- Effect of 1,2,3-triazole salts, non-classical bioisosteres of miltefosine, on Leishmania amazonensis
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Here, we report the effect of new non-classical bioisosteres of miltefosine on Leishmania amazonensis. Fifteen compounds were synthesized and the compound dhmtAc, containing an acetate anion, a side chain of 10 carbon atoms linked to N-1 and a methyl group linked to N-3, showed high and selective biological activity against L. amazonensis. On the intracellular amastigotes, stages of the parasite related to human disease, the IC50 values were near or similar to the 1.0?μM (0.9, 0.8 and 1.0?μM on L. amazonensis-WT, and two transgenic L. amazonensis expressing GFP and RFP, respectively), being more active than miltefosine. Furthermore, dhmtAc did not show toxic effects on human erythrocytes and macrophages (CC50?=?115.9?μM) being more destructive to the intracellular parasites (selectivity index?>?115). Promastigotes and intramacrophage amastigotes treated with dhmtAc showed low capacity for reversion of the effect of the compound. A study of the mechanism of action of this compound showed some features of metazoan apoptosis, including cell volume decreases, loss of mitochondrial membrane potential, ROS production, an increase in the intracellular lipid bodies, in situ labeling of DNA fragments by TUNEL labeling and phosphatidylserine exposure to the outerleaflet of the plasma membrane. In addition, the plasma membrane disruption, revealed by PI labeling, suggests cell death by necrosis. No increase in autophagic vacuoles formation in treated promastigotes was observed. Taken together, the data indicate that the bioisostere of miltefosine, dhmtAc, has promising antileishmanial activity that is mediated via apoptosis and necrosis.
- Stroppa, Pedro H.F.,Antinarelli, Luciana M.R.,Carmo, Arturene M.L.,Gameiro, Jacy,Coimbra, Elaine S.,da Silva, Adilson D.
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- Thermochemistry of organic azides revisited Dedicated to Prof. Ch. Rüchardt on the Occasion of His 85th Birthday
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Highly pure samples of 4-nitro-phenyl azide, 1-octyl azide and 1 decyl-azide were prepared for thermochemical studies. Vapour pressures over the solid and the liquid sample of 4-nitro-phenyl azide have been determined by the transpiration method. The molar enthalpies of vaporization/sublimation for this compound were derived from the temperature dependencies of vapour pressures. The molar enthalpy of fusion of 4-nitro-phenyl azide was measured by DSC. The measured data set for 4-nitro-phenyl azide was successfully checked for internal consistency. Molar enthalpies of vaporization of 1-octyl azide and 1 decyl-azide were measured by transpiration. The molar enthalpies of formation of the liquid 1-octyl azide and 1 decyl-azides were derived from the combustion calorimetry. New experimental results for these organic azides have been used to derive their molar enthalpies of formation in the gas state and for comparison with results from quantum-chemical method G4.
- Emel'Yanenko, Vladimir N.,Algarra, Manuel,Esteves Da Silva, Joaquim C.G.,Hierrezuelo, Jesús,López-Romero, Juan M.,Verevkin, Sergey P.
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- Antitubercular activity of 1,2,3-triazolyl fatty acid derivatives
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A collection of 1,2,3-triazoles unsaturated fatty acid mimics were efficiently synthesized by click chemistry. The 1,4-disubstituted analogs prepared covered different alkyl chain lengths and triazole positions. The compounds were subsequently tested against Mycobacterium tuberculosis, being most of them active with some of the analogs displaying activity at micromolar concentration. The most potent member of the series has the triazole moiety on the C-2 position with a carbon chain of eight or ten carbon atoms. The 1,5-isomers of the most active analog were significantly less active than the original isomer. The activity of the selected hit was assayed on several clinical MTB multi-drug resistant strains providing the same MIC.
- Ghiano, Diego G.,de la Iglesia, Agustina,Liu, Nina,Tonge, Peter J.,Morbidoni, Héctor R.,Labadie, Guillermo R.
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- Adding diversity to ruthenium(II)-arene anticancer (RAPTA) compounds via click chemistry: The influence of hydrophobic chains
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The application of click chemistry to develop libraries of organometallic ruthenium-arene complexes with potential anticancer properties has been investigated. A series of ruthenium-imidazole-triazole complexes, with hydrophobic tails, were prepared from a common precursor via click chemistry. The tail could be attached to the ligand prior to coordination to the ruthenium complex or following coordination, the former giving the product in superior yield. The complexes were screened for cytotoxicity in tumourigenic and non-tumourigenic cell lines, and while the compounds were only moderately cytotoxic, good selectivity for tumourigenic cells was observed.
- Renfrew, Anna K.,Juillerat-Jeanneret, Lucienne,Dyson, Paul J.
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- Synthesis of new chrysin derivatives with substantial antibiofilm activity
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Abstract: Multidrug resistance mechanism of microorganisms towards conventional antimicrobials nowadays faces a common health problem. So, searching and development of new antibacterials are in the frontier areas of biochemistry. Functionalizations of various natural products or synthesis of compounds through molecular modeling followed by virtual screening are the ways to obtain potential leads. Chrysin is one of the plant secondary metabolites and is ubiquitously present in majority of plants. It has multi-dimensional potentiality however, with a very low bioavailability causing a very low efficacy. Very few chrysin derivatives possessing antimicrobial activity with a low anti-biofilm efficacy have been found in the literature. Thus, it has been attempted to synthesize a series of new chrysin derivatives (CDs). In this study, twenty-two new derivatives have been synthesized via its 7-OH modulation and antibiofilm activity was evaluated against a model bacterium viz. Escherichia coli MTCC 40 (Gram negative). Eleven CDs coded as 2a, 2b, 2c, 2e, 2f, 2g, 2h, 2i, 3j, 3k and 3l have been found more potent compared to chrysin (precursor of CDs) against planktonic form of E. coli. Biofilm inhibition studies indicated a noteworthy results for 2a (93.57%), 2b (92.14%), 2f (92.14%) and 3l (93.57%) compared to chrysin (33.57%). E. coli motility was also highly restricted by 2a, 2b, 2f and 3l than chrysin at their sub-inhibitory concentrations. Solubility studies indicated an extended-release of 2a, 2b, 2f and 3l in physiological systems. Relatively higher bioavailability of 2a, 2b, 2f and 3l than chrysin was revealed from the dissolution experiments and was further validated through in silico ADME-based SAR analysis. Hence, this study is more interesting in regard to antibacterial potentiality of chrysin derivatives against Escherichia coli MTCC 40 (Gram negative). Thus, this article might be useful for further design and development of new leads in the context of biofilm-associated bacterial infections. Graphic abstract: [Figure not available: see fulltext.].
- Akhter, Yusuf,Anand, Pragya,Bhowmik, Sukhen,Das, Manash C.,Das, Riyanki,De, Utpal C.,Sen, Tirtharaj
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p. 137 - 156
(2022/03/09)
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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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- Room temperature perylene based columnar liquid crystals as solid-state fluorescent emitters in solution-processable organic light-emitting diodes
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The finding of pure organic emitter materials is the need of the hour for the mass production of cost-effective and metal-free fluorescent organic light-emitting diodes (FOLEDs). In this paper, we report a new series of perylene tetraesters (PTEs) that exhibit the room temperature columnar (Col) mesophase and can act as efficient fluorescent emitter materials in OLEDs. The molecular design involves the attachment of triazole moieties with the PTE discotic coreviaclick chemistry. Triazole groups were chosen as they can improve the electron transport as well as tune the luminescence behavior of discogens. All the PTE derivatives3a-dexhibited ordered columnar rectangular (Colro) mesophases at ambient temperatures suitable for various device applications. The electron mobility of perylene tetraester derivative3awas measured in the mesophase by time of flight (TOF) technique and found to be 0.014 cm2V?1s?1. However, the balanced hole and electron charge transport behaviour was observed in fabricated hole-only and electron-only devices. Taking advantage of both charge transport and the luminescence nature of the PTE derivative in OLEDs, a series of devices were fabricated by utilizing3aas a sole emitter and in the dispersed form at 1, 5 and 8 wt% with the CBP host and at 5 wt% in the SimCP2 host. A significantly high value of the external quantum efficiency (EQE) of 6.5% is obtained in doped devices with the CBP host at 5 wt% dopant (3a) concentration with CIE coordinates of (0.37, 0.53) corresponding to green color. The obtained high EQE value will certainly offer an important step forward to expand the application of smart DLC materials in OLEDs.
- Bala, Indu,De, Joydip,Douali, Redouane,Dubey, Deepak Kumar,Gupta, Santosh Prasad,Jou, Jwo-Huei,Pal, Santanu Kumar,Singh, Dharmendra Pratap,Singh, Nitya,Yadav, Rohit Ashok Kumar
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supporting information
p. 12485 - 12494
(2020/10/06)
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- Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,2,3-Triazole-5-carboxamides Using Dimethyl Carbonate as Sustainable Solvent
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A simple and direct palladium-catalyzed aminocarbonylation of 5-iodo-1,2,3-triazoles backbone for the incorporation of an amide functional group is presented. The approach is based on the palladium catalyzed carbonylative coupling reaction of iodo-triazole with different amines employing formic acid and sulfuric acid as CO source (Morgan's reaction) to provide the 1,2,3-triazole-5-carboxamides in good to excellent yields. The important features of this methodology include short reaction time, high yields, the use of dimethyl carbonate as a sustainable solvent, and the use of efficient alternative source of carbon monoxide, avoiding pressurized cylinder. The methodology described herein for the synthesis of 1,4,5-trisubstituted 1,2,3-triazole-5-carboxamides, can offers an alternative path for functionalization of other heterocycles.
- de Albuquerque, Danilo Yano,de Moraes, Juliana R.,Schwab, Ricardo S.
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supporting information
p. 6673 - 6681
(2019/11/02)
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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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- NCN-Coordinating Ligands based on Pyrene Structure with Potential Application in Organic Electronics
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Five novel derivatives of pyrene, substituted at positions 1,3,6,8 with 4-(2,2-dimethylpropyloxy)pyridine (P1), 4-decyloxypyridine (P2), 4-pentylpyridine (P3), 1-decyl-1,2,3-triazole (P4), and 1-benzyl-1,2,3-triazole (P5), are obtained through a Suzuki–Miyaura cross-coupling reaction or CuI-catalyzed 1,3-dipolar cycloaddition reaction, respectively, and characterized thoroughly. TGA measurements reveal the high thermal stability of the compounds. Pyrene derivatives P1–P5 all show photoluminescence (PL) quantum yields (Φ) of approximately 75 % in solution. Solid-state photo- and electroluminescence characteristics of selected compounds as organic light-emitting diodes are tested. In the guest–host configuration, two matrixes, that is, poly(N-vinylcarbazole) (PVK) and a binary matrix consisting of PVK and 2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PBD) (50:50 wt %), are applied. The diodes show red, green, or blue electroluminescence, depending on both the compound chemical structure and the actual device architecture. In addition, theoretical studies (DFT and TD-DFT) provide a deeper understanding of the experimental results.
- Zych, Dawid,Kurpanik, Aneta,Slodek, Aneta,Maroń, Anna,Paj?k, Micha?,Szafraniec-Gorol, Gra?yna,Matussek, Marek,Krompiec, Stanis?aw,Schab-Balcerzak, Ewa,Kotowicz, Sonia,Siwy, Mariola,Smolarek, Karolina,Ma?kowski, Sebastian,Danikiewicz, Witold
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supporting information
p. 15746 - 15758
(2017/10/23)
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- Efficient click chemistry towards fatty acids containing 1,2,3-triazole: Design and synthesis as potential antifungal drugs for Candida albicans
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Candida is an important opportunistic human fungal pathogen. The cis-2-dodecenoic acid (BDSF) showing in vitro activity of against C. albicans growth, germ-tube germination and biofilm formation has been a potential inhibitor for Candida and other fungi.
- Fu, Nina,Wang, Suiliang,Zhang, Yuqian,Zhang, Caixia,Yang, Dongliang,Weng, Lixing,Zhao, Baomin,Wang, Lianhui
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supporting information
p. 596 - 602
(2017/05/29)
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- Designing Simple Lipidated Lysines: Bifurcation Imparts Selective Antibacterial Activity
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In the global effort to thwart antimicrobial resistance, lipopeptides are an important class of antimicrobial agents, especially against Gram-negative infections. In an attempt to circumvent their synthetic complexities, we designed simple membrane-active agents involving only one amino acid and two lipid tails. Herein we show that the use of two short lipid tails instead of a single long one significantly increases selective antibacterial activity. This study yielded several selective antibacterial compounds, and investigations into the properties of this compound class were conducted with the most active compound. Fluorescence spectroscopic studies revealed the capacity of the representative compound to cause depolarization and permeabilization of bacterial cell membranes. This membrane-active nature of the compound imparts superior activity against persister cells, biofilms, and planktonic cells. Topical application of the compound decreased bacterial burden in mice inflicted with burn-infections caused by Acinetobacter baumannii. We anticipate that the design principles described herein will direct the development of several antimicrobial agents of clinical importance.
- Ghosh, Chandradhish,Konai, Mohini Mohan,Sarkar, Paramita,Samaddar, Sandip,Haldar, Jayanta
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supporting information
p. 2367 - 2371
(2016/11/13)
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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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p. 206 - 209
(2015/12/30)
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- Triazole substitution of a labile amide bond stabilizes pantothenamides and improves their antiplasmodial potency
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The biosynthesis of coenzyme A (CoA) from pantothenate and the utilization of CoA in essential biochemical pathways represent promising antimalarial drug targets. Pantothenamides, amide derivatives of pantothenate, have potential as antimalarials, but a serum enzyme called pantetheinase degrades pantothenamides, rendering them inactive in vivo. In this study, we characterize a series of 19 compounds that mimic pantothenamides with a stable triazole group instead of the labile amide. Two of these pantothenamides are active against the intraerythrocytic stage parasite with 50% inhibitory concentrations (IC50s) of ~50 nM, and three others have submicromolar IC50s. We show that the compounds target CoA biosynthesis and/or utilization. We investigated one of the compounds for its ability to interact with the Plasmodium falciparum pantothenate kinase, the first enzyme involved in the conversion of pantothenate to CoA, and show that the compound inhibits the phosphorylation of [14C]pantothenate by the P. falciparum pantothenate kinase, but the inhibition does not correlate with antiplasmodial activity. Furthermore, the compounds are not toxic to human cells and, importantly, are not degraded by pantetheinase.
- Howieson, Vanessa M.,Tran, Elisa,Hoegl, Annabelle,Fam, Han Ling,Fu, Jonathan,Sivonen, Kate,Li, Xiao Xuan,Auclair, Karine,Saliba, Kevin J.
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p. 7146 - 7152
(2016/11/28)
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- Synthesis of novel 1-substituted triazole linked 1,2-benzothiazine 1,1-dioxido propenone derivatives as potent anti-inflammatory agents and inhibitors of monocyte-to-macrophage differentiation
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A series of novel 1-substituted-triazole linked 1,2-benzothiazine 1,1-dioxido propenone derivatives 8a-s & 12a-l were prepared from 1-substituted 1,2,3-triazol-4-aldehydes 6 & 11 with N-methyl-3-acetyl-4-hydroxybenzothiazine-1,1-dioxide 7 by condensation.
- Gannarapu, Malla Reddy,Vasamsetti, Sathish Babu,Punna, Nagender,Kotamraju, Srigiridhar,Banda, Narsaiah
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supporting information
p. 1494 - 1500
(2015/08/18)
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- Diversity oriented synthesis of novel haloglycolipids potentially useful for crystallization of integral membrane proteins
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A series of novel haloglycolipids were synthesized based on Cu(i) catalyzed Huisgen's [3 + 2] cycloaddition reaction of diversely functionalized azides and alkynes, using a mixture of N-bromosuccinimide and Cu(i) halide as the halogen source. Since halogen atoms, like bromine and iodine, with a very high scattering power facilitate the solving of crystal structures, the title haloglycolipids could prove to be invaluable in structure-based drug design involving membrane proteins as targets. This journal is the Partner Organisations 2014.
- Sahoo, Laxminarayan,Singhamahapatra, Anadi,Loganathan, Duraikkannu
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p. 2615 - 2625
(2014/04/17)
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- One-pot synthesis of Au@SiO2 catalysts: A click chemistry approach
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Using the copper-catalyzed azide-alkyne cycloaddition "click" reaction, a library of triazole amphiphiles with a variety of functional polar "heads" and hydrophobic or superhydrophobic "tails" was synthesized. The amphiphiles were evaluated for their abil
- Solovyeva, Vera A.,Vu, Khanh B.,Merican, Zulkifli,Sougrat, Rachid,Rodionov, Valentin O.
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supporting information
p. 513 - 517
(2015/01/09)
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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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p. 247 - 254
(2014/04/03)
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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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- Toward analogues of MraY natural inhibitors: Synthesis of 5′-triazole-substituted-aminoribosyl uridines through a Cu-catalyzed azide-alkyne cycloaddition
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A straightforward strategy for the synthesis of triazole-containing MraY inhibitors has been developed. It involves the sequential introduction of a terminal alkyne at the 5′ position of an uridine derivative and O-glycosylation with a protected aminoribose leading to an elaborated alkyne scaffold. An efficient Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) allowed the introduction of chemical diversity toward a small library of inhibitors.
- Fer, Mickael J.,Olatunji, Samir,Bouhss, Ahmed,Calvet-Vitale, Sandrine,Gravier-Pelletier, Christine
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p. 10088 - 10105
(2013/11/06)
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- Long-chain triazolyl acids as inhibitors of osteoclastogenesis
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Saturated fatty acids (e.g., palmitic acid) are known to moderately inhibit the development of osteoclasts in vitro. In pursuit of more effective inhibitors of osteoclastogenesis we explored two new classes of palmitic acid analogues containing either an ether or triazolyl group at various positions along the chain. The compounds were evaluated for their ability to inhibit the formation of osteoclasts in primary mouse bone marrow cultures. The oxyacids were generally prepared by condensation of the appropriate alkyl halides and diols, followed by Jones oxidation. The triazolyl acids were prepared by copper-catalysed click chemistry between alkyl azides and acetylenic acids, or with the appropriately-protected azides and alkynes, followed by deprotection and oxidation. The oxyacids were little more effective than palmitic acid, but the triazolyl analogues were much more effective osteoclastogenesis inhibitors, especially when the triazole was distant from the acid unit.
- Marshall, Andrew J.,Lin, Jian-Ming,Grey, Andrew,Reid, Ian R.,Cornish, Jillian,Denny, William A.
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p. 4112 - 4119
(2013/07/27)
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- Synthesis of novel 2-alkyl triazole-3-alkyl substituted quinoline derivatives and their cytotoxic activity
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The propargyl alcohol on reaction with alkylazides under Sharpless conditions through click chemistry concept gave exclusively 1,4-disubstituted triazoles 2. The compounds 2 were oxidized to aldehydes 3 followed by reaction with aniline resulted Schiff's
- Sambasiva Rao,Kurumurthy,Veeraswamy,Santhosh Kumar,Shanthan Rao,Pamanji,Venkateswara Rao,Narsaiah
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supporting information
p. 1225 - 1227
(2013/03/14)
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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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scheme or table
p. 231 - 235
(2012/05/20)
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- New glucocerebrosidase inhibitors by exploration of chemical diversity of N -substituted aminocyclitols using click chemistry and in situ screening
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A library of aminocyclitols derived from CuAAC reaction between N-propargylaminocyclitol 4 and a series of azides [1′25] is described and tested against GCase. Azides have been chosen from a large collection of potential candidates that has been filtered
- Díaz, Lucía,Casas, Josefina,Bujons, Jordi,Llebaria, Amadeu,Delgado, Antonio
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supporting information; experimental part
p. 2069 - 2079
(2011/06/10)
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- Synthesis of a star polymer library with a diverse range of highly functionalized macromolecular architectures
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An efficient and versatile synthetic route toward highly functionalized core cross-linked star (CCS) polymers with interesting structures and properties is presented using an alkyne CCS polymer as scaffold. The alkyne CCS polymer scaffold was initially prepared via an improved arm-first approach, through ring-opening polymerization (ROP) of 4,4′-bioxepanyl-7,7′-dione (BOD) with a poly(caprolactone-b-propargyl methacrylate) macroinitiator and stannous triflate (Sn(OTf)2) catalyst. Highly functionalized fluorescent, saccharide and amphiphilic CCS polymers were synthesized by grafting the alkyne CCS polymer with the corresponding azido substituted compounds via copper catalyzed 1,3-dipolar azide-alkyne cycloaddition (CuAAC), 'click' chemistry. The resulting corona-functionalized CCS polymers were characterized via GPC, 1H NMR spectroscopic analysis and DLS. 1H NMR spectroscopic analysis revealed that the grafting efficiency (i.e., click efficiency) ranged from 10 to >99% and was highly dependent on the structure and functionality of the azido compounds. This equates to the grafting of 45 to 450 functional compounds onto the CCS polymer scaffolds corona. The results indicate that the click functionalization efficiency is closely related to the molecular size of the azido compounds. Other than size, factors including molecular structure, compatibility and synergistic driving forces, such as the formation of potential inclusion complexes, are also found to affect the functionalization efficiencies.
- Ren, Jing M.,Wiltshire, James T.,Blencowe, Anton,Qiao, Greg G.
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experimental part
p. 3189 - 3202
(2012/03/10)
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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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- Facile synthesis of 4-vinyl- and 4-fluorovinyl-1,2,3-triazoles via bifunctional "click-olefination" reagents
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Modular synthesis of vinyl and fluorovinyl triazoles can be achieved from bifunctional propargyl and fluoropropargyl sulfones by Cu-catalyzed azide-alkyne ligation and Julia-Kocienski olefination. Competitive click reactions of the protio and fluoropropar
- Kumar, Rakesh,Pradhan, Padmanava,Zajc, Barbara
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supporting information; experimental part
p. 3891 - 3893
(2011/05/03)
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- CuAAC macrocyclization: High intramolecular selectivity through the use of copper-tris(triazole) ligand complexes
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A range of multivalent heteroaryl ligands, copper sources, and solvent systems have been investigated for use in CuAAC-mediated macrocyclization reactions. These studies have revealed the key factors governing selectivity for macrocyclization versus dimerization and identified a simple but specific set of reaction conditions capable of efficiently generating a diverse series of drug-like macrocycles at modest dilution in up to 95% yield.
- Chouhan, Gagan,James, Keith
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supporting information; experimental part
p. 2754 - 2757
(2011/06/26)
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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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supporting information; experimental part
p. 6353 - 6356
(2011/12/02)
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- Stabilization of Cu(0)-nanoparticles into the nanopores of modified montmorillonite: An implication on the catalytic approach for "click" reaction between azides and terminal alkynes
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In situ generation of Cu(0)-nanoparticles in the nanopores of modified montmorillonite and their catalytic activity in 1,3-dipolar cycloaddition reactions between azides and terminal alkynes to synthesise 1,2,3-triazoles have been carried out. The modific
- Borah, Bibek Jyoti,Dutta, Dipanka,Saikia, Partha Pratim,Barua, Nabin Chandra,Dutta, Dipak Kumar
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experimental part
p. 3453 - 3460
(2012/01/15)
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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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- N -Heterocyclic donor- and acceptor-type ligands based on 2-(1 H -[1,2,3]Triazol-4-yl)pyridines and their ruthenium(II) complexes
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New 2-(1H-[1,2,3]triazol-4-yl)pyridine bidentate ligands were synthesized as bipyridine analogs, whereas different phenylacetylene moieties of donor and acceptor nature were attached at the 5-position of the pyridine unit. The latter moieties featured a crucial influence on the electronic properties of those ligands. The N-heterocyclic ligands were coordinated to ruthenium(II) metal ions by using a bis(4,4′-dimethyl-2,2′-bipyridine)ruthenium(II) precursor. The donor or acceptor capability of the 2-(1H-[1,2,3]triazol-4-yl) pyridine ligands determined the quantum yield of the resulting ruthenium(II) complexes remarkably. Separately, 2-([1,2,3]triazol-4-yl)pyridine ligands are known to be potential quenchers, but using these new ligand systems led to room temperature emission of the corresponding ruthenium(II) complexes. The compounds have been fully characterized by elemental analysis, high-resolution ESI mass spectrometry, 1H and 13C NMR spectroscopy, and X-ray crystallography. Theoretical calculations for two ruthenium(II) complexes bearing a donor and acceptor unit, respectively, were performed to gain a deeper understanding of the photophysical behavior.
- Happ, Bobby,Escudero, Daniel,Hager, Martin D.,Friebe, Christian,Winter, Andreas,Goerls, Helmar,Altuntas, Esra,Gonzalez, Leticia,Schubert, Ulrich S.
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experimental part
p. 4025 - 4038
(2010/08/06)
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- Synthesis of antitumour (1H-1,2,3-triazol-4-yl)-4-hydroxycyclohexa-2,5- dien-1-ones by copper-catalysed Huisgen cycloadditions
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4-Ethynyl-4-hydroxycyclohexa-2,5-dien-1-one 5 undergoes cycloaddition reactions with a range of substituted azides in the presence of copper salts to form 1,4-disubstituted triazoles 8-11 bearing the 4-hydroxycyclohexa-2,5-dien-1- one (quinol) pharmacopho
- McCarroll, Andrew J.,Matthews, Charles S.,Wells, Geoffrey,Bradshaw, Tracey D.,Stevens, Malcolm F. G.
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body text
p. 2078 - 2084
(2010/07/04)
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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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- 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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experimental part
p. 2063 - 2069
(2011/03/17)
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- Direct functionalization of self-assembled nanotubes overcomes unfavorable self-assembling processes
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Diamides containing alkyne and azido were self-assembled into nanotubes and were reacted under their self-assembled state with small molecules by "click chemistry"; the resulting compounds remain self-assembled into new nanotubes that cannot be formed by
- Nguyen, Thi-Thanh-Tam,Simon, Franois-Xavier,Schmutz, Marc,Mesini, Philippe J.
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supporting information; experimental part
p. 3457 - 3459
(2009/12/26)
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- Formation of giant amphiphiles by post-functionalization of hydrophilic protein-polymer conjugates
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A novel, generic method for the synthesis of families of tri-block protein-polymer giant amphiphiles was designed and developed. We have synthesized a hydrophilic α-maleimido poly-1-alkyne with Mn = 9.5 kDa (1H-NMR) and narrow PDi (1.15 as measured by SEC) via ATRP (Atom Transfer Radical Polymerization). This polymer was succesfully coupled to BSA to afford a hydrophilic multifunctional bioconjugate which was isolated using protein purification techniques and fully characterized. Following the post-functionalization approach, we introduced hydrophobicity to the resulting hydrophilic biohybrid by a straightforward, high yield "click"- chemistry cycloaddition step. The resulting tri-block protein-polymer amphiphiles were isolated and showed interesting aggregation patterns (TEM, confocal microscopy). The Royal Society of Chemistry 2007.
- Le Droumaguet, Benjamin,Mantovani, Giuseppe,Haddleton, David M.,Velonia, Kelly
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p. 1916 - 1922
(2008/02/08)
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- Oxidation of azides by the HOF·CH3CN: A novel synthesis of nitro compounds
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The HOF·CH3CN complex, readily prepared by passing F 2 through aqueous acetonitrile, is an exceptionally efficient oxygen transfer agent. It is unique in its capacity to oxidize various azides into the corresponding nitro derivatives. This method requires short reactions times and room temperature or below, and the desired nitro compounds were usually isolated in very good yields. The respective nitroso derivatives are believed to be the intermediates in this reaction. Functional groups such as aromatic rings, ketones, nitriles, halides, alcohols, and esters are tolerated. Sulfides react with HOF·CH3CN usually at the same rate as azides. Amines and olefins, however, react faster, so they have to be protected first. Nitro derivatives with various oxygen isotopes can be made using the labeled H 18OF·CH3CN. In the case of chiral azides the stereochemistry around the nitrogen-bonded carbons is retained.
- Carmeli, Mira,Rozen, Shlomo
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p. 4585 - 4589
(2007/10/03)
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- Process for the preparation of azide derivatives
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A process for the preparation of azide derivatives useful as drugs, perfumes or intermediates of dyes by reacting an alcohol derivative with di-p-nitrophenyl phosphorazidate in the presence of 1,8-diazabicyclo[5.4.0]-7-undecene.
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- Efficient method for the one-pot azidation of alcohols using bis(p-nitrophenyl) phosphorazidate
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The direct stereoselective conversion of various alcohols and hexopyranoses into the corresponding alkyl azides and glycosyl azides, respectively, is efficiently accomplished by using bis(p-nitrophenyl) phosphorazidate and DBU.
- Mizuno, Masanori,Shioiri, Takayuki
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p. 2165 - 2166
(2007/10/03)
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- Direct Conversion of Activated Alcohols to Azides Using Diphenyl Phosphorazidate. A Practical Alternative to Mitsunobu Conditions
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Fourteen alcohols were converted to their corresponding azides with inversion of configuration using diphenyl phosphorazidate and DBU.
- Thompson, Andrew S.,Humphrey, Guy R.,DeMarco, Anthony M.,Mathre, David J.,Grabowski, Edward J. J.
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p. 5886 - 5888
(2007/10/02)
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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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p. 1245 - 1248
(2007/10/02)
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- A Facile Reduction of Azides to Amines Using Hydrazine
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A variety of alkyl and aryl azides were reduced in high yields to the corresponding amines by reaction with hydrazine in refluxing methanol in the presence of palladium.
- Malik, A. A.,Preston, S. B.,Archibald, T. G.,Cohen, M. P.,Baum, K.
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p. 450 - 451
(2007/10/02)
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- Novel Functional Group Transformations involving Alkyl Phenyl Selenones
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Alkyl phenyl selenones readily undergo substitution reactions, and are valuable precursors of epoxides on reaction with aldehydes inthe presence of bases.
- Krief, Alain,Dumont, Willy,Denis, Jean-Noel
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p. 571 - 572
(2007/10/02)
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