- Discovery of Novel Acetamide-Based Heme Oxygenase-1 Inhibitors with PotentIn VitroAntiproliferative Activity
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Heme oxygenase-1 (HO-1) promotes heme catabolism exercising cytoprotective roles in normal and cancer cells. Herein, we report the design, synthesis, molecular modeling, and biological evaluation of novel HO-1 inhibitors. Specifically, an amide linker in the central spacer and an imidazole were fixed, and the hydrophobic moiety required by the pharmacophore was largely modified. In many tumors, overexpression of HO-1 correlates with poor prognosis and chemoresistance, suggesting the inhibition of HO-1 as a possible antitumor strategy. Accordingly, compounds7iand7l-pemerged for their potency against HO-1 and were investigated for their anticancer activity against prostate (DU145), lung (A549), and glioblastoma (U87MG, A172) cancer cells. The selected compounds showed the best activity toward U87MG cells. Compound7lwas further investigated for its in-cell enzymatic HO-1 activity, expression levels, and effects on cell invasion and vascular endothelial growth factor (VEGF) extracellular release. The obtained data suggest that7lcan reduce cell invasivity acting through modulation of HO-1 expression.
- Fallica, Antonino N.,Sorrenti, Valeria,D’Amico, Agata G.,Salerno, Loredana,Romeo, Giuseppe,Intagliata, Sebastiano,Consoli, Valeria,Floresta, Giuseppe,Rescifina, Antonio,D’Agata, Velia,Vanella, Luca,Pittalà, Valeria
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p. 13373 - 13393
(2021/09/20)
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- Novel palladium nanoparticles supported on β-cyclodextrin@graphene oxide as magnetically recyclable catalyst for Suzuki–Miyaura cross-coupling reaction with two different approaches in bio-based solvents
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A novel nanocatalyst was designed and prepared. Initially, the surface of magnetic graphene oxide (M-GO) was modified using thionyl chloride, tris(hydroxymethyl)aminomethane and acryloyl chloride as linkers which provide reactive C═C bonds for the polymerization of vinylic monomers. Separately, β-cyclodextrin (β-CD) was treated with acryloyl chloride to provide a modified β-CD. Then, in the presence methylenebisacrylamide as a cross-linker, monomers of modified β-CD and acrylamide were polymerized on the surface of the pre-prepared M-GO. Finally, palladium acetate and sodium borohydride were added to this composite to afford supported palladium nanoparticles. This fabricated nanocomposite was fully characterized using various techniques. The efficiency of this easily separable and reusable heterogeneous catalyst was successfully examined in Suzuki–Miyaura cross-coupling reactions of aryl halides and boronic acid as well as in modified Suzuki–Miyaura cross-coupling reactions of N-acylsuccinimides and boronic acid in green media. The results showed that the nanocatalyst was efficient in coupling reactions for direct formation of the corresponding biphenyl as well as benzophenone derivatives in green media based on bio-based solvents. In addition, the nanocatalyst was easily separable, using an external magnet, and could be reused several times without significant loss of activity under the optimum reaction conditions.
- Heidari, Bahareh,Heravi, Majid M.,Nabid, Mohammad Reza,Sedghi, Roya,Hooshmand, Seyyed Emad
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- Polymer-incarcerated palladium-catalyzed facile: In situ carbonylation for the synthesis of aryl aldehydes and diaryl ketones using CO surrogates under ambient conditions
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In this existing work, an efficient polymer-supported palladium catalyst, a furfurylamine-functionalized Merrifield complex of palladium [Pd@(Merf-FA)], was synthesized and characterized, showing excellent catalytic activity towards in situ carbonylation reactions using carbon monoxide surrogates like formic acid and chloroform. Herein, we examined the catalytic activity of the Pd@(Merf-FA) catalyst for the formylation of aryl iodides and carbonylative Suzuki-Miyaura coupling reactions. The Pd@(Merf-FA) catalyst was systematically characterized by several techniques like HRTEM, elemental mapping, PXRD, TGA-DTA, FESEM, UV-vis, EDAX, CHN and AAS analysis. The catalyst is highly recyclable, able to be recycled up to six times without showing any significant decrease in catalytic activity. The [Pd@(Merf-FA)] catalyst proved to be more efficient compared to the corresponding homogeneous palladium catalyst. In addition, the leaching experiment of the synthesized catalyst was studied, which showed that negligible leaching of metal occurred from the polymeric support.
- Dey, Tusar Kanto,Basu, Priyanka,Riyajuddin, Sk,Ghosh, Aniruddha,Ghosh, Kaushik,Manirul Islam, Sk
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p. 9802 - 9814
(2019/07/04)
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- High-efficiency long-service life organic room-temperature phosphorescence material and preparation method thereof
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The invention provides an alkoxy, benzyloxy or bromine substituted xanthone derivative and a preparation method thereof. The xanthone derivative is simple in preparation method, has a phosphorescencepeak on a long wavelength peak and is long in phosphorescence service life and high in light emission efficiency. The preparation method of the xanthone derivative comprises the following preparationsteps: 1, putting phenol, potassium carbonate, DMF (Dimethyl Formamide) and methylbenzene into a reaction container, backflowing for 3-5 hours in a nitrogen environment, and carrying out dehydration treatment till the system has no water generation; removing the methylbenzene, recovering to the room temperature, adding 4-bromine-2-fluorobenzonitrile, backflowing for 3-5 hours in the nitrogen environment, after the reaction is completed, diluting the solution with 100mL of methylbenzene, filtering, washing with water, drying so as to obtain a crude product of a crystal, and purifying with a spectrum column so as to obtain an intermediate as shown in the specification; 2, mixing the intermediate obtained in the step 1 with water and sulfuric acid, heating to 150-200 DEG C in the nitrogen environment, stirring, and backflowing for 10-15 hours; after the reaction is completed, cooling to the room temperature, diluting with water, extracting by using trichloromethane and a saturated sodiumchloride solution, combining organic phases, drying, filtering, carrying out vacuum distillation so as to remove the solvent and obtain a crude product of a crystal, and purifying with a spectrum column, so as to obtain an intermediate as shown in the specification.
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Paragraph 0034; 0035
(2019/01/08)
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- Pd(II)-Catalyzed Denitrogenative and Desulfinative Addition of Arylsulfonyl Hydrazides with Nitriles
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A Pd(II)-catalyzed denitrogenative and desulfinative addition of arylsulfonyl hydrazides with nitriles has been successfully achieved under mild conditions. This transformation is a new method for the addition reaction to nitriles with arylsulfonyl hydrazides as arylating agent, thus providing an alternative synthesis of aryl ketones. The reported addition reaction is tolerant to many common functional groups, and works well in the presence of electron-donating and electron-withdrawing substituents. Notably, the reported denitrogenative and desulfinative addition was also appropriate for alkyl nitriles, making this newly developed transformation attractive.
- Meng, Mengting,Yang, Liangfeng,Cheng, Kai,Qi, Chenze
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p. 3275 - 3284
(2018/03/25)
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- Preparation method of aromatic ketone
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The invention discloses a preparation method of aromatic ketone. Under the effects of a palladium catalyst and a nitrogen-containing ligand, nitrile compounds and arylsulfonylhydrazide take desulfurization addition reaction in an organic solvent; after the reaction is completed, post treatment is performed to obtain aromatic ketone. The reaction is applicable to aromatic nitrile compounds, and isalso applicable to aliphatic nitrile compounds; the reaction realizes the wide substrate applicability and functional group tolerance; the potential application value is realized in the aspect of aryl-carbonyl building.
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Paragraph 0046; 0047; 0048; 0050
(2018/09/11)
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- Palladium-catalyzed synthesis of diaryl ketones from aldehydes and (hetero)aryl halides via C-H bond activation
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We developed a palladium-catalyzed C-H transformation that enabled the synthesis of ketones from aldehydes and (hetero)aryl halides. The use of picolinamide ligands was key to achieving the transformation. Heteroaryl ketones, as well as diaryl ketones, were synthesized in good to excellent yields, even in gram-scale, using this reaction. Results of density functional theory (DFT) calculations support the C-H bond activation pathway.
- Wakaki, Takayuki,Togo, Takaya,Yoshidome, Daisuke,Kuninobu, Yoichiro,Kanai, Motomu
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p. 3123 - 3128
(2018/04/14)
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- Method for preparing aromatic ketone in aqueous phase
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The invention discloses a method for preparing aromatic ketone in an aqueous phase, comprising the following steps: enabling aryl formyl potassium formate and aryl potassium fluoborate to generate decarboxylation acylation reaction in water under the actions of a silver catalyst and an oxidizing agent, and performing treatment after reaction is ended to obtain the disclosed aromatic ketone. According to the preparation method, the silver catalyst replaces a noble metal catalyst, water is taken as a solvent, an aromatic ketone product is obtained with relatively high yield, the adopted catalystis low in cost and easy to obtain, reaction conditions are mild, and meanwhile, the product is good in university, and therefore, the method has good application potential.
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Paragraph 0042-0045
(2018/04/26)
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- Ag(i)/persulfate-catalyzed decarboxylative coupling of α-oxocarboxylates with organotrifluoroborates in water under room temperature
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The decarboxylative coupling reaction of α-oxocarboxylates and organotrifluoroborates was carried out smoothly in the presence of catalytic AgNO3 using K2S2O8 as oxidant to generate diarylketone products in high
- Chang, Sheng,Wang, Jian Feng,Dong, Lin Lin,Wang, Dan,Feng, Bo,Shi, Yuan Tai
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p. 51928 - 51934
(2017/11/22)
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- Carbonylative coupling of aryl tosylates/triflates with arylboronic acids under CO atmosphere
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The carbonylative Suzuki-Miyaura reaction between aryl tosylates/triflates with arylboronic acid is herein reported, using base-free conditions and a balloon pressure of carbon monoxide. Under these conditions, unsymmetrical biaryl ketones were obtained in modest to excellent yields. This method was adapted to the synthesis of oxybenzone and ketoprofen in good yields under mild conditions.
- Hao, Cheng Yi,Wang, Dan,Li, Ya Wei,Dong, Lin Lin,Jin, Ying,Zhang, Xiu Rong,Zhu, He Yun,Chang, Sheng
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p. 86502 - 86509
(2016/09/23)
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- Silver-catalyzed decarboxylative acylation of arylglyoxylic acids with arylboronic acids
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The silver-catalyzed coupling of arylboronic acids with arylglyoxylic acids was found to be an extremely efficient route for the synthesis of unsymmetrical diaryl ketones. It can be conducted on a gram scale under mild and open-flask conditions with good functional group compatibility, avoiding the addition of expensive and/or toxic metals. This journal is
- Cheng, Kai,Zhao, Baoli,Qi, Chenze
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p. 48698 - 48702
(2014/12/10)
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- Palladium-Catalyzed Synthesis of Biaryl Ketones via tert -Butyl Isocyanide Insertion
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A simple and efficient palladium-catalyzed carbonylative Suzuki coupling via tert-butyl isocyanide insertion has been developed, which demonstrates the utility of isocyanides in intermolecular C-C bond construction. This methodology provides a novel pathway for the synthesis of diaryl ketones in moderate to good yields. The approach is tolerant to a wide range of substrates and applicable to library synthesis. A possible reaction mechanism was proposed based on the experimental results. Georg Thieme Verlag Stuttgart. New York.
- Chen, Zhong,Duan, Huaqing,Jiang, Xiao,Wang, Jinmei,Zhu, Yongming,Yang, Shilin
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supporting information
p. 1425 - 1430
(2014/06/23)
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- DMC mediated one pot synthesis of biaryl ketones from aryl carboxylic and boronic acids
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Synthesis of biaryl ketones has been realized from aryl carboxylic acids in the presence of DMC, facilitated by palladium catalyst under thermal condition. This methodology gives the introduction of carbonyl functionality in one pot from corresponding ary
- Pathak, Arunendra,Rajput, Chatrasal S.,Bora, Pushkar S.,Sharma, Somesh
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p. 2149 - 2150
(2013/05/08)
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- CONDENSED COMPOUNDS WITH ACTIVITY AT ESTROGEN RECEPTORS
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Disclosed herein are compounds of Formula (I) as disclosed herein, methods of modulating the activity of an estrogen receptor and methods of treating a disorder associated with estrogen receptors.
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Page/Page column 47-48
(2009/05/30)
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- COMPOUNDS WITH ACTIVITY AT ESTROGEN RECEPTORS
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Disclosed herein are methods of treating neuropathic pain, reducing inflammation, reducing IL-4 levels, and reducing IFN-γ levels, using various di-aromatic compounds for use as estrogen receptors β agonists.
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Page/Page column 68
(2010/11/30)
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- A rapid, solvent-free, ligandless and mild method for preparing aromatic ketones from acyl chlorides and arylboronic acids via a Suzuki-Miyaura type of coupling reaction
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Aromatic ketones were synthesized via a palladium catalyzed cross-coupling reaction of boronic acids with acyl chlorides in the presence of Na 2CO3 at room temperature under solvent-free conditions. The ligand-free and mild reaction conditions, highly rapid reaction rate and good to excellent yields are important features of this method.
- Bandgar,Patil
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p. 7627 - 7630
(2007/10/03)
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- Highly chemoselective hydrogenolysis of iodoarenes
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The catalytic hydrodehalogenation reaction using molecular hydrogen and Pd/C has been revisited. It is shown that the speed of removal of halogen increases with increasing electronegativity I Br Cl. Nevertheless, selective dehydrohalogenation in compounds containing other reducible functions can be achieved only with iodine and not with bromine or chlorine. Selective deiodination of iodobenzophenone could be accomplished without reducing the carbonyl group. Hydrogenolysis of azidoiodoaromatic compounds to the corresponding azido compounds is high yielding. This selectivity was exploited for the labeling of benzophenone- and azido-containing compounds by deuterium and tritium.
- Faucher, Nicolas,Ambroise, Yves,Cintrat, Jean-Christophe,Doris, Eric,Pillon, Florence,Rousseau, Bernard
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p. 932 - 934
(2007/10/03)
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- Heterocyclic spiro compounds
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The invention provides new compounds pertaining to the class of: aryl methoxy phenyl alkyl heterocyclic spiro compounds, enantiomers, diastereoisomers and physiologically-tolerable salts thereof. For example: 8-{2-?3-quinol-2-yl methoxy)phenyl!ethyl}-3,8-diaza-1-oxa-2-oxo spiro?4,5!decane is described. Medicinal products containing the same are useful in the treatment of any pathology involving modifications of leukotriene metabolism.
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