculosis agents
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A series of triazoles have been prepared and evaluated as inhibitors of InhA as well as inhibitors of Mycobacterium tuberculosis H37R v. Several of these new compounds possess a good activity against InhA, particularly compounds 17 and 18 for which molecular docking has been performed. Concerning their activities against M. tuberculosis H 37RV strain, two of them, 3 and 12, were found to be good inhibitors with MIC values of 0.50 and 0.25 μg/mL, respectively. Particularly, compound 12 presenting the best MIC value of all compounds tested (0.6 μM) is totally inactive against InhA.
- Menendez, Christophe,Chollet, Aurélien,Rodriguez, Frédéric,Inard, Cyril,Pasca, Maria Rosalia,Lherbet, Christian,Baltas, Michel
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experimental part
p. 275 - 283
(2012/07/30)
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- Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators
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New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists.
- Sabbah, Mohamad,Fontaine, Fanny,Grand, Lucie,Boukraa, Mohamed,Efrit, Mohamed L.,Doutheau, Alain,Soulere, Laurent,Queneau, Yves
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scheme or table
p. 4727 - 4736
(2012/08/29)
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- A practical one-pot synthesis of azides directly from alcohols
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Alkyl/benzyl azides can be readily synthesized in excellent yields from their corresponding alcohols by stirring a solution of sodium azide in DMSO with a thoroughly ground equimolecular mixture of triphenylphosphine, iodine and imidazole. Indian Academy
- Rokhum, Lalthazuala,Bez, Ghanashyam
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experimental part
p. 687 - 691
(2012/08/07)
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- A radical procedure for the anti-markovnikov hydroazidation of alkenes
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A one-pot procedure for the efficient hydroazidation of alkenes involving hydroboration with catecholborane followed by reaction with benzenesulfonyl azide in the presence of a radical initiator is described. The regioselectivity is controlled by the hydroboration step and corresponds in most cases to an anti-Markovnikov regioselectivity. This procedure is applicable to a wide range of alkenes and gives excellent results with 1,2-disubstituted and trisubstituted alkenes.
- Kapat, Ajoy,Koenig, Andreas,Montermini, Florian,Renaud, Philippe
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supporting information; experimental part
p. 13890 - 13893
(2011/10/31)
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- Complementary hydrogen bonding between a clicked C3-symmetric triazole derivative and carboxylic acids for columnar liquid-crystalline assemblies
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Two's complement: A series of discotic hydrogen-bonded complexes was prepared from a "clicked" triazole derivative with C3 symmetry and carboxylic acids (see picture; R1, R2=alkyl groups). Owing to the extended rigid core
- Ryu, Mi-Hee,Choi, Jin-Woo,Kim, Ho-Joong,Park, Noejung,Cho, Byoung-Ki
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supporting information; experimental part
p. 5737 - 5740
(2011/08/06)
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- Synthesis of novel D-glucose-derived benzyl and alkyl 1,2,3-triazoles as potential antifungal and antibacterial Agents
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A series of novel glucose derived benzyl and alkyl 1,2,3-triazoles and their hydrochlorides have been synthesized via Cu(I)-catalyzed 1,3-dipolar cycloaddition. All the new compounds were characterized by MS, IR and NMR spectra. The DEPT, APT, 1/sup
- Wei, Jin-Jian,Jin, Lei,Wan, Kun,Zhou, Cheng-He
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scheme or table
p. 229 - 238
(2011/12/01)
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- Synthesis and biological activities of triazole derivatives as inhibitors of InhA and antituberculosis agents
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InhA, the enoyl reductase from the mycobacterial type II fatty acid biosynthesis pathway, is a target for the development of novel drugs against tuberculosis. We exploited copper-catalyzed [3+2] cycloaddition between alkynes and different azides to afford 1,4-disubstituted triazole or α-ketotriazole derivatives. Several compounds bearing a lipophilic chain mimicking the substrate were able to inhibit InhA. Among them, 1-dodecyl-4-phenethyl-1H-1,2,3-triazole displayed a minimum inhibitory concentration inferior to 2 μg/mL against Mycobacterium tuberculosis H37Rv.
- Menendez, Christophe,Gau, Sylvain,Lherbet, Christian,Rodriguez, Frédéric,Inard, Cyril,Pasca, Maria Rosalia,Baltas, Michel
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experimental part
p. 5524 - 5531
(2011/12/15)
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- Unsupported copper nanoparticles in the 1,3-dipolar cycloaddition of terminal alkynes and azides
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Readily prepared copper nanoparticles were found to catalyse the 1,3-dipolar cycloaddition of azides and alkynes up to rates comparable to those of microwave chemistry. Both the preparation of the nanoparticles and the click reaction are carried out under mild conditions, in short reaction times and in the absence of any stabilising additive or ligand. A variety of 1,2,3-triazoles were prepared in excellent yields. A reaction mechanism was postulated on the basis of different reactivity studies and deuteration experiments. Copper(I) acetylides were demonstrated to be the real intermediate species.
- Alonso, Francisco,Moglie, Yanina,Radivoy, Gabriel,Yus, Miguel
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supporting information; experimental part
p. 1875 - 1884
(2010/07/18)
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- Click chemistry approach to new N-substituted aminocyclitols as potential pharmacological chaperones for gaucher disease
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New N-alkylaminocyclitols bearing a 1,2,3-triazole system at different positions of the alkyl chain have been prepared as potential GCase pharmacological chaperones using click chemistry approaches. Among them, compounds 1d and 1e, with the shorter spacer
- Díaz, Lucía,Bujons, Jordi,Casas, Josefina,Llebaria, Amadeu,Delgado, Antonio
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supporting information; experimental part
p. 5248 - 5255
(2010/10/19)
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- Synthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities
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A series of novel sulfanilamide-derived 1,2,3-triazole compounds were synthesized in excellent yields via 1,3-dipolar cycloaddition and confirmed by MS, IR and NMR spectra as well as elemental analyses. All the compounds were screened in vitro for their antibacterial and antifungal activities. Preliminary results indicated that some target compounds exhibited promising antibacterial potency. Especially, 4-amino-N-((1-dodecyl-1H-1,2,3-triazol-4-yl)methyl) benzenesulfonamide, N-((1-(2,4-dichlorobenzyl)- 1H-1,2,3-triazol-4-yl)methyl)-4- aminobenzenesulfonamide and 4-amino-N-((1-(2,4-difluorobenzyl)- 1H-1,2,3-triazol-4-yl)methyl) benzenesulfonamide were found to be the most potent compounds against all the tested strains except for Candida albicans (ATCC76615) and Candida mycoderma.
- Wang, Xian-Long,Wan, Kun,Zhou, Cheng-He
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experimental part
p. 4631 - 4639
(2010/10/19)
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- A novel modular approach to triazole-functionalized phthalocyanines using click chemistry
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(Chemical Equation Presented) A novel, elegant, and significantly improved protocol for the synthesis of a protected octaacetylene phthalocyanine is described. Inexpensive, mild, and environmentally benign iodination of 1,2-dibromobenzene and subsequent optimized chemoselective palladium-catalyzed cyanation are employed to effectively build up the key intermediate 4,5-dibromophthalonitrile in two steps. Introduction of the tert- butyldimethylsilyl-protected acetylene moieties via a Sonogashira cross-coupling provides the desired phthalonitrile precursor that, after cyclization, yielded the protected octaacetylene phthalocyanine. Subsequently, in situ deprotection and "clicking" are employed as a highly efficient and quantitative route to a novel class of octatriazole-functionalized phthalocyanines. The ability of such triazole-derived phthalocyanines to form well-defined supramolecular structures upon doping with zinc(II) triflate is demonstrated.
- Jurí?ek, Michal,Kouwer, Paul H. J.,Rehák, Juraj,Sly, Joseph,Rowan, Alan E.
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supporting information; experimental part
p. 21 - 25
(2009/04/07)
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- Remarkable high-yielding chemical modification of gold nanoparticles using uncatalyzed click-type i ,3-dipolar cycloaddition chemistry and hyperbaric conditions
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Azide-terminated alkyl thiolate monolayer-protected gold nanoparticles (1-C,12MPN) with a core size of 1.8 ± 0.2 nm were prepared. 1-C,12MPN was modified in high yields via an uncatalyzed 1,3-dipolar cycloaddition (clicktype reaction) with a variety of terminal acyl alkynes under hyperbaric conditions at 11 000 atm. The resulting 1,2,3-tria- zole modified MPNs (2-C,12MPN) were characterized using 1H NMR spectroscopy and were verified by comparison of the spectra to those obtained for the products of the model reactions of 1-azidododecane with the same alkynes. TEM analysis showed that the high-pressure conditions did not affect the size of the gold core, suggesting that the only effect is to facilitate the chemical reaction on the particles.
- Ismaili, Hossein,Alizadeh, Abdoihamid,Snell, Kristen E.,Workentin, Mark S.
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experimental part
p. 1708 - 1715
(2010/01/29)
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- A simple and convenient synthesis of alkyl azides under mild conditions
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Various primary and secondary alkyl azides have been synthesized in high yields by the fluoride anion induced S(N)2 substitution reactions of the corresponding alkyl halides, phosphates, or tosylates and trimethylsilyl azide.
- Ito,Koyakumaru,Ohta,Takaya
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p. 376 - 378
(2007/10/02)
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- Oxidatively Assisted Alkylation of Sodium Nitrocyanamide and Sodium Azide
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m-Chloroperbenzoic acid (MCPBA) oxidatively assisted reactions at 25 deg C between straight chain primary alkyl iodides and sodium nitrocyanamide to give corresponding alkyl nitrocyanamides (N-alkylation) and N-alkoxy-N'-cyanodiazene N-oxides (O-alkylation).Each alkyl nitrocyanamide thermolysed to an alkyl isocyanate.In the absence of oxidative assistance sodium nitrocyanamide suspended in an inert solvent (25 deg C to 110 deg C) did not convert straight chain primary alkyl halides.Simple secondary and tertiary alkyl iodides and isobutyl iodide in the presence of MCPBA and sodium nitrocyanamide were converted to intractable mixtures that did not contain detectable amounts of alkyl nitrocyanamides, isocyanates, or N-alkoxy-N'-cyanodiazene N-oxides.This differential reactivity between the various types of alkyl iodides was supported by a similar conversion of straight chain primary alkyl iodides to corresponding azides and other alkyl iodides to intractable mixtures on treatment with sodium azide under conditions that brought about no reaction in the absence of oxidative assistance of MCPBA.Alkyl iodides were unreactive (25 deg C to 110 deg C) to sodium cyanate in the presence or absence of peroxides.
- Manimaran, Thanikavelu,Wolford, Lionel T.,Boyer, Joseph H.
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p. 2525 - 2532
(2007/10/02)
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