- Hybrid Pyrazolyl-1,2,3-Triazolyl Tripodal Tetraamine Ligands: Click Synthesis and Cobalt(III) Complexes
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A family of tripodal tetraamine ligands incorporating two pyrazolyl and one 1,2,3-triazolyl donor arm have been synthesized in modest-to-excellent yields (42-90%) using the copper(i)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Mono-, bis-, and tris-tripodal ligand scaffolds were readily generated using this method. The coordination chemistry of the ligands with cobalt(iii) ions has been studied, and cobalt(iii) carbonato complexes of the ligands have been isolated and characterized spectroscopically and crystallographically. X-ray crystallography and NMR spectroscopy of the mono-metallic complexes showed that racemic mixtures of the cis-isomer are formed selectively. The di- and tri-metallic systems could not be crystallized, but NMR spectroscopy indicates that these compounds were isolated as mixtures of stereoisomers.
- Cubanski, John R.,Reish, Matthew E.,Blackman, Allan G.,Steel, Peter J.,Gordon, Keith C.,McMorran, David A.,Crowley, James D.
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- A simple copper-catalysed tandem cyclisation of ynamides leading to triazolo-1,2,4-benzothiadiazine-1,1-dioxides in PEG-400 medium
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An efficient one-pot approach for the synthesis of fused triazolo 1,2,4-benzothiadiazine-1,1-dioxide derivatives from functionalised ynamides and sodium azide in the presence of CuI using PEG-400 as the medium is described. The cyclisation process involves intermolecular C-N bond formation and subsequent cycloaddition between ynamide and azide. Thus three new C-N bonds are formed in a single step. It is also demonstrated that the triazole ring in triazolo-1,2,4-benzothiadiazine-1,1-dioxide can be readily decyclised in the presence of glacial acetic acid with the elimination of molecular nitrogen.
- Reddy, Alla Siva,Reddy, M. Nagarjuna,Swamy, K. C. Kumara
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- Pyridyl-Functionalised 3H-1,2,3,4-Triazaphospholes: Synthesis, Coordination Chemistry and Photophysical Properties of Low-Coordinate Phosphorus Compounds
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Novel conjugated, pyridyl-functionalised triazaphospholes with either tBu or SiMe3 substituents at the 5-position of the N3PC heterocycle have been prepared by a [3+2] cycloaddition reaction and compared with structurally related, triazole-based systems. Photoexcitation of the 2-pyridyl-substituted triazaphosphole gives rise to a significant fluorescence emission with a quantum yield of up to 12 %. In contrast, the all-nitrogen triazole analogue shows no emission at all. DFT calculations indicate that the 2-pyridyl substituted systems have a more rigid and planar structure than their 3- and 4-pyridyl isomers. Time-dependent (TD) DFT calculations show that only the 2-pyridyl-substituted triazaphosphole exhibits similar planar geometry, with matching conformational arrangements in the lowest energy excited state and the ground state; this helps to explain the enhanced emission intensity. The chelating P,N-hybrid ligand forms a ReI complex of the type [(N^N)Re(CO)3Br] through the coordination of nitrogen atom N2 to the metal centre rather than through the phosphorus donor. Both structural and spectroscopic data indicate substantial π-accepting character of the triazaphosphole, which is again in contrast to that of the all-nitrogen-containing triazoles. The synthesis and photophysical properties of a new class of phosphorus-containing extended π systems are described. Mix and match: Hitherto unknown pyridyl-functionalized triazaphospholes have been synthesized by a [3+2] cycloaddition reaction starting from phosphaalkynes and pyridyl-substituted azides (see figure). Both experiments and theoretical calculations established these compounds as novel π-conjugated organophosphorus derivatives for future optoelectronic applications.
- Sklorz, Julian A. W.,Hoof, Santina,Rades, Nadine,Derycke, Nicolas,K?ncz?l, Lászl?,Szieberth, Dénes,Weber, Manuela,Wiecko, Jelena,Nyulászi, Lászl?,Hissler, Muriel,Müller, Christian
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- Homogeneous catalyst containing Pd in the reduction of aryl azides to primary amines
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Abstract: Commercially available dichloro[2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]palladium(II) (BINAP.PdCl2) homogeneous catalyst was used for the reduction of aryl azides to primary amines. The reactions were carried out in water and yields above 95% were obtained in a short time. Sodium borohydride was used as the reducing reagent. A number of aryl azide derivatives have been converted into primary amines, thanks to the hydrogen gas released by sodium borohydride with the help of water and catalyst. Graphical Abstract: [Figure not available: see fulltext.] Synopsis Commercially available dichloro[2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]palladium(II) (BINAP.PdCl2) homogeneous catalyst was used for the reduction of aryl azides to primary amines. The reactions were carried out in water and yields above 95% were obtained in a short time. Sodium borohydride was used as the reducing reagent. A number of aryl azide derivatives have been converted into primary amines, thanks to the hydrogen gas released by sodium borohydride with the help of water and catalyst.
- Aydinli, E.,Cantopcu, E.,Goksu, H.
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- Iron-mediated desulphurization approach: synthesis of cyanamides and their conversions
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The iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology. All the reactions are rapid, facile, and accomplished at room temperature. A variety of substrates readily underwent the optimized reaction conditions to provide their respective target products in good to excellent yields. Furthermore, we have confirmed that no other by-products could be identified during our experimental reaction process. Graphical abstract: Iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology.[Figure not available: see fulltext.].
- Nannapaneni, Madhavi,Pendem, Venkata Bhavanarushi,Tamminana, Ramana
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- Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions
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Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.
- Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter
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supporting information
p. 133 - 146
(2021/11/04)
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- Immobilization of vitamin B1 on the magnetic dialdehyde starch as an efficient carbene-type support for the copper complexation and its catalytic activity examination
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Since the starch biopolymer is an available and inexpensive matrix with modifiable functionality and stabilization capability for metal ions, in this report, we oxidized it to dialdehyde form for the further functionalization with vitamin B1 as a green σ-donor and π-acceptor carbene type ligand. Immobilization of vitamin B1 on this biopolymer was done through imine bond formation between NH2 groups of aminopyrimidine segment of vitamin B1 and aldehyde functional groups of starch oxide. Thiazolium heterocycle part in this biomolecule provided a carbene type precursor for the metal complexation. After the magnetization process by using of Fe3O4 nanoparticles that lead to quick and facile magnetic separation and metal catalyst recycling, copper ions immobilized on the magnetic support (5.9 wt% Cu, 0.93 mmol/g). The prepared copper N-heterocyclic carbene complex (Fe3O4@DAS@VB1@CuCl nanocomposite) was characterized by FT-IR, SEM, EDX, XRD, VSM, TGA and ICP-OES analysis and then its catalytic activity investigated in azidonation of arylboronic acids and also one-pot coupling reaction of the synthesized aryl azides with phenylacetylene. 1,4-Diaryl 1,2,3-triazoles were obtained in excellent yields (≥90%) at proper reaction times (30–200 min). The magnetic catalyst was recovered by a magnetic field and reused in azidation reaction up to 7 cycle.
- Abbaspour, M.,Mohammadi Ziarani, G.,Rafiee, F.
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- Design and synthesis of novel diosgenin-triazole hybrids targeting inflammation as potential neuroprotective agents
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Alzheimer's disease is a progressive neurodegenerative disease, and its incidence is expected to increase as the global population ages. Recent studies provide increasing evidence that inflammation plays a key role in the pathogenesis and progression of AD. Diosgenin, an active ingredient in Dioscorea nipponica Makino, is a promising bioactive lead compound in the treatment of Alzheimer's disease, which exhibited anti-inflammatory activity. To search for more efficient anti-Alzheimer agents, a series of novel diosgenin-triazolyl hybrids were designed, synthesized, and their neuroprotective effects against oxygen-glucose deprivation-induced neurotoxicity and LPS-induced NO production were evaluated. Most of these new hybrids displayed better activities than DIO. In particular, the promising compound L6 not only demonstrated an excellent neuroprotective effect but also showed the best anti-inflammatory activity. The structure-activity relationship study illustrated that the introduction of benzyl or phenyl triazole did improve the activity, and the introduction of benzyl triazole was better than that of phenyl triazole. The results we obtained showed that the diosgenin skeleton could be a promising structural template for the development of new anti-Alzheimer drug candidates, and compound L6 has the potential to be an important lead compound for further research.
- Huang, Yi,Huang, Weiwei,Yang, Guixiang,Wang, Rui,Ma, Lei
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supporting information
(2021/05/21)
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- Efficient Pd(ii)-catalyzed regioselectiveortho-halogenation of arylcyanamides
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Regioselectiveortho-halogenation of arylcyanamides using a Pd(ii) catalyst has been established under mild reaction conditions. Either electron-donating or electron-withdrawing groups readily carried out the reaction and produced final products in moderate to good yields. Based on the experimental work, we have confirmed that this method does not undergo a free radical mechanism. Furthermore, we have also attempted this method for practical utility purposes.
- Alam, M. Mujahid,Boddapati, S. N. M.,Bollikolla, Hari Babu,Gugulothu, Sailaja,Tamminana, Ramana,Varala, Ravi
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p. 17176 - 17182
(2021/10/04)
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- Structural and Activity Relationships of 6-Sulfonyl-8-Nitrobenzothiazinones as Antitubercular Agents
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The benzothiazinone (BTZ) scaffold compound PBTZ169 kills Mycobacterium tuberculosis by inhibiting the essential flavoenzyme DprE1, consequently blocking the synthesis of the cell wall component arabinans. While extraordinarily potent against M. tuberculosis with a minimum inhibitory concentration (MIC) less than 0.2 ng/mL, its low aqueous solubility and bioavailability issues need to be addressed. Here, we designed and synthesized a series of 6-methanesulfonyl substituted BTZ analogues; further exploration introduced five-member aromatic heterocycles as linkers to attach an aryl group as the side chain. Our work led to the discovery of a number of BTZ derived compounds with potent antitubercular activity. The optimized compounds 6 and 38 exhibited MIC 47 and 30 nM, respectively. Compared to PBTZ169, both compounds displayed increased aqueous solubility and higher stability in human liver microsomes. This study suggested that an alternative side-chain modification strategy could be implemented to improve the druglike properties of the BTZ-based compounds.
- Chiarelli, Laurent R.,Fan, Dongguang,Han, Quanquan,Lu, Yu,Qiao, Chunhua,Shi, Rui,Stelitano, Giovanni,Wang, Bin,Huszár, Stanislav,Miku?ová, Katarína,Savková, Karin
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supporting information
p. 14526 - 14539
(2021/10/26)
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- Design, Synthesis and Evaluation of a Series of 1,5-Diaryl-1,2,3-triazole-4-carbohydrazones as Inhibitors of the YAP-TAZ/TEAD Complex
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Starting from our previously reported hit, a series of 1,5-diaryl-1,2,3-triazole-4-carbohydrazones were synthesized and evaluated as inhibitors of the YAP/TAZ-TEAD complex. Their binding to hTEAD2 was confirmed by nanodifferential scanning fluorimetry, an
- Gibault, Floriane,Sturbaut, Manon,Coevoet, Mathilde,Pugnière, Martine,Burtscher, Ashley,Allemand, Frédéric,Melnyk, Patricia,Hong, Wanjin,Rubin, Brian P.,Pobbati, Ajaybabu V.,Guichou, Jean-Fran?ois,Cotelle, Philippe,Bailly, Fabrice
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p. 2823 - 2844
(2021/07/10)
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- Concise synthesis of: N -phosphorylated amides through three-component reactions
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N-Phosphorylated amides continue to be an unparalleled asset for the development of pharmaceutical molecules, and the importance of this framework has inspired researchers to look for concise and efficient methods for the synthesis of this unit. In this work, a new strategy was developed in which a one-pot synthesis of N-phosphorylated amides was achieved by a three-component reaction with carboxylic acids, phosphorus chlorides and azides under mild reaction conditions. To our knowledge, this is the first study in which this framework was constructed through a multicomponent reaction, which is innovative, efficient and economical. This journal is
- Yang, Shang-Dong,Zhang, Tao,Zhou, Linlin,Zhu, Yuan-Yuan
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supporting information
p. 9417 - 9421
(2021/12/09)
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- Discovery of new tranylcypromine derivatives as highly potent LSD1 inhibitors
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Tranylcypromine (TCP)-based structural modifications lead to the discovery of new LSD1 inhibitors, of which compounds 26b and 29b effectively inhibit LSD1 with the IC50 values of 17 and 11 nM, respectively and also show good selectivity over MAO-B. Mechanistic studies showed that compound 29b concentration-dependently induced H3K4me1/2 accumulation in LSD1 overexpressed MGC-803 cells and also inhibited metastasis of MGC-803 cells. Collectively, both compounds could be promising lead compounds for further investigation.
- Huang, Ming-Jie,Guo, Jia-Wen,Fu, Yun-Dong,You, Ya-Zhen,Xu, Wen-Yu,Song, Ting-Yu,Li, Ran,Chen, Zi-Tong,Huang, Li-Hua,Liu, Hong-Min
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supporting information
(2021/04/12)
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- Synthetic access to ring-expanded N-heterocyclic carbene (Re-NHC) copper complexes and their performance in click chemistry
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The facile syntheses of ring-expanded N-heterocyclic carbene (RE-NHC) copper(I) halide complexes are reported. The method makes use of a weak inorganic base in a green solvent. The reaction times can be greatly reduced by use of this weak-base route under microwave irradiation. The easy access to these complexes permits an evaluation of the catalytic activity and reaction profiling of [Cu(RE-NHC)X] complexes in the Huisgen 1,3-cycloaddition reaction.
- Bouchet, Damien,Cazin, Catherine S. J.,Hall, Jonathan W.,Mahon, Mary F.,Whittlesey, Michael K.
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p. 1252 - 1261
(2021/05/29)
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- Design, synthesis and biological evaluation of second-generation benzoylpiperidine derivatives as reversible monoacylglycerol lipase (MAGL) inhibitors
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An interesting enzyme of the endocannabinoid system is monoacylglycerol lipase (MAGL). This enzyme, which metabolizes the endocannabinoid 2-arachidonoylglycerol (2-AG), has attracted great interest due to its involvement in several physiological and pathological processes, such as cancer progression. Experimental evidences highlighted some drawbacks associated with the use of irreversible MAGL inhibitors in vivo, therefore the research field concerning reversible inhibitors is rapidly growing. In the present manuscript, the class of benzoylpiperidine-based MAGL inhibitors was further expanded and optimized. Enzymatic assays identified some compounds in the low nanomolar range and steered molecular dynamics simulations predicted the dissociation itinerary of one of the best compounds from the enzyme, confirming the observed structure-activity relationship. Biological evaluation, including assays in intact U937 cells and competitive activity-based protein profiling experiments in mouse brain membranes, confirmed the selectivity of the selected compounds for MAGL versus other components of the endocannabinoid system. An antiproliferative ability in a panel of cancer cell lines highlighted their potential as potential anticancer agents. Future studies on the potential use of these compounds in the clinical setting are also supported by the inhibition of cell growth observed both in cancer organoids derived from high grade serous ovarian cancer patients and in pancreatic ductal adenocarcinoma primary cells, which showed genetic and histological features very similar to the primary tumors.
- Granchi, Carlotta,Bononi, Giulia,Ferrisi, Rebecca,Gori, Eleonora,Mantini, Giulia,Glasmacher, Sandra,Poli, Giulio,Palazzolo, Stefano,Caligiuri, Isabella,Rizzolio, Flavio,Canzonieri, Vincenzo,Perin, Tiziana,Gertsch, Jürg,Sodi, Andrea,Giovannetti, Elisa,Macchia, Marco,Minutolo, Filippo,Tuccinardi, Tiziano,Chicca, Andrea
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- Iodine-Catalyzed Aerobic Diazenylation-Amination of Indole Derivatives
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A mild strategy for consecutive diazenylation and amination of indole moieties has been demonstrated. The functionalization occurs at C3 and C2 carbon atoms, respectively, at the indole scaffold in the presence of catalytic iodine and air at 40 °C in the 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) solvent. It is noteworthy that the aromatic amines are generated in situ by the reaction of aryl hydrazine with iodine. In general, bright red products are obtained in moderate to good yield. Control reactions are conducted to establish the reaction mechanism.
- Sar, Saibal,Tripathi, Ankita,Dubey, Kshatresh Dutta,Sen, Subhabrata
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supporting information
p. 3748 - 3756
(2020/03/04)
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- Efficient and simple synthesis of novel 1,2,3-triazolyl-linked benzimidazolone, molecular docking and evaluation of their antimicrobial activity
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In this study, a novel series of 1,2,3-triazolyl-benzimidazolone derivatives have been synthesized by click reaction of azides with benzimidazolones 2a–b. The latter compounds were prepared with excellent yields (85–97%), the structures of products were determined by spectral analysis. Then, the X-rays crystallographic analysis of compound 7a revealed the self-assembling properties. The new heterocycles were evaluated for their in?vitro antimicrobial activities against Gram-positive and Gram-negative bacteria and against fungi strains. The most tested synthesized compounds showed potent antibacterial and antifungal activities against all tested strains. The compound 6c was found to be the most active, particularly, against Aspergillus niger and Penicillium sp. with the same MIC and MBC of 0.0625 mg/mL. Furthermore, in silico molecular docking studies stipulated a sign of a good correlation between experimental activity and calculated binding affinity. According to the docking results, compound 6d showed minimum binding energy and can be considered as a good antimicrobial agent.
- Adardour, Mohamed,Boutafda, Aziz,Hdoufane, Ismail,Aghraz, Abdellah,Hafidi, Mohamed,Zaballos-García, Elena,Cherqaoui, Driss,Baouid, Abdesselam
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p. 3490 - 3506
(2020/08/19)
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- Chan-Lam-type Azidation and One-Pot CuAAC under CuI-Zeolite Catalysis
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The copper(I)-exchanged zeolite CuI-USY proved to efficiently catalyze the direct azidation of arylboronic acids with sodium azide under simple and practical conditions, namely at room temperature under air with methanol as solvent and without any additive. This easy-to-prepare and cheap catalytic material has been demonstrated to be recyclable and the mild azidation conditions further showed good functional-group tolerance, leading to a variety of substituted (hetero)aryl azides (18 examples). Interestingly, the azidation reaction has been successfully coupled to a CuAAC reaction, thus allowing access to triazoles from arylboronic acids via a one-pot CuI-catalyzed process.
- Clerc, Arnaud,Bénéteau, Valérie,Pale, Patrick,Chassaing, Stefan
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p. 2060 - 2065
(2020/03/03)
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- Preparation of aryl azides of aryl boronic acids and one-pot synthesis of 1,4-diaryl-1,2,3-triazoles by a magnetic cysteine functionalized GO–CuI/II nanocomposite
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A mixed CuI/CuIIcatalyst based on magnetic cysteine functionalized graphene oxide (CuI/II@Cys-MGO) was prepared and used for the azidonation reaction of aryl boronic acids and one-pot synthesis of 1,4-diaryl ?1,2,3-triazoles. Aryl azides were obtained in good yields and short reaction times via cross-coupling of aryl boronic acids with sodium azide in the presence of CuII catalytic species in this catalytic system. The azide-alkyne cycloaddition reaction was catalyzed by CuI catalytic species in CuI/II@Cys-MGO nanocomposite.
- Rafiee, Fatemeh,Khavari, Parvaneh
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- New α-Hydroxy-1,2,3-triazoles and 9H-Fluorenes-1,2,3-triazoles: H Synthesis and Evaluation as Glycine Transporter 1 Inhibitors
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Two series of new compounds containing 1,2,3-triazole moiety were designed as putative GlyT1 inhibitors aiming the discovery of new hits with activity in cognitive disorders. 1,4-Disubstituted α-hydroxy-1,2,3-triazoles were obtained as racemates in moderate to good yields by the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction (click chemistry) as the key step between propargyl alcohols and aryl azides, previously prepared from anilines or boronic acids. Benzo[c]chromene-triazoles were planned to be obtained by palladium-catalyzed C?H activation using [bis(trifluoroacetoxy)iodobenzene] (PhI(TFA)2) of some α-hydroxy-1,2,3-triazoles, since benzo[c]chromenes are also privileged groups with several biological activities, including to the central nervous system. Unexpectedly, 9H-fluorenes-1,2,3-triazoles, instead of benzo[c]chromenetriazoles, were obtained by Friedel-Crafts alkylation reaction. The two series of compounds were tested for inhibition of the glycine transporter (rat GlyT1 isoform) but only the α-hydroxy-1,2,3-triazole 9b was active (half maximal inhibitory concentration (IC50) = 8.0 μM).
- Buarque, Camilla D.,Guimar?es, Marilia Z.,López?Corcuera, Beatriz,Neto, Jo?o Gon?alves,No?l, Fran?ois,Silva, Rafaela R.,da Silva, Veronica D.
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p. 1258 - 1269
(2020/10/14)
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- Water Oxidation at Neutral pH using a Highly Active Copper-Based Electrocatalyst
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The sluggish kinetics of the oxygen evolution reaction (OER) at the anode severely limit hydrogen production at the cathode in water splitting systems. Although electrocatalytic systems based on cheap and earth-abundant copper catalysts have shown promise
- Younus, Hussein A.,Zhang, Yan,Vandichel, Matthias,Ahmad, Nazir,Laasonen, Kari,Verpoort, Francis,Zhang, Ce,Zhang, Shiguo
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p. 5088 - 5099
(2020/08/12)
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- Regioselective synthesis of 4-fluoro-1,5-disubstituted-1,2,3-triazoles from synthetic surrogates of α-fluoroalkynes
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α-Fluoroalkynes are elusive molecules due to their instability and inaccessibility. Here, we show that α-fluoronitroalkenes can serve as synthetic surrogates of α-fluoroalkynes in [3+2] cycloaddition reactions with organic azides facilitated by a catalytic amount of trifluoroacetic acid (TFA). This work provides the first regioselective method to access 4-fluoro-1,5-disubstituted-1,2,3-triazoles.
- Jana, Sampad,Adhikari, Sweta,Cox, Michael R.,Roy, Sudeshna
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supporting information
p. 1871 - 1874
(2020/02/20)
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- 2-indolone-triazole anti-tumor compound as well as preparation method and application thereof
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The invention belongs to the technical field of medicines, and relates to a compound with antitumor activity and a specific chemical structure, in particular to a 2-indolone antitumor compound with a1,2,3-triazole structure as well as a preparation method and application thereof. The structural general formula of the 2-indolone-triazole anti-tumor compound is specifically shown in the specification. Pharmacological research shows that the compound has a strong inhibition effect on human VEGFR-2 enzyme and has a certain inhibition capability on the proliferation of human lung cancer H460 cells. The preparation method of the 2-indolone with the 1, 2, 3-triazole structure is simple and feasible, relatively high in yield and easy for large-scale production.
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Paragraph 0053-0055
(2020/06/05)
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- Photolysis and Pyrolysis of Phenyltetrazoles: Formation of Phenylcarbodiimide, N-Phenylnitrile Imine, Phenylnitrene, Indazole, and Fulvenallene
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Photolysis of 1-phenyltetrazole 2b at either 193 or 266 nm in a Ne matrix as well as flash vacuum pyrolysis (FVP) of the same compound with isolation of the products in Ne matrix generate phenylcarbodiimide PhN=C=NH 6 very efficiently as the principal product in an almost pure state. Minor amounts of phenyl azide 8 and 1-azacyclohepta-1,2,4,6-tetraene 10, the product of ring expansion of phenylnitrene, are also formed, and the amounts of both substances increase as a function of photolysis time. The photolysis of 2-phenyltetrazole 1b in a Ne matrix at 266 nm for 0.5 min generates the allenic N-phenylnitrile imine PhN=N(+)=CH(–) 3b, absorbing strongly and cleanly at 2021 cm–1 in the IR spectrum. At longer photolysis times peaks ascribed to phenyl azide, phenylnitrene, 1-azacycloheptatetraene, and phenylcarbodiimide 6 become prominent. FVP of 2-phenyltetrazole yields indazole 15 as the major product together with a small amount of phenylcarbodiimide 6. Indazole formation is ascribed to cyclization of the nitrile imine in the ground state. It is not formed on FVP of 1-phenyltetrazole in agreement with the computational result that the thermodynamically most favourable path for rearrangement of the putative N-phenylimidoylnitrene 5b yields phenylcarbodiimide 6 rather than phenylnitrile imine 3b. Further pyrolysis of indazole affords a minor yield of fulvenallene 18.
- Zhao, Xiaofang,Liu, Qian,Feng, Ruijuan,Zeng, Xiaoqing,Wentrup, Curt
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p. 6945 - 6950
(2019/11/20)
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- Borane Adducts of Hydrazoic Acid and Organic Azides: Intermediates for the Formation of Aminoboranes
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The reaction of HN3 with the strong Lewis acid B(C6F5)3 led to the formation of a very labile HN3?B(C6F5)3 adduct, which decomposed to an aminoborane, H(C6F5)NB(C6F5)2, above ?20 °C with release of molecular nitrogen and simultaneous migration of a C6F5 group from boron to the nitrogen atom. The intermediary formation of azide–borane adducts with B(C6F5)3 was also demonstrated for a series of organic azides, RN3 (R=Me3Si, Ph, 3,5-(CF3)2C6H3), which also underwent Staudinger-like decomposition along with C6F5 group migration. In accord with experiment, computations revealed rather small barriers towards nitrogen release for these highly labile azide adducts for all organic substituents except R=Me3Si (m.p. 120 °C, Tdec=189 °C). Hydrolysis of the aminoboranes provided C6F5-substituted amines, HN(R)(C6F5), in good yields.
- Bl?sing, Kevin,Bresien, Jonas,Labbow, René,Michalik, Dirk,Schulz, Axel,Thomas, Max,Villinger, Alexander
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supporting information
p. 6540 - 6544
(2019/04/10)
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- Synthesis and Evaluations of “1,4-Triazolyl Combretacoumarins” and Desmethoxy Analogs
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1,4-Triazolyl combretacoumarins have been prepared by linking the trimethoxyarene unit of combretastatin A4 with coumarins, via a 1,2,3-triazole. For this, 4-azidocoumarins were accessed by a sequential two-step, one-pot reaction of 4-hydroxycoumarins with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), followed by reaction with NaN3. In the reaction with BOP, a coumarin-derived phosphonium ion intermediate seems to form, leading to an O4-(benzotriazolyl)coumarin derivative. For the CuAAC reaction of azidocoumarins with 5-ethynyl-1,2,3-trimethoxybenzene, catalytic [(MeCN)4Cu]PF6 in CH2Cl2/MeOH with 2,6-lutidine, at 50 oC, was suitable. The 4-azidocoumarins were less reactive as compared to PhN3 and the NBO coefficients of the azido groups were compared by DFT analysis. Compound solubility was a problem in biological assays. On the basis of the biological and solubility data of one 1,4-triazolyl combretacoumarin, four analogs lacking one or two methoxy groups were synthesized. Reactivity differences among the phenylacetylenes were noted and the NBO coefficients of the alkynes were compared by DFT analysis. In cytotoxicity assays, 1-phenyl-4-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole showed activity in CEM and MDA-MB-231 cell lines by apoptosis. The desmethoxy 6-bromo-4-(4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one also showed cytotoxicity against the two cell lines, but this did not appear to be consistent with apoptosis. The antiviral activity of the compounds was unremarkable.
- Khandaker, Tashrique A.,Hess, Jessica D.,Aguilera, Renato,Andrei, Graciela,Snoeck, Robert,Schols, Dominique,Pradhan, Padmanava,Lakshman, Mahesh K.
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p. 5610 - 5623
(2019/08/16)
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- Method for preparing 1,2,3-triazole compound by heterogeneous copper catalysis in one pot
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The invention relates to a method for preparing a 1-aryl-4-substituted-1,2,3-triazole compound shown as a formula (II). The method comprises the following steps: mixing arylboronic acid (1), NaN3, a heterogeneous copper catalyst and solvent water, performing a stirring reaction at 25-60 DEG C for 4-8 hours, performing TLC (thin-layer chromatography) monitoring till the arylboronic acid (1) is completely converted, replacing air in the reaction system by using N2, adding a terminal alkyne (2), performing a reaction at 40-80 DEG C for 6-10 hours under the protection of N2, and performing post-treatment on the reaction solution to obtain a product (II). By adopting the preparation method, Cu-coated SBA-15-PTAA is used as a catalyst, a series of 1-aryl-4-substituted-1,2,3-triazole compounds are prepared through a one-pot Chan-Lam/Click series method without additionally adding a reducing agent, the developed catalytic method is green, safe and economical, the amount of three wastes (wastegas, waste water and industrial residue) is small, the yield of a target product is high, and the substrate application range is wide.
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Paragraph 0050-0051
(2019/12/25)
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- A Simple Efficient Click Synthesis of Novel Crown Ethers Containing 1,2,3-Triazole Moieties
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Novel crown ether derivative containing 1,4-disubstituted-1,2,3-triazole moieties were synthesized. At the first step of the synthesis 4,13-diaza-18-crown-6 and 4-aminobenzo-15-crown-5 were converted into terminal alkynes, which were then subjected to copper(I)-catalyzed alkyne-azide coupling (CuAAC) in methylene chloride. This coupling reaction was performed according to the concept of click chemistry, using an Amberlyst A-21-supported copper(I) iodide catalyst.
- Elamari,Ouerghui,Ammari,Girard
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p. 1785 - 1790
(2020/01/11)
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- A reusable polymer-supported copper(I) catalyst for triazole click reaction on water: An experimental and computational study
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In the search for establishing a clickable copper-catalysed (3?+?2) Huisgen azide–alkyne cycloaddition (CuAAC) reaction under strict conditions, in particular in terms of preventing the presence of copper particles/traces in reaction products and using an environmentally benign medium such as water, we describe here the synthesis of an aminomethyl polystyrene-supported copper(I) catalyst (Cu(I)-AMPS) and its characterization by means of Fourier transform infrared and energy-dispersive X-ray spectroscopies and scanning electron microscopy. Cu(I)-AMPS was found to be highly active in the CuAAC reaction of various organic azides with alkynes affording the corresponding 1,4-disubstituted 1,2,3-triazoles in a regioselective manner in air at room temperature and using water as solvent. The insolubility and/or partial solubility of the organic azide and alkyne precursors as well as the heterogeneous Cu(I)-AMPS catalytic system points to the occurrence of the cycloaddition at the organic–water interface ‘on water’ affording quantitative yields of water-insoluble 1,2,3-triazoles. A mechanistic study was performed using density functional theory aiming at explaining the observed reactivity and selectivity of the Cu (I)-AMPS catalyst in CuAAC reactions.
- Bahsis, Lahoucine,Ben El Ayouchia, Hicham,Anane, Hafid,Pascual-álvarez, Alejandro,De Munno, Giovanni,Julve, Miguel,Stiriba, Salah-Eddine
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- Reactions of α-haloacroleins with azides: Highly regioselective synthesis of formyl triazoles
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A general metal-free route to 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles was developed. α-Haloacroleins reacted with organic azides in a DMSO/H2O mixture solvent at room temperature to produce 1,4-disubstituted triazoles (up to 99%) with exclusive regioselectivities. This protocol is convenient and scalable with a broad substrate scope including aliphatic and aromatic azides. The resulting triazoles exhibited an aldehyde group at the C4 position and demonstrated synthetic utilizations. One 1,2,3-triazole compound containing diastereotopic protons was also identified.
- Zhang, Dongsheng,Fan, Yingzhu,Yan, Zhongliang,Nie, Yi,Xiong, Xingquan,Gao, Lizhu
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supporting information
p. 4211 - 4216
(2019/08/07)
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- Design, synthesis and biological evaluation of new steroidal β-triazoly enones as potent antiproliferative agents
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β-Triazoly enones are biologically interesting scaffolds, incorporation of such scaffolds into the steroid nucleus may generate new bioactive steroids and further enrich structural types of steroids. In this work, a series of new steroidal β-triazoly enon
- Zhao, Jian-Wei,Guo, Jia-Wen,Huang, Ming-Jie,You, Ya-Zhen,Wu, Zeng-Hui,Liu, Hong-Min,Huang, Li-Hua
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supporting information
(2019/07/12)
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- Design, synthesis and antibacterial evaluation of novel 15-membered 11a-azahomoclarithromycin derivatives with the 1, 2, 3-triazole side chain
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Macrolides are widely prescribed in clinic to treat various respiratory tract infections. However, due to their inappropriate use, the prevalence of macrolide-resistant strains among clinical isolates has become a concern for public health. Therefore, nov
- Qin, Yinhui,Teng, Yuetai,Ma, Ruixin,Bi, Fangchao,Liu, Zhiyang,Zhang, Panpan,Ma, Shutao
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p. 321 - 339
(2019/07/18)
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- Leucine ureido derivatives as aminopeptidase N inhibitors using click chemistry. Part II
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Aminopeptidase N (APN) has been proved to be deeply associated with cancer angiogenesis, metastasis and invasion. Therefore, APN gains increasing attention as a promising anti-tumor target. In the current study, we report the design, synthesis, biological evaluation and structure-activity relationship of one new series of leucine ureido derivatives containing the 1,2,3-triazole moiety. Among them, compound 31f was identified as the best APN inhibitor with IC50 value being two orders of magnitude lower than that of the positive control bestatin. Compound 31f possessed selective cytotoxicity to several tumor cell lines over the normal cell line human umbilical vein endothelial cells (HUVECs). Notably, when combined with 5-fluorouracil (5-Fu), 31f exhibited synergistic anti-proliferation effect against several tumor cell lines. At the same concentration, 31f exhibited much better anti-angiogenesis activities than bestatin in the HUVECs capillary tube formation assay and the rat thoracic aorta rings test. In the in vitro anti-invasion assay, 31f also exhibited superior potency over bestatin. Moreover, considerable in vivo antitumor potencies of 31f alone or in combination with 5-Fu were observed without significant toxic signs in a mouse heptoma H22 tumor transplant model.
- Cao, Jiangying,Zang, Jie,Kong, Xiujie,Zhao, Chunlong,Chen, Ting,Ran, Yingying,Dong, Hang,Xu, Wenfang,Zhang, Yingjie
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p. 978 - 990
(2019/02/09)
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- Facile immobilization of copper(I) acetate on silica: A recyclable and reusable heterogeneous catalyst for azide–alkyne clickable cycloaddition reactions
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The structurally well-defined copper(I) acetate was immobilized on silica gel via electrostatic interactions. The catalytic activity of the immobilized catalyst Cu(I)–SiO2 was examined in the click synthesis of 1,2,3-triazoles in water/ethanol
- Aflak,El Ayouchia, Hicham Ben,Bahsis, Lahoucine,Anane,Laamari, Rachid,Pascual-Alvarez, Alejandro,Armentano, Donatella,Stiriba, Salah-Eddine
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p. 630 - 638
(2019/07/10)
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- 16-(1'-aryl-1',2',3'-triazole)methylene-androst-17-ketone derivative
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The invention belongs to the technical field of drug chemistry, and relates to a 16-(1'-aryl-1',2',3'-triazole)methylene-androst-17-ketone derivative as well as a preparation method and application thereof. The compound has the following general formula:
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Paragraph 0024; 0026; 0027
(2019/02/04)
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- Design, synthesis and biological evaluation of novel uracil derivatives bearing 1, 2, 3-triazole moiety as thymidylate synthase (TS) inhibitors and as potential antitumor drugs
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Research on thymidylate synthase inhibitors has been a hot spot for anticancer drug development. Here, based on the structures and pharmacological properties of two types of TS inhibitors, through a molecular assembly principle of drugs design, we designed and synthesized a series of 30 novel uracil derivatives as TS inhibitors. The antiproliferative ability of these compounds was evaluated against four cancer cell lines (A549, OVCAR-3, SGC-7901, and HepG2) by the MTT assay. Most of them showed excellent activities against all the tested cell lines. Furthermore, hTS assay results showed that these compounds have the unique ability to inhibit hTS activity in vitro. Notably, compound 13j exhibited the most potent activity against A549 cells (IC50 = 1.18 μM) and extremely prominent enzyme inhibition (IC50 = 0.13 μM), which was superior to the pemetrexed (PTX, IC50 = 3.29 μM and IC50 = 2.04 μM). Flow cytometric analysis showed the compound 13j could inhibit A549 cells proliferation by arresting the cell cycle in the G1/S phase, then induced the cell apoptosis. Further western blot analysis showed that compound 13j could down-regulate the cycle checkpoint proteins cyclin D1 and cyclin E to inhibit the cell cycle progression, and then induce intrinsic apoptosis by activating caspase-3, and reducing the ratio of bcl-2/bax. All of these results demonstrated that this new structure has potential drug-making properties and provides new ideas for drug development.
- Lu, Guo-qing,Li, Xin-yang,Mohamed O, Kamara,Wang, Depu,Meng, Fan-hao
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p. 282 - 296
(2019/03/27)
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- Design, synthesis and anti-platelet aggregation activity study of ginkgolide-1,2,3-triazole derivatives
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Ginkgolides are the major active component of Ginkgo biloba for inhibition of platelet activating factor receptor. An azide-alkyne Huisgen cycloaddition reaction was used to introduce a triazole nucleus into the target ginkgolide molecules. A series of ginkgolide-1,2,3-triazole conjugates with varied functional groups including benzyl, phenyl and heterocycle moieties was thus synthesized. Many of the designed derivatives showed potent antiplatelet aggregation activities with IC50 values of 5~21 nM.
- Cui, Jian,Hu, Lean,Shi, Wei,Cui, Guozhen,Zhang, Xumu,Zhang, Qing-Wen
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- Imidazo[4,5-c]pyridine derivative and application thereof
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The invention relates to a novel imidazo[4,5-c]pyridine derivative represented by a general formula I, and pharmaceutically acceptable salts, solvates or prodrugs of the novel imidazo[4,5-c]pyridine derivative, wherein the substituent R and R' are defined as in the specification. The invention also relates to an effect of the compound represented by the general formula I in inhibiting an NS5B RNA-dependent RNA polymerase (NS5B polymerase for short) which is necessary in a replication process of hepatitis c virus, also relates to an application of the compound, and pharmaceutically acceptable salts, hydrates or prodrugs of the compound in preparation of medicines for treating viral diseases, and especially relates to an application in preparation of medicines for treating and/or preventinghepatitis c.
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Paragraph 0091; 0092; 0106; 0107
(2019/10/01)
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- Synthesis of (1,2,3‐triazol‐4‐yl)methyl phosphinates and (1,2,3‐Triazol‐4‐yl)methyl phosphates by copper‐catalyzed azide‐alkyne cycloaddition
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An efficient and practical method was developed for the synthesis of new (1,2,3‐triazol‐4‐yl)methyl phosphinates and (1,2,3‐triazol‐4‐yl)methyl phosphates by the copper(I)‐catalyzed azide‐alkyne cycloaddition (CuAAC) of organic azides and prop‐2‐ynyl phos
- Tripolszky, Anna,Németh, Krisztina,Szabó, Pál Tamás,Bálint, Erika
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- Dibenzo[b,e]aza-6,11-diketotriazole compound as well as preparation method and application thereof
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The invention provides a dibenzo[b,e]aza-6,11-diketotriazole compound and a preparation method thereof, belongs to the technical field of medicines, and specifically relates to a 5-((1-(R-phenyl)-1H-1,2,3-triazol-4-yl)methyl)-5H-dibenzo[b,e]aze-6,11-diketone anti-tumor compound as well as a preparation method and application thereof. The compound prepared by the invention has a function of inhibiting tumor activity and has excellent application prospect in the field of design, research and development of anti-tumor drugs; in addition, the preparation method is simple and easy to industrialize.
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Paragraph 0060; 0069; 0070
(2019/09/05)
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- Trimethylsilyl-Induced N-O Bond Cleavage in Nitrous Oxide-Derived Aminodiazotates
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The chemical activation of nitrous oxide (N2O) typically results in O-atom transfer and the extrusion of N2 gas. In contrast, reactions of N-trimethylsilyl (TMS)-substituted amides with N2O give inorganic or organic azides
- Liu, Yizhu,Eymann, Léonard Y. M.,Solari, Euro,Fadaei Tirani, Farzaneh,Scopelliti, Rosario,Severin, Kay
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supporting information
p. 11859 - 11863
(2018/09/25)
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- A green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: Exceptional performance of a Cu2O-CuO-Cu-C nanocomposite
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A convenient, inexpensive and effective route for the preparation of a Cu2O-CuO-Cu-C nanocomposite is described here by applying Cu(ii) as a source of copper. Characterization of the nanocomposite was performed with X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), high-resolution TEM (HR-TEM), field emission scanning electron microscopy (FE-SEM), X-ray photoelectron spectroscopy (XPS), and energy-dispersive X-ray spectroscopy (EDX). Analysis of the data showed that the particles of the nanocomposite are uniformly distributed and show high catalytic activity in the cross-coupling of sodium azide with various aryl iodides and bromides. This nanocomposite has a high level of performance, and even led to the synthesis of the products at room temperature. In addition, this is the first report of the synthesis of aryl azides under both base- and ligand-free conditions. For the first time, both ligand- and base-free conditions were applied for the synthesis of aryl azides, which implies exceptional performance of the Cu2O-CuO-Cu-C nanocomposite. Simultaneous removal of the base and ligand in a green solvent is the main advantage of this reaction. Unfortunately, aryl bromides and aryl iodides with electron-withdrawing functional groups in their scaffold did not give the desired aryl azides.
- Karimzadeh, Morteza,Niknam, Khodabakhsh,Manouchehri, Neda,Tarokh, Dariush
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p. 25785 - 25793
(2018/07/31)
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- DBU-promoted Cu(OAc)2·H2O-catalysed coupling reactions of aryl iodides and sodium azide
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An efficient and simple protocol for the synthesis of aryl azides by the coupling of aryl iodides with sodium azide, in good to excellent yields in DMSO at 95°C under catalysis by Cu(OAc)2·H2O and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), has been established. The optimised loadings of Cu(OAc)2·H2O and DBU were 10 mol% and 15 mol% respectively.
- Jiang, Yuqin,Suo, Huajun,Zhao, Yaru,Li, Xiyong,Sun, Yamin,Li, Xingfeng,Dong, Wenpei,Li, Wei,Zhang, Weiwei,Xu, Guiqing
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p. 247 - 250
(2018/06/29)
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- Synthesis and antimicrobial activity of 4-substituted 1,2,3-triazole-coumarin derivatives
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A new series of coumarin-1,2,3-triazole conjugates with varied alkyl, phenyl and heterocycle moieties at C-4 of the triazole nucleus were synthesized using a copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition reaction of corresponding O-propargylated coumarin (3) or N-propargylated coumarin (6) with alkyl or aryl azides. Based on their minimal inhibitory concentrations (MICs) against selected microorganisms, six out of twenty-six compounds showed significant antibacterial activity towards Enterococcus faecalis (MIC = 12.5–50 μg/mL). Moreover, the synthesized triazoles show relatively low toxicity against human erythrocytes.
- López-Rojas, Priscila,Janeczko, Monika,Kubiński, Konrad,Amesty, ángel,Mas?yk, Maciej,Estévez-Braun, Ana
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- Supported benzimidazole-salen Cu(II) complex: An efficient, versatile and highly reusable nanocatalyst for one-pot synthesis of hybrid molecules
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A novel and efficient nanocatalyst consisting of benzimidazole-salen Cu(II) complex on surface-modified silica (BS-Cu(II)@SiO2) was prepared. The heterogeneous nanocatalyst was characterized by FESEM, TEM, EDX, FT-IR, XRD, ICP, and TGA. The nanocatalyst was used for the one-pot synthesis of some target hybrid molecules. An efficient four component C–H bond activation/[3?+?2] cycloaddition and condensation/cyclization/aromatization sequence toward triazole-benzimidazole derivatives is disclosed. This methodology provides a general and rapid synthetic route to some new triazole-benzimidazole hybrids under mild reaction conditions. In addition, the heterogeneous nanocatalyst can be easily separated from the reaction mixture and used several times without noticeable leaching or loss of its catalytic activity. We believe this interesting one-pot reaction as well as benzimidazole-salen Cu(II) complex pave the way to the design and synthesis of other new hybrid molecules and metal catalysts, respectively.
- Sharghi, Hashem,Aberi, Mahdi,Shiri, Pezhman
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- Rhodium(I)-Catalyzed Azide-Alkyne Cycloaddition (RhAAC) of Internal Alkynylphosphonates with High Regioselectivities under Mild Conditions
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A regioselective method to access fully substituted 1,2,3-triazolyl-4-phosphonates from the internal alkynylphosphonates by rhodium(I)-catalyzed azide-alkyne cycloaddition (RhAAC) under mild conditions is reported. This approach is water and air compatible and has a broad substrate scope, good functional group tolerance, high yields and excellent regioselectivities. Fully substituted 1,2,3-triazolyl-4-phosphonates are directly prepared from the internal alkynylphosphonates by RhAAC with high 1,4-regioselectivities. The gram-scale preparation, application to carbohydrate synthesis and the solid-phase synthesis of triazolyl-4-phosphonates are highlights of this method. (Figure presented.).
- Song, Wangze,Zheng, Nan,Li, Ming,Ullah, Karim,Zheng, Yubin
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supporting information
p. 2429 - 2434
(2018/05/30)
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- Synthesis and In Vitro Evaluation of 1,2,3-triazole-4-chloromethylcoumarins with Antioxidant Activity
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Background: Coumarins are secondary plant metabolites typically found in the species of Asteraceae, Rutaceae and Umbeliferae families which demonstrate several pharmacological properties, including antioxidant activity. As antioxidants, coumarins are know
- Alves, Anna Carolina Schneider,Munhoz, Thaís,Soares, Fabiana Gomes Nascimento,Rockenbach, Liliana,Gauer, Bruna,Kawano, Daniel Fábio,von Poser, Gilsane Lino,Garcia, Solange Cristina,Eifler-Lima, Vera Lucia
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p. 700 - 705
(2018/06/27)
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- Waste-minimised copper-catalysed azide-alkyne cycloaddition in Polarclean as a reusable and safe reaction medium
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Herein we report the first example of a generally useful organic reaction, namely the copper-catalysed azide-alkyne cycloaddition, performed in a Polarclean/water mixture as a reaction medium. The process is very efficient, affording in 24 out of the 26 tested cases the desired triazole in quantitative yields. Product isolation is also very convenient, since the triazoles either precipitate or form a separate liquid phase, without the need to perform chromatographic separations. Moreover, since the metal catalyst is retained in the Polarclean/water phase, the catalyst/reaction medium can be easily reused for consecutive reaction runs, without an apparent loss in efficiency. This methodology is associated with very limited waste production, as evidenced by calculated E-factors in the range 2.6-3.7.
- Luciani, Lorenzo,Goff, Emily,Lanari, Daniela,Santoro, Stefano,Vaccaro, Luigi
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supporting information
p. 183 - 187
(2018/01/17)
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- Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling
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Twelve 1,5-disubtituted and fourteen 5-substituted 1,2,3-triazole derivatives bearing diaryl or dialkyl phosphines at the 5-position were synthesized and used as ligands for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions. Bulky substrates wer
- Zhao, Yiming,Van Nguyen, Huy,Male, Louise,Craven, Philip,Buckley, Benjamin R.,Fossey, John S.
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supporting information
p. 4224 - 4241
(2018/10/25)
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- Design, synthesis, and structure-activity relationships of novel imidazo[4,5-c]pyridine derivatives as potent non-nucleoside inhibitors of hepatitis C virus NS5B
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The hepatitis C virus (HCV) NS5B polymerase is an attractive target for the development of novel and selective inhibitors of HCV replication. In this paper, the design, synthesis, and preliminary SAR studies of novel inhibitors of HCV NS5B polymerase based on the structure of tegobuvir have been described. The efforts to optimize the antiviral potency and reduce the treatment side effects with respect to genotype 1b resulted in the discovery of compound 3, which exhibited an EC50 of 1.163 nM and a CC50 >200 nM in a cell-based HCV replicon system assay. Additionally, testing for inhibition of the hERG channel showed a marked improvement over tegobuvir and the pharmacokinetic properties of compound 3 indicated that it was worthy of further investigation as a non-nucleoside inhibitor of HCV NS5B polymerase.
- Liu, Moyi,Xu, Qiaoling,Guo, Su,Zuo, Ruixi,Hong, Yue,Luo, Yong,Li, Yingxiu,Gong, Ping,Liu, Yajing
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p. 2621 - 2631
(2018/04/30)
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- Chemoselective triazole-phosphonamidate conjugates suitable for photorelease
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Herein, we describe a new method for the conjugation of azide-containing target compounds that can be readily released as amines by irradiation with near UV light. This concept is based on a two-step protocol employing the chemoselective CuAAC and Staudinger-phosphonite reactions to deliver photo-cleavable phosphonamidate conjugates in high yields starting from 2-nitrobenzyl substituted phosphonites.
- Siebertz, Kristina D.,Hackenberger, Christian P. R.
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supporting information
p. 763 - 766
(2018/02/06)
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- Thermal azide-Alkene cycloaddition reactions: straightforward multi-gram access to Δ2-1,2,3-Triazolines in deep eutectic solvents
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The multi-gram synthesis of a wide range of 1,2,3-Triazolines via azide-Alkene cycloaddition reactions in a Deep Eutectic Solvent (DES) is reported. The role of DES in this transformation as well as the origin of the full product distribution was studied with an experimental/computational-DFT approach.
- Sebest, Filip,Casarrubios, Luis,Rzepa, Henry S.,White, Andrew J. P.,Díez-González, Silvia
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supporting information
p. 4023 - 4035
(2018/09/11)
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- Synthesis method for aryl azide compound
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The invention discloses a synthesis method for an aryl azide compound. The synthesis method includes the steps of: adding an iodo-aryl compound, sodium azide, 1,8-diazabicyclo[5.4.0]undecane-7-ene and a catalyst into a reaction container filled with a solvent, performing a stirring reaction to the reaction mixture at 60-105 DEG C with TLC tracing detection until the reaction is completed, adding ammonia water to the reaction mixture, extracting the reaction mixture for 3 times by ethyl acetate, washing the reaction mixture for 1 time by saturated salt water, drying an organic phase, performing suction filtration and spinning solvent removal, and performing column chromatographic purification to obtain a target product. The method employs easy-to-obtained raw materials and has wide selection range of copper source of the catalyst, has mild reaction condition, simple operation and high yield.
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Paragraph 0008; 0011; 0012; 0013; 0014; 0015
(2017/08/28)
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