- Highly Efficient Binuclear Copper-catalyzed Oxidation of N,N-Dimethylanilines with O2
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A binuclear copper-salicylate complex, [Cu(Sal)2(NCMe)]2 (Sal=salicylate), was found to be an active catalyst for the oxidation of N,N-dimethylanilines by O2, affording the corresponding N-methyl-N-phenylformamides as major products. The reactions were carried out with a O2 balloon and the S/C (substrate/catalyst ratio) of the model reaction could be up to 1×105, providing a practical and highly efficient catalytic protocol for accessing N-methyl-N-phenylformamides.
- Liu, Yuxia,Yan, Yonggang,Xue, Dong,Wang, Zhongfu,Xiao, Jianliang,Wang, Chao
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p. 2221 - 2225
(2020/03/23)
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- Catalyst-Free Electrosynthesis of Benzimidazolones through Intramolecular Oxidative C?N Coupling
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The electrochemical synthesis of N, N’-disubstituted benzimidazolones from ureas through an intramolecular anodic dehydrogenative N?H/C?H coupling has been developed. The reaction undergoes under the undivided electrolysis conditions and obviates the need for any catalysts and chemical oxidants. (Figure presented.).
- Li, Jiang-Sheng,Yang, Pan-Pan,Xie, Xin-Yun,Jiang, Si,Tao, Li,Li, Zhi-Wei,Lu, Cui-Hong,Liu, Wei-Dong
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supporting information
p. 1977 - 1981
(2020/04/20)
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- USE OF BENZOTHIAZOLE AMPHIPHILES FOR TREATING TRAUMATIC BRAIN INJURY
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The present invention is directed to methods of reducing symptoms of traumatic brain injury in patients by administering a therapeutically effective amount of a benzothiazole amphiphile compound to a patient suffering from a traumatic brain injury within 0 to 72 hours of incurring the injury.
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Paragraph 0155; 0157
(2019/01/16)
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- Engineering of Nucleic Acids and Synthetic Cofactors as Holo Sensors for Probing Signaling Molecules in the Cellular Membrane Microenvironment
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The comprehensive understanding of the mechanisms underlying the interaction of cells with their membrane microenvironment is of great value for fundamental biological research; however, tracking biomolecules on cell surfaces with high temporal and spatial resolution remains a challenge. Herein, a modular strategy is presented for the construction of cell surface DNA-based sensors by engineering DNA motifs and synthetic cofactors. In this strategy, a stimuli-reactive organic molecule is employed as the cofactor for the DNA motif, and the self-assembly of them forms a FRET-based holo DNA-based sensor. With the use of the DNA-based sensors, the versatility of this modular strategy has been demonstrated in the ratiometric imaging of the cellular extrusion process of endogenous signaling molecules, including sulfur dioxide derivatives and nitric oxide.
- Feng, Guangfu,Luo, Xingyu,Lu, Xu,Xie, Shiyi,Deng, Lu,Kang, Wenyuan,He, Fang,Zhang, Jiaheng,Lei, Chunyang,Lin, Bin,Huang, Yan,Nie, Zhou,Yao, Shouzhuo
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supporting information
p. 6590 - 6594
(2019/05/14)
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- Dichlorophenylacrylonitriles as AhR Ligands That Display Selective Breast Cancer Cytotoxicity in vitro
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Knoevenagel condensation of 3,4-dichloro- and 2,6-dichlorophenylacetonitriles gave a library of dichlorophenylacrylonitriles. Our leads (Z)-2-(3,4-dichlorophenyl)-3-(1H-pyrrol-2-yl)acrylonitrile (5) and (Z)-2-(3,4-dichlorophenyl)-3-(4-nitrophenyl)acryloni
- Baker, Jennifer R.,Gilbert, Jayne,Paula, Stefan,Zhu, Xiao,Sakoff, Jennette A.,McCluskey, Adam
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p. 1447 - 1458
(2018/07/29)
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- BENZOTHIAZOLE AMPHIPHILES
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Disclosed herein, inter alia, are compounds and methods for increasing spine density in a neuron, and for treatment of neuronal diseases and cancer.
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Paragraph 0235
(2017/08/01)
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- Chemoselective Deprotection of Sulfonamides under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications
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Chemoselective acidic hydrolysis of sulfonamides with trifluoromethanesulfonic acid has been evaluated as a deprotection method and further extended to more complex synthetic applications. In contrast to conventional troublesome sulfonamide hydrolysis, a near-stoichiometric amount of acid was found to be sufficient to bring about efficient deprotection of various neutral or electron-deficient N-arylsulfonamides, whereas electron-rich substrates provided sulfonyl group migration products. The deprotection method developed is fully selective for N-arylsulfonamides, and the possibility to discriminate among various different sulfonamides is demonstrated.
- Javorskis, Tomas,Orentas, Edvinas
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p. 13423 - 13439
(2017/12/26)
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- Acetic Acid Accelerated Visible-Light Photoredox Catalyzed N-Demethylation of N,N-Dimethylaminophenyl Derivatives
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N,N-Dimethylaminophenyl moiety is a common fragment in medicinal chemistry as several pharmaceuticals bearing this privileged motif are on the market and under clinical evaluation. Oxidative N-demethylation is generally regarded as the major metabolic pathway. However, pharmacokinetics, metabolites studies as well as the further structural modification are precluded by the impracticality of chemical synthesis. Here we report that acetic acid can significantly accelerate visible-light photoredox catalyzed N-demethylation of N,N-dimethylaminophenyl derivatives. This approach is easy for large scale reaction and even for potential industrial manufacture. (Figure presented.).
- Wu, Guolin,Li, Yazhen,Yu, Xuemei,Gao, Yu,Chen, Haijun
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supporting information
p. 687 - 692
(2017/02/23)
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- Benzothiazole amphiphiles promote the formation of dendritic spines in primary hippocampal neurons
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The majority of excitatory synapses in the brain exist on dendritic spines. Accordingly, the regulation of dendritic spine density in the hippocampus is thought to play a central role in learning and memory. The development of novel methods to control spine density could, therefore, have important implications for treatment of a host of neurodegenerative and developmental cognitive disorders. Herein, we report the design and evaluation of a new class of benzothiazole amphiphiles that exhibit a dosedependent response leading to an increase in dendritic spine density in primary hippocampal neurons. Cell exposure studies reveal that the increase in spine density can persist for days in the presence of these compounds, but returns to normal spine density levels within 24 h when the compounds are removed, demonstrating the capability to reversibly control spinogenic activity. Time-lapse imaging of dissociated hippocampal neuronal cultures shows that these compounds promote a net increase in spine density through the formation of new spines. Biochemical studies support that promotion of spine formation by these compounds is accompanied by Ras activation. These spinogenic molecules were also capable of inhibiting a suspected mechanism for dendritic spine loss induced by Alzheimer-related aggregated amyloid-? peptides in primary neurons. Evaluation of this new group of spinogenic agents reveals that they also exhibit relatively low toxicity at concentrations displaying activity. Collectively, these results suggest that small molecules that promote spine formation could be potentially useful for ameliorating cognitive deficiencies associated with spine loss in neurodegenerative diseases such as Alzheimer disease, and may also find use as general cognitive enhancers.
- Cifelli, Jessica L.,Dozier, Lara,Chung, Tim S.,Patrick, Gentry N.,Yang, Jerry
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p. 11981 - 11992
(2016/07/06)
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- Mn(ii) acetate: An efficient and versatile oxidation catalyst for alcohols
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A homogeneous catalytic system consisting of Mn(ii) acetate (18 μmol), tert-butylhydroperoxide (2.5 mmol), acetonitrile (1.5 mL) and trifluoroacetic acid (91 μmol) was developed for efficient and selective oxidation of various alcohols (1 mmol). The system yielded good to quantitative conversions (42-100%) of various secondary alcohols, such as 2-octanol, fenchyl alcohol and borneol, to their corresponding ketones. Primary alcohols, for example 1-octanol and differently substituted benzyl alcohols, were mainly converted to their corresponding carboxylic acids. Studies with a selection of hydrocarbons, tertiary amines and a cyclic ether isochroman showed that besides alcohols, other substrates can be oxidised as well.
- Raeisaenen, Minna T.,Al-Hunaiti, Afnan,Atosuo, Elisa,Kemell, Marianna,Leskelae, Markku,Repo, Timo
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p. 2564 - 2573
(2014/07/22)
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- Synthesis of three fluorescent boronic acid sensors for tumor marker Sialyl Lewis X in cancer diagnosis
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Sialyl Lewis X (sLex) is a carbohydrate that is considered not only a marker for cancer, but also an antigen associated with the malignant behavior of cancerous cells. We have synthesized three fluorescent boronic acid sensors as potential sensors for sLex. Photoinduced electron transfer by a fluorescence analyzer was used to assess sensor-sLex antigen binding. The reaction was carried out in mixed aqueous solution, and Sensor 3 was identified as showing the strongest fluorescence enhancement upon binding to sLex at 10 nM. In cell-line culture experiments, Sensor 1 was shown to label sLex expression positively for HepG2, Colo 205, and COS-7 cells, and negatively for MDA-MB-231 cells; Sensor 2 did so positively for HepG2, PLC/PRF/5, and Colo 205 cells, and negatively for MDA-MB-231 and COS7 cells; and Sensor 3 did so positively for PLC/PRF/5 and HepG2 cells, and negatively for MDA-MD-231 and COS7 cells. MTT cytotoxicity experiment results showed that the three sensors are nontoxic, and Hoechst 33258 experiments showed that no apoptosis occurred.
- Chang, May-Hua,Chang, Chia-Ni
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supporting information
p. 4437 - 4441
(2014/08/05)
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- Gold catalysis coupled with visible light stimulation: Syntheses of functionalized indoles
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A judicious combination of Au-catalysis and synergistic visible-light stimulation formulates an exceptionally simple and mild reaction system capable of directly coupling anilines and alkynes to form multifunctionalized indoles.
- Cai, Shunyou,Yang, Kai,Wang, David Zhigang
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supporting information
p. 2606 - 2609
(2014/06/09)
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- Discovery of indanone derivatives as multi-target-directed ligands against Alzheimer's disease
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A series of indanone derivatives were designed, synthesized, and tested using a variety of assays to assess their potential as anti-Alzheimer's disease (AD) agents. The investigations assessed the activities of the agents for the inhibition of cholinesterases (AChE and BuChE), the inhibition of amyloid beta (Aβ) self-assembly, and the catalysis of the disassembly of preformed Aβ oligomers and measured their antioxidant activities. Our results demonstrate that most of the synthesized compounds demonstrated good inhibitory activity against AChE with IC50 values in the nanomolar range. In particular, compounds 9 (IC50 Combining double low line 14.8 nM) and 14 (IC50 Combining double low line 18.6 nM) exhibited markedly higher inhibitory activities than tacrine and similar activities to donepezil. In addition, 9 and 14 significantly inhibited Aβ aggregation (inhibition rates of 85.5% and 83.8%, respectively), catalysed the disaggregation of Aβ fibrils generated by self-induced Aβ aggregation, and exhibited antioxidant activity. Furthermore, these two compounds can cross the blood-brain barrier (BBB) in vitro. These properties highlight the potential of these new compounds to be developed as multi-functional drugs for the treatment of Alzheimer's disease.
- Huang, Ling,Miao, Hui,Sun, Yang,Meng, Fanchao,Li, Xingshu
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p. 429 - 439
(2015/01/08)
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- Electrophilic fluorination of N,N-dimethylaniline, N,N-dimethylnaphthalen- 1-amine and 1,8-bis(dimethylamino)naphthalene with N-F reagents
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Reaction of N,N-dimethylaniline, N,N-dimethylnaphthalen-1-amine and 1,8-bis(dimethylamino)- naphthalene (proton sponge) with 1-chloromethyl-4- fluorodiazonia-bicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) and N-fluorobenzenesulfonimide (NFSI) h
- Sorokin, Vladimir I.,Pozharskii, Alexander F.,Ozeryanskii, Valery A.
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- Reductive carbonylation of aryl halides employing a two-chamber reactor: A protocol for the synthesis of aryl aldehydes including 13C- and D-isotope labeling
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A protocol has been developed for conducting the palladium-catalyzed reductive carbonylation of aryl iodides and bromides using 9-methylfluorene-9- carbonyl chloride (COgen) as a source of externally delivered carbon monoxide in a sealed two-chamber system (COware), and potassium formate as the in situ hydride source. The method is tolerant to a wide number of functional groups positioned on the aromatic ring, and it can be exploited for the isotope labeling of the aldehyde group. Hence, reductive carbonylations run with 13COgen provide a facile access to 13C-labeled aromatic aldehydes, whereas with DCO2K, the aldehyde is specifically labeled with deuterium. Two examples of double isotopic labeling are also demonstrated. Finally, the method was applied to the specific carbon-13 labeling of the β-amyloid binding compound, florbetaben.
- Korsager, Signe,Taaning, Rolf H.,Lindhardt, Anders T.,Skrydstrup, Troels
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p. 6112 - 6120
(2013/07/26)
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- A facile and practical copper powder-catalyzed, organic solvent-and ligand-free ullmann amination of aryl halides
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A facile and practical method that the copper powder-catalyzed Ullmann amination of aryl halides with aqueous methylamine under organic solvent-and ligand-free condition at 100 °C and in air gave N-arylamines as sole products in good to excellent yields. The presence of a small amount of air is essential. Other aliphatic primary amines show good to very high reactivity. Secondary amines and aniline are not reactive. Sensitive substituents (i.e., CHO, MeCO, CN and Cl) are tolerable in the reaction.
- Jiao, Jiao,Zhang, Xi-Ru,Chang, Ning-Hui,Wang, Jie,Wei, Jun-Fa,Shi, Xian-Ying,Chen, Zhan-Guo
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supporting information; experimental part
p. 1180 - 1183
(2011/04/24)
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- Design and synthesis of the first generation of dithiolane thiazolidinedione- and phenylacetic acid-based PPARγ agonists
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A series of novel derivatives of potent antioxidant vitamin, α-lipoic acid, and related analogues were designed, synthesized, and evaluated for their PPARγ agonist activities. Compounds 9a and the water soluble analogue 11e were found to be potent PPARγ agonists. Compound 9a appeared to have a significant role in improving insulin sensitivity and reducing triglyceride levels in fa/fa rats as well as inhibited proliferation of a variety of normal and neoplastic cultured human cell types. These novel compounds may prove efficacious not only in the treatment of Type 2 diabetes, but also atherosclerosis, prevention of vascular restenosis, and inflammatory skin diseases.
- Chittiboyina, Amar G.,Venkatraman, Meenakshi S.,Mizuno, Cassia S.,Desai, Prashant V.,Patny, Akshay,Benson, Stephen C.,Ho, Christopher I.,Kurtz, Theodore W.,Pershadsingh, Harrihar A.,Avery, Mitchell A.
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p. 4072 - 4084
(2007/10/03)
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- A reversible reaction inside a self-assembled capsule
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Reversible encapsulation allows the direct observation of the isolated molecules under ambient conditions, at equilibrium and in the liquid phase. Here we show that capsules can amplify and stabilize molecules that are present in only trace concentrations
- Iwasawa, Tetsuo,Mann, Enrique,Rebek Jr., Julius
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p. 9308 - 9309
(2007/10/03)
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- A Convenient Synthesis of Amines from Phenols
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A simple and convenient method for the conversion of substituted phenols into alkylated amines is described; the reaction proceeds via amide formation and subsequent rearrangement of the amide in the presence of alkali.
- Goswami,Goswami,Borthakur,Rastogi
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p. 424 - 425
(2007/10/03)
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- REACTIONS OF N-(4-METHOXYBENZYLIDENE)-N,N-DIALKYLIMINIUM AND 2-(4-METHOXYPHENYL)PYRIDINIUM SALTS WITH ALIPHATIC AMINES
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The reaction of 4-methoxybenzylideneiminium salts with methylamine and dimethylamine on heating results in replacement of the MeO group by an alkylamino-group, whereas the reaction with piperidine affords 3,5-bis-(4-methoxybenzyl)pyridine.N-Methyl-2-(4-me
- Blokhin, A. V.,Tyurekhodzhaeva, M. A.,Bazhenov, D. V.,Bobrovskii, S. I.,Bundel', Yu. G.
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p. 1022 - 1025
(2007/10/02)
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- ACTIVATING EFFECT OF THE IMINIUM GROUP IN AROMATIC NUCLEOPHILIC SUBSTITUTION OF AN ALKOXY GROUP AND HALOGEN ATOMS BY THE ACTION OF NITROGEN BASES
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The characteristics of aromatic nucleophilic substitution with activation by the iminium group in the iminium derivatives of p-alkoxy- and p-halogenobenzaldehydes were investigated.They are determined by the concurrent addition of the nucleophilic agents at the C=N multiple bond.The activating effect of the iminium group depends on the nature of the leaving group, the solvent, the substituent in the benzene ring, and the nature and concentration of the protonating agent.The action of heat on p-methoxybenzylidenemethylamine with a tenfold excess of methylamine hydrochloride in a 30percent alcohol solution of methylamine at 150 deg C for 40 h leads to substitutioon of the methoxymethylamino group with a yield of 90percent.
- Blokhin, A.V.,Bundel, Yu. G.,Terenin, V.I.,Kurtz, A.L.
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p. 2116 - 2123
(2007/10/02)
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- ACTIVATING ACTION OF THE IMMONIUM GROUP IN THE SUBSTITUTION OF ALKOXYL AND HALOGEN ATOMS BY THE ALKYLAMINO GROUP IN THE BENZENE RING
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The substitution of the alkoxy group in o-, p-, and m-alkoxybenzylidenedimethylimmonium iodides by the action of aliphatic amines was investigated.Only p-alkoxy derivatives enter into the reaction forming, after hydrolysis, p-alkyl- and p-dialkylaminobenzaldehydes.Substitution can also be realized in p-alkoxybenzaldehydes and Schiff bases in the presence of the amine hydrochloride.Similarly, the halogen atom in p-halogenobenzaldehydes is substituted by the aliphatic amine residue.Quantum-mechanical calculations of the energy of anionic localization and charge at the attacked carbon atom o f the benzene ring are consistent with the experimantal data.
- Yudin, L. G.,Blokhin, A. V.,Bundel', Yu. G.,Simkin, B. Ya.,Terenin, V. I.
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p. 2064 - 2068
(2007/10/02)
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- Oxazolines
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Compounds of the formula STR1 wherein R1 and R2, independently, are hydrogen, halogen or lower alkyl; R3, R4, R5, R6 and R7, independently, are hydrogen or C1-3 alkyl;
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