- Mutagenicity of alkyl azides
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Alkyl azides showed mutagenicity for S. typhimurium TA100 strain with S9 mix. However, no significant activity was observed for TA98 either with or without S9 mix or for TA100 without S9 mix. On the other hand, 3-azido-1,2- propanediol showed the enantios
- Matsumura,Shiozawa,Matsushita,Terao
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- Measurement and correlation of the solubility of (1-benzyl-1H-1,2,3-triazole-4-yl)methanol in water and alcohols at temperatures from 292.15 K to 310.15 K
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The solubilities of (1-benzyl-1H-1,2,3-triazole-4-yl)methanol (BTZM) in water, methanol, ethanol, n-propanol, isopropanol, and n-butanol were measured at temperatures ranging from 292.15 K to 310.15 K by a dynamic method under normal atmospheric pressure. The results showed that it increased with the increasing temperature and the order of solvents was: Order: Methanol > ethanol > n-propanol > n-butanol > isopropanol > water except three points. The solubility data were correlated with the Van't Hoff equation, modified Apelblat equation, and λh equation. The average relative deviations (ARD) were 1.87%, 1.53%, and 1.71%, and the root-mean-square-deviations (RMSD) were 2.37 × 10-2, 1.51 × 10-2, and 2.12 × 10-2, respectively. It was found that the modified Apelblat equation gave the best correlation results. Furthermore, the dissolution enthalpy of BTZM was calculated by the modified Apelblat equation.
- Li, Huiping,Liang, Shuqin,Li, Huiying,Shen, Le,Li, Huanxin,Mao, Zhendong
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- Click generated o-Cresolphthalein linked 1,2,3-triazole derivative for selective Pb(II) ion recognition
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Present report describes the “turn-on” absorbance response of a molecular assembly o-Cresolphthalein appended 1,4-disubstituted 1,2,3-triazole (o-CPT) on complexation with Pb(II) ions. Copper (I) catalyzed alkyne-azide cycloaddition reaction, a highly versatile and stereoselective approach to stitch diverse structural units has been employed to generate the designed receptor that has been successfully characterized through IR, NMR (1H, 13C) and mass spectroscopic techniques. UV-Visible absorption spectral behavior of o-CPT was examined with a series of metal ions (Mn (II), Ce (III), Hg (II), Ni (II), Pb (II), Zn (II), Fe (II), Cr (III), Co (II) and Na (I)) in acetonitrile-water (4:1, v/v) solution and the results obtained have marked out the sensitivity of the designed probe exclusively towards Pb(II) ions with a measured detection limit of 13 μM at 2:1 stoichiometry of o-CPT:Pb(II) complex.
- Saini, Parveen,Singh, Gurjaspreet,Kaur, Gurpreet,Singh, Jandeep,Singh, Harminder
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- Alkylphosphinites as Synthons for Stabilized Carbocations
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We present a new acid-free method for the generation of carbocations based on a redox condensation reaction that enables SN1 reactions with a variety of nucleophiles. We utilize readily synthesized phosphinites that are activated by diisopropyl azodicarboxylate to form betaine structures that collapse upon adding a pronucleophile, thereby yielding reactive carbocation intermediates. We also employ this approach for the alkylation of some bioactive molecules.
- Ochmann, Lukas,Kessler, Mika L.,Schreiner, Peter R.
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supporting information
p. 1460 - 1464
(2022/03/01)
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- Combinatorial synthesis of new fluorescent scaffolds using click chemistry
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Azides and acetylenes are bio-orthogonal functional groups that can be readily coupled using copper(I)- or ruthenium(II)- catalyzed 1,3-dipolar cycloaddition reactions. Using non-fluorescent aromatic azides and aromatic acetylenes, covering a range of electron rich and poor building blocks, the Huisgen cycloaddition afford 1,4-disubstituted or 1,5-disubstituted 1,2,3-triazoles. Using a combinatorial approach by running reaction in parallel in polypropylene 96-well plates we discovered several new fluorescent 1,2,3-triazoles scaffolds. These compounds show diverse interactions with biomolecules that could find applications in biology in, for example, fluorescence microscopy or biomolecule quantification.
- Cleemann, Felix,Karuso, Peter,Kum-Cheung, Wendy Loa
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supporting information
(2021/12/08)
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- ‘Quick CuAAC’ Chemistry for Hg(II) and Mn(II) ion sensing via 9H-carbazole derivatives
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The synthesis of 1,2,3-triazole merged 9H–carbazole derivative is being reported with excellent yield but drastic reduction in the reaction time. The 1,2,3-triazole linker has been synthesized under thermal conditions within 20 min and yield of more than 90%, using Cu(I) as catalyst. Using UV–Vis spectral technique, the alkyne product displayed excellent detection capability towards Hg(II) and Mn(II) ions in methanol with the detection limit as low as 20 μM and 10 μM, respectively, whereas the triazolyl product can efficiently sense Cu(II) ions.
- Kaur, Gurpreet,Rani, Alisha,Saini, Parveen,Singh, Gurjaspreet,Singh, Harminder,Singh, Jandeep,Sushma
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- Discovery of triazolyl thalidomide derivatives as anti-fibrosis agents
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Fibrosis with excessive accumulation of extracellular matrix (ECM) often causes progressive organ dysfunction and results in many inflammatory and metabolic diseases, including systemic sclerosis, pulmonary fibrosis, advanced liver disease and advanced kidney disease. The store-operated calcium entry (SOCE) pathway and the related signaling pathway were both found to be the important routes for fibrogenesis. Our aim in this study was to discover novel compounds to inhibit fibrogenesis. A number of triazolyl thalidomide derivatives were synthesized and evaluated for their anti-fibrosis activities. Compounds 7b-e, 8c-d, 10a-b and 10e inhibited intracellular Ca2+ activation and showed no cytotoxicity. Among them, 6-{4-[(3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}hexanoic acid (10e) with the most potent inhibitory effect was chosen for further examination. The results revealed that compound 10e, a SOCE inhibitor, reversed the migratory ability of TGF-β1-induced myofibroblasts, dedifferentiated myofibroblasts to fibroblasts due to cytoskeleton remodeling, and restrained myofibroblast activation by targeting Orai1 and TGF-β1/SMAD2/3 signaling pathways. The in silico study indicated that compound 10e, with the appropriate lipophilic carbon chain and carboxylic acid, showed a good drug-likeness model score. Conclusively, the SOCE inhibitor, compound 10e, is used as a promising lead compound for the development of a new treatment for fibrosis. This journal is
- Tang, Kai-Wei,Hsu, Wen-Li,Chen, Cheng-Ru,Tsai, Ming-Hsien,Yen, Chia-Jung,Tseng, Chih-Hua
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p. 3589 - 3599
(2021/03/03)
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- Synthesis and muscarinic acetylcholine receptor (mAChR) antagonist activity of substituted piperazine-triazoles
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This study describes synthesis of a series of piperazine-triazole derivatives and their ex vivo evaluation for preliminary muscarinic acetylcholine receptor (mAChR) blocking activity on rat ileum model. A molecule based on benzonitrile piperazine triazole scaffold showed good tissue relaxation and blocking of neurotransmitter ACh in the ex vivo experiment. Graphic abstract: [Figure not available: see fulltext.]
- Acharya, Badri Narayan,Ghorpade, RamaRao,Singh, Kshetra Pal,Kumar, Deo,Nayak, Sabita
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p. 357 - 366
(2021/03/16)
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- Synthesis, characterization, and photochromism study of two spiropyran molecules with a terminal alkynyl functional group and their new 1,2,3-triazoline-containing derivatives
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The spiropyran derivatives are known for their good photochromic properties. These photochromic compounds are isomerized between two forms; merocyanine is the open-ring form and spiropyran is the closed-ring form. In this work, two spiropyran derivatives (compounds 1 and 2) with the N-alkynyl functional group are prepared. The click reactions of these spiropyran derivatives with 1-azido-4-nitrobenzene and (azidomethyl)benzene are studied. For this purpose, 3,3-dimethyl-2-methylene-1-prop-2-ynyl-2,3-dihydro-1H-indole is synthesized, which is then reacted with 3- and 5-nitrosalicylaldehyde. The FT-IR, 1H-NMR, and 13C-NMR spectra of the reaction products are used for their characterization. The solutions of the products in methanol are prepared, and their UV–visible spectra are investigated. The darkening of the crystals of compound 1 upon exposure to the UV irradiation indicates that the spiro C–O bond in this compound is weaker than that in compound 2, which is due to the presence of the nitro group in the para position relative to this bond, and consequently, the stabilization of the open-ring form.
- Mahdavian, Ali Reza,Nasr-Isfahani, Hossein,Notash, Behrouz,Sepehr, Zeinalabedin
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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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- Synthesis, Docking, and Biological activities of novel Metacetamol embedded [1,2,3]-triazole derivatives
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ERα controls the breast tissue development and progression of breast cancer. In our search for novel compounds to target Estrogen Receptor Alpha Ligand-Binding Domain, we identified “N-(3-((1H-1,2,3-triazol-4-yl)methoxy)phenyl)acetamide” derivatives as lead compounds. The Docking studies indicated good docking score for Metacetamol derivatives when docked into the 1XP6. A series of metacetamol derivatives have been synthesized, characterized and evaluated for cytotoxicity, anti bacterial and anti oxidant activities. Among the tested twelve hybrid compounds, “7a, 7g, 7h and 7i” derivatives showed promising cytotoxicity with IC50 value of 50 value of 30 μM, whereas Compounds “7a, 7b, 7c, 7d, 7g, 7j, 7k and 7l” showed moderate anti bacterial activity with the MIC value of 300 μM.
- Battu, Satyanarayana,Joolakanti, Hima Bindhu,Kamepalli, Ramanjaneyulu,Miryala, Jeevanreddy
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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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- NOVEL DIBENZOOXAPHOSPHININE OXIDE DERIVATIVE COMPOUNDS AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING DEGENERATIVE DISEASE COMPRISING THE SAME AS AN ACTIVE INGREDIENT
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The present invention relates to a novel dibenzooxininin oxide derivative compound having various nitrogen-containing substituents introduced at 6-position of a dibenzooxaphosphorin oxide mononuclear, and to the use thereof. The present invention relates to a pharmaceutical composition for preventing or treating degenerative diseases and a health supplement food composition for preventing or treating degenerative diseases, comprising the dibenzooxaphosphorin oxide derivative compound of the present invention.
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Paragraph 0113-0116
(2021/03/23)
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- Synthesis, biological evaluation and molecular docking studies of novel 1,2,3-triazole-quinazolines as antiproliferative agents displaying ERK inhibitory activity
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ERK1/2 inhibitors have attracted special attention concerning the ability of circumventing cases of innate or log-term acquired resistance to RAF and MEK kinase inhibitors. Based on the 4-aminoquinazoline pharmacophore of kinases, herein we describe the synthesis of 4-aminoquinazoline derivatives bearing a 1,2,3-triazole stable core to bridge different aromatic and heterocyclic rings using copper-catalysed azide-alkyne cycloaddition reaction (CuAAC) as a Click Chemistry strategy. The initial screening of twelve derivatives in tumoral cells (CAL-27, HN13, HGC-27, and BT-20) revealed that the most active in BT-20 cells (25a, IC50 24.6 μM and a SI of 3.25) contains a more polar side chain (sulfone). Furthermore, compound 25a promoted a significant release of lactate dehydrogenase (LDH), suggesting the induction of cell death by necrosis. In addition, this compound induced G0/G1 stalling in BT-20 cells, which was accompanied by a decrease in the S phase. Western blot analysis of the levels of p-STAT3, p-ERK, PARP, p53 and cleaved caspase-3 revealed p-ERK1/2 and p-STA3 were drastically decreased in BT-20 cells under 25a incubation, suggesting the involvement of these two kinases in the mechanisms underlying 25a-induced cell cycle arrest, besides loss of proliferation and viability of the breast cancer cell. Molecular docking simulations using the ERK-ulixertinib crystallographic complex showed compound 25a could potentially compete with ATP for binding to ERK in a slightly higher affinity than the reference ERK1/2 inhibitor. Further in silico analyses showed comparable toxicity and pharmacokinetic profiles for compound 25a in relation to ulixertinib.
- Nunes, Paulo Sérgio Gon?alves,da Silva, Gabriel,Nascimento, Sofia,Mantoani, Susimaire Pedersoli,de Andrade, Peterson,Bernardes, Emerson Soares,Kawano, Daniel Fábio,Leopoldino, Andreia Machado,Carvalho, Ivone
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supporting information
(2021/05/26)
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- N-pyridine-4-yl-benzamide Cdc37 inhibitor as well as derivative and application thereof
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The invention discloses an N-pyridine-4-yl-benzamide Cdc37 inhibitor with a structure as shown in a general formula (I) as well as a derivative and application thereof. The compound disclosed by the invention can inhibit Cdc37 protein and downstream custo
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Paragraph 0078; 0087-0089
(2021/05/19)
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- Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis
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Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO3H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN3 to benzylic azides and 1,2,3-triazoles in EtOH (95%), respectively, avoiding the use of risky DMF and improving the separation processes of the products.
- Bai, Rongxian,Gao, Feng,Gu, Yanlong,Li, Minghao
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p. 7499 - 7505
(2021/10/12)
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- Regioselective reduction of 1h-1,2,3-triazole diesters
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Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding.
- Butler, Christopher R.,Bendesky, Justin,Schoffstall, Allen Milton
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- Predicting the catalytic activity of azolium-based halogen bond donors: an experimentally-verified theoretical study
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This report demonstrates the successful application of electrostatic surface potential distribution analysis for evaluating the relative catalytic activity of a series of azolium-based halogen bond donors. A strong correlation (R2> 0.97) was observed between the positive electrostatic potential of the σ-hole on the halogen atom and the Gibbs free energy of activation of the model reactions (i.e., halogen abstraction and carbonyl activation). The predictive ability of the applied approach was confirmed experimentally. It was also determined that the catalytic activity of azolium-based halogen bond donors was generally governed by the structure of the azolium cycle, whereas the substituents on the heterocycle had a limited impact on the activity. Ultimately, this study highlighted four of the most promising azolium halogen bond donors, which are expected to exhibit high catalytic activity.
- Bolotin, Dmitrii S.,Il'in, Mikhail V.,Novikov, Alexander S.,Suslonov, Vitalii V.,Sysoeva, Alexandra A.
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supporting information
p. 7611 - 7620
(2021/09/22)
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- Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols
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We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.
- Chen, Yuming,He, Ru,Song, Hongjian,Yu, Guoqing,Li, Chenglin,Liu, Yuxiu,Wang, Qingmin
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p. 1179 - 1183
(2021/02/01)
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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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- Design, synthesis and photoluminescent studies of new 1,5-benzodiazepines derivatives: Towards new ESIPT compounds
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A series of novel N1-triazolo-4-(2-hydroxyphenyl)-1,5-benzodiazepin-2-ones 7a-e and N5-triazolo-4-(2-acetoxyphenyl)-1,5-benzodiazepin-2-ones 8a-e were designed and synthesized in good yields via a Cu(I) catalyzed 1,3-dipolar alkyne-azide coupling reaction (CuAAC) between the N1- and N5-propargyl-1,5-benzodiazepines 2 and 5 respectively and various arylazides 6a-e. Photophysical properties were investigated for all the obtained triazolo-benzodiazepine hybrids by mean of absorption and fluorescence spectral techniques. Thus, a fluorescent emission was detected for the derivatives 7a-e in aggregated state. On another hand, the O-acetylated derivatives 8a-e were found to be not emissive. Finally, we have chosen a model reaction to demonstrate that upon deprotecting the -OAc group in the N1, N5-disubstituted benzodiazepine 8d a moderate fluorescence reappeared in the obtained product 9d proving that an ESIPT process can take place as long as the hydroxyl group remains free, allowing the OH/C[dbnd]O proton transfer to occur. A computational study of compounds 7e and 9d in vacuo provide further details and arguments to rationalize the fluorescence of these compounds in aqueous mixtures.
- Ismail, Chiraz,Mtiraoui, Hasan,Winum, Jean-Yves,Msaddek, Moncef,Gharbi, Rafik
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- Synthesis, Characterization and Cytotoxic Activity of some New 1,2,3-Triazole, Oxadiazole and Aza- β-lactam Derivatives
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A series of 1,2,3-triazole, oxadiazole and aza-β-lactam derivatives were synthesized through consecutive reaction began from o-(N-propargyl) sulfonamido benzoic acid (1a). The reaction of (1a) with absolute ethanol in the presence of concentrated H2SO4 resulted in the formation of ester derivative (2a). The product of the previous reaction was reacted with 80% hydrazine hydrate to prepare benzohydrazide derivative (3a). 1,3,4-oxadiazole compound (4a) was obtained by condensation of compound (3a) with CS2 in presence KOH. Compound (3a) react with Phenyl isocyanates to give Carboxamide derivative (5a), that Condensation either with 2,4-dimethoxybenzaldhyde and p-hydroxybenzaldehyde to prepare the Schiff bases (6a-b). The cycloaddotion of Schiff-bases (6a-b) with phenyl isocyanate gave aza-β-lactams (7a-b). Benzamide derivatives (8a-c) were prepared via the reaction of compound (1a) with aniline derivatives, such as (p-toluidine, o-nitroaniline and m-nitroaniline). In a regioselective reaction 1,4-disubstituted-1,2,3-triazole derivative (9a-j) were synthesized via the click reaction of compounds 4a,5a and (8a-c) with benzyl azide and p-bromobenzyl azide. The compounds were identified using the spectral methods shown in the work. Cytotoxic effects of some final prepared compounds were studied in one cultured cellular models (MCF7 cell line) breast cancer (at various concentrations) by MTT assay, compound (9j) showed the better cytotoxic activity among the tested compounds.
- Abdul Qader, Kany A.,Farhan, Muthanna S.,Naser, Ahmed W.,Salih, Sabah J.
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p. 2350 - 2360
(2020/12/21)
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- Design and synthesis of C-ring quinoxaline-substituted sinomenine 1,2,3-triazole derivatives via click reactions
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The synthesis of C-ring quinoxaline-substituted sinomenine 1,2,3-triazole derivatives at the 4-OH via click reactions is accomplished, and a total of 16 novel sinomenine double N-heterocyclic derivatives are obtained in 74%–95% yields. The C-ring is first transformed into a 1,2-diketone structure under the action of hydrochloric acid, and then reacted with o-phenylenediamine to obtain a C-ring quinoxaline-substituted structure. The 4-OH of sinomenine reacts with chloropropyne to give an alkynyl sinomenine, and then reacts with sodium azide and various benzyl chlorides to give the target compounds. All the synthesized derivatives are characterized by Fourier-transform infrared spectrometry, high resolution mass spectrometry, 1H NMR, and 13C NMR spectroscopy.
- Chen, Xia,Dong, Ling,Gu, Chengwen,Jin, Jie,Lu, Tong,Pan, Hongmei,Tao, Naili,Wang, Ao,Wu, Xuedan,Zhang, Kehua
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p. 699 - 704
(2020/06/03)
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- A Nanosized Propeller-like Polyoxometalate-linked Copper(I)-Resorcin[4]arene for Efficient Catalysis
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The design and assembly of polyoxometalate-resorcin[4]arene-based metal-organic molecular materials are particularly attractive for their elegant structures and potential functions. By applying a newly designed resorcin[4]arene ligand (TPC4R-II), a copper(I)-coordinated polyoxometalate-based metal-organic molecular material, namely, [CuI6(Br)3(TPC4R-II)3(PMo12O40)]·8H2O (1), was rationally assembled. Three copper(I)-coordinated resorcin[4]arenes are held together by a central [PMo12O40]3- to yield a supramolecular propeller. 1 features efficient catalytic performances for oxidation desulfurization (ODS) and azide-alkyne cycloaddition (AAC) reactions. This work affords a feasible method for the nanosized polyoxometalate-based metal-resorcin[4]arene assemblies by well combinating two types of large composites as well as low coordination metal cations.
- Guo, Ting-Ting,Ma, Jian-Fang,Xiong, Yan-Ling,Yang, Jin,Yu, Ming-Yue
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p. 15402 - 15409
(2020/11/02)
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- Heterogeneous photocatalysis of azides: Extending nitrene photochemistry to longer wavelengths
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The photodecomposition of azides to generate nitrenes usually requires wavelengths in the 300 nm region. In this study, we show that this reaction can be readily performed in the UVA region (368 nm) when catalyzed by Pd-decorated TiO2. In aqueous medium the reaction leads to amines, with water acting as the H source; however, in non-protic and non-nucleophilic media, such as acetonitrile, nitrenes recombine to yield azo compounds, while azirine-mediated trapping occurs in the presence of nucleophiles. The heterogeneous process facilitates catalyst separation while showing great chemoselectivity and high yields.
- Argüello, Juan E.,Lanterna, Anabel E.,Lemir, Ignacio D.,Scaiano, Juan C.
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supporting information
p. 10239 - 10242
(2020/10/02)
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- Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization
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Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effectively rerouting our previously reported α-amination transform.
- Maulide, Nuno,Riomet, Margaux,Roller, Alexander,Zhang, Haoqi
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supporting information
(2020/03/24)
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- Discovery and Characterization of 1 H-1,2,3-Triazole Derivatives as Novel Prostanoid EP4 Receptor Antagonists for Cancer Immunotherapy
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The prostanoid EP4 receptor is one of the key receptors associated with inflammatory mediator PGE2-elicited immunosuppression in the tumor microenvironment. Blockade of EP4 signaling to enhance immunity-mediated tumor elimination has recently emerged as a promising strategy for cancer immunotherapy. In our efforts to discover novel subtype-selective EP4 antagonists, we designed and synthesized a class of 1H-1,2,3-triazole-based ligands that display low nanomolar antagonism activity toward the human EP4 receptor and excellent subtype selectivity. The most promising compound 59 exhibits single-digit nanomolar potency in the EP4 calcium flux and cAMP-response element reporter assays and effectively suppresses the expression of multiple immunosuppression-related genes in macrophage cells. On the basis of its favorable ADMET properties, compound 59 was chosen for further in vivo biological evaluation. Oral administration of compound 59 significantly inhibited tumor growth in the mouse CT26 colon carcinoma model accompanied by enhanced infiltration of cytotoxic T lymphocytes in the tumor tissue.
- Yang, Jun-Jie,Yu, Wei-Wei,Hu, Long-Long,Liu, Wen-Juan,Lin, Xian-Hua,Wang, Wei,Zhang, Qiansen,Wang, Pei-Li,Tang, Shuo-Wen,Wang, Xin,Liu, Mingyao,Lu, Weiqiang,Zhang, Han-Kun
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p. 569 - 590
(2020/02/05)
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- Cycloaddition Reactions of Azides and Electron-Deficient Alkenes in Deep Eutectic Solvents: Pyrazolines, Aziridines and Other Surprises
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The reaction of organic azides and electron-deficient alkenes was investigated in a deep eutectic solvents. A series of highly substituted 2-pyrazolines was successfully isolated and their formation rationalised by DFT calculations. The critical effect of substitution was also explored; even relatively small changes in the cycloaddition partners led to completely different reaction outcomes and triazolines, triazoles or enaminones can be formed as major products depending on the alkene employed. (Figure presented.).
- Casarrubios, Luis,Díez-González, Silvia,Lachhani, Kushal,Pimpasri, Chaleena,Rzepa, Henry S.,Sebest, Filip,White, Andrew J. P.
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supporting information
(2020/05/19)
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- Rhenium Complexes of Pyridyl-Mesoionic Carbenes: Photochemical Properties and Electrocatalytic CO2 Reduction
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Mesoionic carbenes have found wide use as components of homogeneous catalysts. Recent discoveries have, however, shown that metal complexes of such ligands also have huge potential in photochemical research and in the activation of small molecules. We pre
- Berlinguette, Curtis P.,Brown, Christopher M.,Fiedler, Jan,Klein, Johannes,Parlane, Fraser G. L.,Sarkar, Biprajit,Siewert, Inke,Stein, Felix,Suntrup, Lisa,Wilting, Alexander
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- Copper(i) complexes bearing mesoionic carbene ligands: Influencing the activity in catalytic halo-click reactions
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Metal complexes of mesoionic carbene (MIC) ligands are known to catalyze a variety of chemical transformations. In this contribution, we report on the synthesis of a dicationic dicopper(i) complex containing a di-MIC ligand. Two routes are presented for the synthesis of the dicopper complex: Ag-mediated transmetalation and direct deprotonation. For the Ag-mediated transmetalation route, the detection and isolation of several Ag-containing intermediates that are relevant for the final formation of the aforementioned dicopper complex are reported. We then investigate a series of copper(i) complexes based on MIC ligands as precatalysts for the azide halo-alkyne (Click) cycloaddition reaction. In a comparative study, three different halide-containing (I, Br, Cl) substrates have been investigated with different catalysts to survey the behaviour for mono/di-copper-MIC complexes as well as neutral, mono- and di-cationic complexes. The cationic complexes proved to have superior activities compared to the neutral species. These are the first reports on the use of Cu-MIC complexes as precatalysts for the halo-Click reaction.
- Beerhues, Julia,Etzold, Oliver,Sarkar, Biprajit,Suntrup, Lisa
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supporting information
p. 15504 - 15510
(2020/11/18)
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- Synthesis and in vitro cytotoxicity and antibacterial activity of novel1,2,3-triazol-5-yl-phosphonates
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Novel1,2,3-triazol-5-yl-phosphonates were prepared by the copper(I)-catalyzed domino reaction of phenylacetylene, organic azides and dialkyl phosphites. The process was optimized on the synthesis of the dibutyl (1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)phosphonate in respect of the catalyst, the base and the solvent, as well as of the reaction parameters (molar ratio of the starting materials, atmosphere, temperature and reaction time). The method elaborated could be applied to a range of organic azides and dialkyl phosphites, which confirmed the large scope and the functional group tolerance. The in vitro cytotoxicity on different cell lines and the antibacterial activity of the synthesized1,2,3-triazol-5-yl-phosphonates was explored. According to the IC50 values determined, only modest antibacterial effect was detected, while some derivatives showed moderate activity against human promyelocytic leukemia HL-60 cells.
- Bálint, Erika,Hackler, László,Kari, Beáta,Puskás, László G.,Szabó, Pál Tamás,Tóth, Emese,Tripolszky, Anna
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- Design and synthesis of substituted (1-(benzyl)-1: H -1,2,3-triazol-4-yl)(piperazin-1-yl)methanone conjugates: Study on their apoptosis inducing ability and tubulin polymerization inhibition
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A library of substituted (1-(benzyl)-1H-1,2,3-triazol-4-yl)(piperazin-1-yl)methanone derivatives were designed, synthesized and screened for their in vitro cytotoxic activity against BT-474, HeLa, MCF-7, NCI-H460 and HaCaT cells by employing 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among all the synthesized analogues, compound 10ec displayed the highest cytotoxicity with the IC50 value of 0.99 ± 0.01 μM towards BT-474 cancer cell line. The target compound (10ec) was also evaluated for its tubulin polymerization inhibition study. Detailed biological studies such as acridine orange/ethidium bromide (AO/EB), DAPI and annexin V-FITC/propidium iodide staining assay suggested that compound 10ec induced the apoptosis of BT-474 cells. The clonogenic assay revealed that the inhibition of colony formation in BT-474 cells by 10ec in concentration-dependent manner. Moreover, the flow cytometric analysis revealed that 10ec induced apoptosis via cell cycle arrest at the sub-G1 and G2/M phase. In silico studies of sulfonyl piperazine-integrated triazole conjugates unveil that they possess drug-like properties. According to the molecular modelling studies, compound 10ec binds to the colchicine binding site of the tubulin.
- Alvala, Mallika,Babu, Bathini Nagendra,Devi, Ganthala Parimala,Godugu, Chandraiah,Manasa, Kesari Lakshmi,Nagesh, Narayana,Sigalapalli, Dilep Kumar,Thatikonda, Sowjanya,Vuppaladadium, Sowmya
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p. 1295 - 1302
(2020/12/01)
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- Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides
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The boom in growth of 1,4-disubstituted triazole products, in particular, since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the CuI-catalyzed azide–alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click-inspired protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1-substituted-1,2,3-triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts.
- Giel, Marie-Claire,Smedley, Christopher J.,Mackie, Emily R. R.,Guo, Taijie,Dong, Jiajia,Soares da Costa, Tatiana P.,Moses, John E.
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supporting information
p. 1181 - 1186
(2019/12/11)
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- Novel 4-(1H-1,2,3-triazol-4-yl)methoxy)cinnolines as potent antibacterial agents: Synthesis and molecular docking study
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A new series of cinnoline-1,2,3-triazole derivatives were designed and synthesized by adopting Cu(1) catalyzed regeoselective1,3-dipolar cycloaddition reaction of terminal alkyne and azide. The in vitro antibacterial activity of all these compounds revealed that compounds 9d, 10a, 10b, and 10c are more potent antibacterial agents. Among the series, compound 4-(3-(4-((cinnolin-4-yloxy)methyl)-1H-1,2,3-triazol-1-yl)propyl)morpholine (10b) exhibited the most potent antibacterial activity against all tested gram-positive and gram-negative bacterial strains. Furthermore, molecular docking studies were also performed to understand the binding interactions of the most active analogs 9d, 10a, 10b, and 10c with Elastase of Pseudomonas aeruginosa (PDB: 1U4G). The results indicated that these classes of compounds have potential antibacterial activity, especially the compound 10b may serve as a promising antibacterial lead compound that could be further optimized for the further development of antibacterial drugs.
- Boda, Sathish Kumar,Bommagani, Mohan Babu,Chitneni, Prasad Rao,Mokenapelli, Sudhakar,Yerrabelli, Jayaprakash Rao
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supporting information
(2020/03/04)
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- Novel insights on saccharin- and acesulfame-based carbonic anhydrase inhibitors: design, synthesis, modelling investigations and biological activity evaluation
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A large library of saccharin and acesulfame derivatives has been synthesised and evaluated against four isoforms of human carbonic anhydrase, the two off-targets hCA I/II and the tumour related isoforms hCA IX/XII. Different strategies of scaffold modification have been attempted on both saccharin as well as acesulfame core leading to the obtainment of 60 compounds. Some of them exhibited inhibitory activity in the nanomolar range, albeit some of the performed changes led to either micromolar activity or to its absence, against hCA IX/XII. Molecular modelling studies focused the attention on the binding mode of these compounds to the enzyme. The proposed inhibition mechanism is the anchoring to zinc-bound water molecule. Docking studies along with molecular dynamics also underlined the importance of the compounds flexibility (e.g. achieved through the insertion of methylene group) which favoured potent and selective hCA inhibition.
- Guglielmi, Paolo,Rotondi, Giulia,Secci, Daniela,Angeli, Andrea,Chimenti, Paola,Nocentini, Alessio,Bonardi, Alessandro,Gratteri, Paola,Carradori, Simone,Supuran, Claudiu T.
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p. 1891 - 1905
(2020/10/06)
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- PEG-DIL-based MnCl42?: A novel phase transfer catalyst for nucleophilic substitution reactions of benzyl halides
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Poly(ethylene glycol) dicationic ionic liquid-based MnCl42? was prepared by nucleophilic substitution of poly(ethylene glycol) dichloride with methylimidazole followed by reaction with MnCl2. The structural properties of the catalyst were systematically investigated using Fourier transform infrared, UV–visible and Raman spectra and thermogravimetric analysis. The application of this catalyst allows the synthesis of a variety of benzyl thiocyanates and azides in high yield under reflux conditions in water. The main advantages of this method are its easy nature, rapidity, environmental benignity and high yields.
- Goodajdar, Bijan Mombeni,Akbari, Farideh,Davarpanah, Jamal
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- Luminescent iridium(iii) complexes of N-heterocyclic carbene ligands prepared using the 'click reaction'
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A series of imidazolium salt, N-heterocyclic carbene (NHC) ligand precursors, combined with 1,2,3-triazoles were synthesized using the Cu(i) catalyzed azide-alkyne cycloaddition 'click reaction'. These pro-ligands were prepared from imidazolium molecules that were functionalized with either a terminal alkyne or azide group. Methylation of the triazole unit with methyl iodide produced a series of imidazolium/triazolium NHC pro-ligands. From these pro-ligands a family of luminescent Ir(iii) complexes of the general form [Ir(ppy)2(C^N)]+ or [Ir(ppy)2(C-C)]+ (where ppy is 2-phenylpyridine and C-N represents a bidentate imidazolylidene/triazole ligand and C-C represents a bidentate imidazolylidene/triazolylidene ligand) were prepared. The electrochemical, photophysical and electrochemiluminescence properties of the complexes have been evaluated and a preliminary study of two of these compounds as luminescent probes for cell imaging studies was conducted in A549 human lung adenocarcinoma basal epithelial cells. Co-localisation studies with the commercial dye MitoTracker CMXRos were consistent with mitochondrial uptake for these compounds.
- Karmis, Rebecca E.,Carrara, Serena,Baxter, Amy A.,Hogan, Conor F.,Hulett, Mark D.,Barnard, Peter J.
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p. 9998 - 10010
(2019/07/15)
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- Polyoxometalate-Bridged Cu(I)- And Ag(I)-Thiacalix[4]arene Dimers for Heterogeneous Catalytic Oxidative Desulfurization and Azide-Alkyne "click" Reaction
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Two remarkable polyoxometalate-bridged Cu(I)- and Ag(I)-thiacalix[4]arene dimers, namely, [Cu4(SiW12O40)(L)2(DMF)2]·2EtOH·DMF (1-Cu) and [Ag4(PMo12O40)(L)2]·OH (1-Ag), were prepared by using a new thiacalix[4]arene, metal cation and polyoxometalate (L = tetra[2-(ethylthio)-1-methyl-1H-imidazole]-thiacalix[4]arene). In 1-Cu and 1-Ag, two thiacalix[4]arenes were linked together by one [SiW12O40]4- or [PMo12O40]3- anion via two metal cations to give a molecular dimer. Further, adjacent dimers were extended into a high-dimensional supramolecular architecture through hydrogen bonds. Markedly, these molecular dimers are exceedingly stable in organic solvents and then were employed as efficient catalysts for catalytic oxidation desulfurization as well as the azide-alkyne "click" reaction.
- Yu, Ming-Yue,Guo, Ting-Ting,Shi, Xiao-Chuan,Yang, Jin,Xu, Xianxiu,Ma, Jian-Fang,Yu, Zhen-Tao
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supporting information
p. 11010 - 11019
(2019/08/26)
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- Design, synthesis, and anti-bacterial evaluation of triazolyl-pterostilbene derivatives
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Staphylococcus aureus resistance to current antibiotics has become the greatest global challenge facing public health. The development of new antimicrobial agents is urgent and important and is needed to provide additional therapeutic options. In our previous study, we found out that pterostilbene exhibited potent antibacterial activity, especially against methicillin-resistant Staphylococcus aureus (MRSA). According to previous studies, 1,2,3-triazole, with the characteristic of increasing the interaction with the target readily and enhancing water solubility, were widely used in the approved anti-bacterial drugs. Therefore, these results attract our interest to use the structure of pterostilbene as a scaffold for the hybrid 1,2,3-triazole moiety to develop a novel anti-MRSA infection agent. In this study, we demonstrated the design and synthesis of a series of triazolylpterostilbene derivatives. Among these compounds, compound 4d exhibited the most potent anti-MRSA activity with a minimum inhibitory concentration (MIC) value of 1.2-2.4 μg/mL and a minimum bactericidal concentration (MBC) value of 19.5-39 μg/mL. The structure-activity relationship and antibacterial mechanism were investigated in this study. Molecular docking studies were carried out to verify and rationalize the biological results. In this study, the results confirmed that our design could successfully increase the inhibitory activity and specificity against MRSA. Compound 4d could be used as a candidate for anti-bacterial agents and in depth vivo studies should be further investigated.
- Tang, Kai-Wei,Yang, Shih-Chun,Tseng, Chih-Hua
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- Carcarinic acid-1, 2, 3- based triazole compound as well as preparation method and application thereof (by machine translation)
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The method comprises the following steps: firstly 1, 2, 3 - oxidizing and opening the carbon- carbon double bond of the, carcarinic acid into methylene to, obtain carcarinic acid (not shown, in the technical field of, organic 3 - synthesis), Wolf - Kishner - 1, 2, 3 - 1, 2, 3 - 1, 2, 3 - 3 . (by machine translation)
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Paragraph 0045-0047
(2019/12/25)
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- Synthesis of nerol derivatives containing a 1,2,3-triazole moiety and evaluation of their activities against cancer cell lines
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In the present investigation, a collection of twenty two nerol derivatives, containing 1,2,3-triazolic appendages, was synthesized and screened in vitro for their cytotoxic activity against HL60, Nalm6, and Jurkat human leukemia cells as well as against B16F10 (melanoma cell line). In most cases, derivatives were able to reduce cell viability. The most potent compound (Z)-4-(((3,7-dimethylocta-2,6-dien-1-yl)oxy)methyl)-1-(4-(trifluoromethoxy)benzyl)-1H-1,2,3 triazole showed antiproliferative activity against Jurkat cells and reduced B16F10 cell migration. Physicochemical properties of the compounds were calculated in order to evaluate their potential for drug development. Most of the evaluated physicochemical parameters seemed to be favorable for drug development. In addition, for a better understanding of the biological activity results, 3D quantitative structure-activity relationship (QSAR) studies were carried out. 3D-QSAR studies indicate that the anticancer activities observed for the cell lines HL60 and Jurkat may occur by a similar mechanism of action and the same was found for the Nalm6 and B16F10 cell lines.
- Teixeira, Róbson R.,Da Silva, Adalberto M.,Siqueira, Raoni P.,Gon?alves, Victor Hugo S.,Pereira, Higor S.,Ferreira, Rafaela S.,Costa, Adilson V.,de Melo, Eduardo B.,Paula, Fávero R.,Ferreira, Márcia M.C.,Bressan, Gustavo C.
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p. 541 - 561
(2019/08/26)
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- Synthesis of cinnamic acid derivatives and leishmanicidal activity against Leishmania braziliensis
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Leishmania braziliensis is one of the pathogenic agents of cutaneous and mucocutanoeous leishmaniasis. There are no validated vaccines to prevent the infection and the treatment relies on drugs that often present severe side effects, which justify the efforts to find new potential antileishmanial drugs. An alternative to promote the discovery of new drugs would be the association of different chemical groups of bioactive compounds. Here we describe the synthesis and bioactivity evaluation against L. braziliensis of cinnamic acid derivatives possessing isobenzofuranone and 1,2,3-triazole functionalities. We tested 25 compounds at 10 μM concentration against extracellular promastigotes and intracellular amastigotes during macrophage infection. Most compounds were more active against amastigotes than to promastigotes. The derivatives (E)-3-oxo-1,3-dihydroisobenzofuran-5-yl-(3,4,5-trimethoxy) cinnamate (5c), (1-(3,4-difluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl cinnamate (9g), and (1-(2-bromobenzyl)-1H-1,2,3-triazol-4-yl)methyl cinnamate (9l) were the most effective presenting over 80% toxicity on L. braziliensis amastigotes. While compound 5c is a cinnamate with an isobenzofuranone portion, 9g and 9l are triazolic cinnamic acid derivatives. The action of these compounds was comparable to amphotericin B used as positive control. Ultrastructural analysis revealed that 5c-treated parasites showed impaired cytokinesis and apoptosis triggering. Taken together, these results highlight the potential of cinnamic acid derivatives in development of novel anti-leishmanial drugs.
- Rodrigues, Michelle Peixoto,Tomaz, Deborah Campos,?ngelo de Souza, Luciana,Onofre, Thiago Souza,Aquiles de Menezes, Wemerson,Almeida-Silva, Juliana,Suarez-Fontes, Ana Márcia,Rogéria de Almeida, Márcia,Manoel da Silva, Adalberto,Bressan, Gustavo Costa,Vannier-Santos, Marcos André,Rangel Fietto, Juliana Lopes,Teixeira, Róbson Ricardo
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- Copper-catalyzed cascade click/nucleophilic substitution reaction to access fully substituted triazolyl-organosulfurs
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A novel cascade click/nucleophilic substitution reaction is developed to access 4-heterofunctionalized fully substituted triazolyl-organosulfurs using thiocyanates as both leaving groups and organosulfur precursors. This method features high regioselectivities and board substrate scope. 33 examples are shown to demonstrate the structural diversity through the synthesis of fully substituted triazolyl-organosulfurs including triazolyl-thiocyanates, triazolyl-sulfinylcyanides, triazolyl-thioethers, triazolyl-thiols and triazolyl-disulfides from internal thiocyanatoalkynes.
- Li, Ming,Dong, Kun,Zheng, Yubin,Song, Wangze
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supporting information
p. 9933 - 9941
(2019/12/06)
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- Palladium-Catalyzed Annulation of Aryltriazoles and Arylisoxazoles with Alkynes
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We developed herein a palladium-catalyzed annulation of aryltriazoles and arylisoxazoles with internal alkynes via C?H bond activation process. 4,5-disubstituted-3H-naphtho[1,2-d][1,2,3]triazoles and 4,5-disubstituted-naphtho[2,1-d]isoxazoles could be afforded in good yields, respectively. The starting materials are readily available and the scope and applications of this transformation were explored. The reaction offers a practical approach to naphthalene fused heterocycles. (Figure presented.).
- Yuan, Hairui,Wang, Min,Xu, Zhenghu,Gao, Hongyin
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supporting information
p. 4386 - 4392
(2019/08/12)
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- Controlling the Kinetics of Self-Reproducing Micelles by Catalyst Compartmentalization in a Biphasic System
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Compartmentalization of reactions is ubiquitous in biochemistry. Self-reproducing lipids are widely studied as chemical models of compartmentalized biological systems. Here, we explore the effect of catalyst location on copper-catalyzed azide-alkyne cycloadditions which drive the self-reproduction of micelles from phase-separated components. Tuning the hydrophilicity of the copper-ligand complex, so that hydro-phobic or -philic catalysts are used in combination with hydro-philic and -phobic coupling partners, provides a wide range of reactivity patterns. Analysis of the kinetic data shows that reactions with a hydrophobic catalyst are faster than with a hydrophilic catalyst. Diffusion-ordered spectroscopy experiments suggest compartmentalization of the hydrophobic catalyst inside micelles while the hydrophilic catalyst remains in the bulk aqueous phase. The autocatalytic effects observed can be tuned by varying reactant structure and coupling a hydrophilic alkyne and hydrophobic azide results in a more pronounced autocatalytic effect. We propose and test a model that rationalizes the observations in terms of the phase behavior of the reaction components and catalysts.
- Post, Elias A. J.,Fletcher, Stephen P.
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p. 2741 - 2755
(2019/02/26)
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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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- 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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- Green methodologies for copper(I)-catalyzed azide-alkyne cycloadditions: A comparative study
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Successful copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions may be achieved by several methods. In this paper, four synthetic protocols were performed for direct comparison of time required for the synthesis, yield, and purity of the 1H-1,
- Trujillo, Marissa,Hull-Crew, Clayton,Outlaw, Andrew,Stewart, Kevin,Taylor, Loren,George, Laura,Duensing, Allison,Tracey, Breanna,Schoffstall, Allen
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- Synthesis and biological evaluation of 1-benzyl-N-(2-(phenylamino)pyridin-3-yl)-1H-1,2,3-triazole-4-carboxamides as antimitotic agents
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A library of 1-benzyl-N-(2-(phenylamino)pyridin-3-yl)-1H-1,2,3-triazole-4-carboxamides (7a–al) have been designed, synthesized and screened for their anti-proliferative activity against some selected human cancer cell lines namely DU-145, A-549, MCF-7 and HeLa. Most of them have shown promising cytotoxicity against lung cancer cell line (A549), amongst them 7f was found to be the most potent anti-proliferative congener. Furthermore, 7f exhibited comparable tubulin polymerization inhibition (IC50 value 2.04 μM) to the standard E7010 (IC50 value 2.15 μM). Moreover, flow cytometric analysis revealed that this compound induced apoptosis via cell cycle arrest at G2/M phase in A549 cells. Induction of apoptosis was further observed by examining the mitochondrial membrane potential and was also confirmed by Hoechst staining as well as Annexin V-FITC assays. Furthermore, molecular docking studies indicated that compound 7f binds to the colchicine binding site of the β-tubulin. Thus, 7f exhibits anti-proliferative properties by inhibiting the tubulin polymerization through the binding at the colchicine active site and by induction of apoptosis.
- Prasad, Budaganaboyina,Lakshma Nayak,Srikanth,Baig, Mirza Feroz,Subba Reddy,Babu, Korrapati Suresh,Kamal, Ahmed
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p. 535 - 548
(2018/11/26)
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- One-pot sequential diprop-2-ynylation and cycloaddition: An efficient synthesis of novel N,N-bis(1,2,3-triazol-4-yl) methylarylamines starting from primary amines
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A facile, one-pot synthesis strategy for the tertiary arylamines bearing N,N-bis(1,2,3-triazol-4-yl)methyl structure has been developed by sequential diprop-2-ynylation of primary amines with propargyl bromide in the presence of calcium hydride in DMF and [3 + 2] “click” cycloaddition with organic azides promoted by cupric acetate in the mixed DMF-H2O media. This protocol provides some features, such as high efficiency and regioselectivity, easy operation, and moderate to good product yield (56–84%) with a wide substrate scope under mild conditions.
- He, Zhu-Jun,Wei, Mei-Hong,Zhang, Xiao-Lan,Chen, Jun-Min,Sheng, Shou-Ri
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p. 2760 - 2766
(2019/08/07)
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- 1,2,3-Triazolium-Based Cationic Amphipathic Peptoid Oligomers Mimicking Antimicrobial Helical Peptides
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Amphipathic cationic peptoids (N-substituted glycine oligomers) represent a promising class of antimicrobial peptide mimics. The aim of this study is to explore the potential of the triazolium group as a cationic moiety and helix inducer to develop potent antimicrobial helical peptoids. Herein we report the first solid-phase synthesis of peptoid oligomers incorporating 1,2,3-triazolium-type side chains and their evaluation against Escherichia coli, Enterococcus faecalis, and Staphylococcus aureus. Several triazolium-based oligomers, even of short length, selectively kill bacteria over mammalian cells. SEM visualization of S. aureus cells treated with a dodecamer and a hexamer reveals severe cell membrane damage and suggests that the longer oligomer acts by pore formation.
- Shyam, Radhe,Charbonnel, Nicolas,Job, Aurélie,Blavignac, Christelle,Forestier, Christiane,Taillefumier, Claude,Faure, Sophie
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supporting information
p. 1513 - 1516
(2018/07/31)
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- Design and synthesis of a magnetic hierarchical porous organic polymer: A new platform in heterogeneous phase-transfer catalysis
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Recyclable phase transfer catalysts containing magnetic nanoparticles (MNPs) have been known as a major trend towards sustainable catalysts. In this study, a novel class of magnetic porous polymer on the basis of calix[4]resorcinarene was synthesized starting from silica-coated Fe3O4 core-shell nanoparticles. This compound was found as an efficient phase transfer catalyst to the conversion of benzyl halides into benzyl azides and cyanides in good yields. The catalyst could be used at least for five consecutive cycles without appreciable loss in the catalytic activity.
- Mouradzadegun, Arash,Ganjali, Mohammad Reza,Mostafavi, Mahsa Alsadat
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