- KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot
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A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is
- Gurawa, Aakanksha,Kumar, Manoj,Rao, Dodla S.,Kashyap, Sudhir
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supporting information
p. 16702 - 16707
(2020/10/27)
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- Static phase transfer catalysis for Williamson reactions: Pickering interfacial catalysis
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Pickering interfacial catalysis (PIC) systems are regarded as an innovative platform for the design of efficient static biphasic catalytic reactions. In this study, a static PIC system with high catalytic activity was constructed for a phase transfer cata
- Zhao, Qianqiang,Zhao, Xiao,Peng, Hui,Liu, Yang,Yang, Lihui,Sun, Jie,Yang, Lei,Shen, Yifeng
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p. 3445 - 3453
(2019/07/10)
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- Discovery of 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-phenylacetamide derivatives as new potent and selective human sirtuin 2 inhibitors
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Human sirtuin 2 (SIRT2) plays pivotal roles in multiple biological processes such as cell cycle regulation, autophagy, immune and inflammatory responses. Dysregulation of SIRT2 was considered as a main aspect contributing to several human diseases, including cancer. Development of new potent and selective SIRT2 inhibitors is currently desirable, which may provide a new strategy for treatment of related diseases. Herein, a structure-based optimization approach led to new 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-phenylacetamide derivatives as SIRT2 inhibitors. SAR analyses with new synthesized derivatives revealed a number of new potent SIRT2 inhibitors, among which 28e is the most potent inhibitor with an IC50 value of 42?nM. The selectivity analyses found that 28e has a very good selectivity to SIRT2 over SIRT1 and SIRT3. In cellular assays, 28e showed a potent ability to inhibit human breast cancer cell line MCF-7 and increase the acetylation of α-tubulin in a dose-dependent manner. This study will aid further efforts to develop highly potent and selective SIRT2 inhibitors for the treatment of cancer and other related diseases.
- Yang, Lingling,Ma, Xiaobo,Yuan, Chen,He, Yanying,Li, Ling,Fang, Sha,Xia, Wei,He, Tao,Qian, Shan,Xu, Zhihong,Li, Guobo,Wang, Zhouyu
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p. 230 - 241
(2017/04/19)
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- N-(4-substituted phenyl)-2-substituted acetamide compound and is use as SIRT2 protein inhibitor
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The invention discloses a compound shown in the formula I or its pharmaceutically acceptable salt, crystalline form and solvate. X represents a group shown in the description, Y represents a group shown in the description, R1, R2 and R3 independently represent H, hydroxyl, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl or phenyl, and R4 represents aryl, heteroaryl, substituted aryl or substituted heteroaryl. The novel compound shown in the formula I has good inhibition activity to SIRT2 and tumors, has a good medicinal value and provides a novel potential choice for clinical medication.
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Paragraph 0160; 0161
(2017/08/02)
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- Tetrabutyl ammonium bromide-mediated benzylation of phenols in water under mild condition
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Benzylation of phenol was successfully achieved in water under room temperature mediated by tetrabutylammonium bromide (TBAB) for only 2 h affording the corresponding benzyl phenyl ether with good to excellent yields. This protocol is very efficient, simple, avoiding catalysts, easy to work-up after reaction, and especially 'green'.
- Wang, Hailei,Ma, Yuping,Tian, Heng,Yu, Ajuan,Chang, Junbiao,Wu, Yangjie
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p. 2669 - 2673
(2014/04/03)
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- Catalytic aerobic synthesis of aromatic ethers from non-aromatic precursors
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Only little waste: Aryl ether formation is accomplished by oxidative condensation of alcohols and 2-cyclohexenones. The reaction complements the existing methods used by synthetic chemists to obtain aryl ethers, and allows a straightforward access to a wide range of functionalized products. In addition, the catalytic reaction with O2 as the oxidant generates water as the only by-product and provides a greener approach to aryl ethers. Copyright
- Simon, Marc-Olivier,Girard, Simon A.,Li, Chao-Jun
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supporting information; experimental part
p. 7537 - 7540
(2012/09/10)
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- A PEG1000-DAIL[CdCl3]-toluene temperature-dependent biphasic system that regulates homogeneously catalyzed C-O coupling of organic halides with phenols and alcohols under ligand-free conditions
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An efficient, experimentally simple, and convenient procedure for the C-O coupling of organic halides with phenols and alcohols in a PEG 1000-DAIL[CdCl3]-toluene temperature-dependent biphasic system has been developed. The product can be easily isolated by a simple decantation, and the catalytic system can be recycled and reused without loss of catalytic activity.
- Hu, Yu Lin,Ma, Xiao Yun,Lu, Ming
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experimental part
p. 471 - 480
(2011/06/22)
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- Di-p-nitrobenzyl azodicarboxylate (DNAD): An alternative azo-reagent for the Mitsunobu reaction
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Di-p-nitrobenzyl azodicarboxylate is prepared in 83.6% yield in two steps as a bright yellow solid, which can be used as an azo-reagent in the Mitsunobu reaction. When a chiral secondary alcohol was used, sufficient configurational inversion of alcohol occurred under Mitsunobu conditions. That the hydrazine produced from DNAD is semisoluble in some solvents such as THF and CH 2Cl2 makes it separated easily from the reaction mixture just via filtration. Then the recovered hydrazine compound can be re-exposed to oxidant to produce DNAD. Because DNAD is more stable than DIAD at ambient temperatures and allows easy separation, it is a good alternative azo-reagent for the Mitsunobu reaction.
- Yang, Jianhai,Dai, Liyan,Wang, Xiaozhong,Chen, Yingqi
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experimental part
p. 1456 - 1462
(2011/03/21)
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- Ionic liquids as reagent and reaction medium: Preparation of alkyl aryl ethers
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Room temperature ionic liquid, [bmIm]OH, is used as a green recyclable reaction medium and reagent for the alkylation of phenols in excellent yields. The recovered ionic liquid was reused five to six times with consistent activity.
- Mohanazadeh, Farajollah,Aghvami, Majid
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- Cesium fluoride-Celite: A solid base for efficient syntheses of aromatic esters and ethers
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Coupling reactions of a number of aromatic and heteroaromatic phenols with alkyl, acyl or benzoyl halides in acetonitrile with cesium fluoride-Celite are described, demonstrating that this reagent provides an efficient, convenient and practical method for the syntheses of aromatic esters and ethers.
- Shah, Syed Tasadaque Ali,Khan, Khalid Mohammed,Hussain, Hidayat,Anwar, Muhammad Usman,Fecker, Miriam,Voelter, Wolfgang
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p. 6652 - 6656
(2007/10/03)
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- SELECTIVE ESTROGEN RECEPTOR MODULATORS
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The present invention provides a compound represented by the following formula (I); [wherein T represents a single bond, a C1-C4 alkylene group which may have a substituent and the like; formula (I-1) represents a single bond or a double bond; A represents a single bond, a bivalent 5- to 14-membered heterocyclic group which may have a substituent and the like; Y represents a single bond and the like; Z represents a methylene group and the like; ring G represents a phenylene group and the like which may condense with a 5- to 6-membered ring and may have a heteroatom; Ra and Rb are the same as or different from each other and represent a hydrogen atom and the like; W represents a single bond and the like; R' represents 1 to 4 independent hydrogen atoms and the like; and R" represents 1 to 4 independent hydrogen atoms and the like] or a salt thereof, or a hydrate thereof.
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Page/Page column 114
(2008/06/13)
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- Copper(II)-catalyzed ether synthesis from aliphatic alcohols and potassium organotrifluoroborate salts
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(Matrix presented) A protocol for the copper(II)-catalyzed etherification of aliphatic alcohols under mild and essentially neutral conditions is described. Air- and moisture-stable potassium alkenyl- and aryltrifluoroborate salts undergo cross-coupling with a variety of aliphatic primary and secondary alcohols and phenols, and are tolerant of a range of functional groups. The optimized conditions utilize catalytic copper(II) acetate with 4-(dimethylamino)pyridine as ligand in the presence of 4 A molecular sieves under an atmosphere of oxygen.
- Quach, Tan D.,Batey, Robert A.
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p. 1381 - 1384
(2007/10/03)
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- An efficient approach towards syntheses of ethers and esters using CsF-Celite as a solid base
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The coupling reactions of a number of alcohols and phenols with alkyl, acyl or benzoyl halides in acetonitrile with cesium fluoride-Celite are described. It has been found that CsF-Celite combinations provide an efficient, convenient and practical method for syntheses of both, ethers and esters.
- Shah, Syed Tasadaque A,Khan, Khalid M,Heinrich, Angelica M,Choudhary, M.Iqbal,Voelter
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p. 8603 - 8606
(2007/10/03)
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- Isotope effects in nucleophilic substitution reactions X. The effect of changing the nucleophilic atom on ion-pairing in an S(N)2 reaction
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The effect of ion-pairing in an S(N)2 reaction is very different when the nucleophilic atom is changed from sulfur to oxygen, i.e., changing the nucleophile from thiophenoxide ion to phenoxide ion. When the nucleophile is sodium thiophenoxide, ion-pairing markedly alters the secondary α-deuterium kinetic isotope effect (transition state structure) and the substituent effect found by changing the para substituent on the nucleophile. When the nucleophile is sodium phenoxide, ion-pairing does not significantly affect the secondary α-deuterium or the chlorine leaving group kinetic isotope effects (transition state structure) or the substituent effects found by changing a para substituent on the nucleophile or the substrate. The different effects of ion-pairing may occur because the electron density on the hard oxygen atom of the sodium phenoxide is not affected significantly by ion-pairing.
- Fang, Yao-Ren,Lai, Zhu-Gen,Westaway, Kenneth Charles
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p. 758 - 764
(2007/10/03)
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- Synthesis of aromatic ethers without organic solvent and inorganic carrier under microwave irradiation
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A simple, rapid and efficient procedure for the synthesis of aromatic ethers via microwave irradiation without any organic solvent and inorganic carrier is reported.
- Wang, Jin-Xian,Zhang, Manli,Xing, Zhiliang,Hu, Yulai
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p. 301 - 305
(2007/10/03)
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- Electron Apportionment in Cleavage of Radical Anions. 1. Nitro-Substituted Benzyl Phenyl Ethers
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The radical anions of 4-nitrobenzyl phenyl ethers undergo cleavage at least 10E4 times faster than the radical anions of corresponding 4-nitrophenyl benzyl ethers despite a perceived thermodynamic advantage for the latter set of reactions.It is suggested that this results reflects a kinetic advantage for cleavage reactions which take place with regioconservation of spin density.
- Maslak, Przemyslaw,Guthrie, Robert D.
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p. 2628 - 2636
(2007/10/02)
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- Substituted N-arylazetidinones, β-lactamases potential inhibitors
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Two classes of substituted N-aryl azetidinones have been prepared by cyclization of various β-bromopropionanilides. The 7a class possess a carboxylic function in ortho, meta or para of the nitrogen and possibly another alkyl substituent on the aromatic nucleus. In the 7a class, the aromatic nucleus is substituted by a bromomethyl group instead of the alkyl one. Few of these azetidinones show a good affinity for various cell-free β-lactamases preparations, and thus are pretty good competitive inhibitors. Nevertheless, they do not act synergistically with ampicillin on β-lactamase producing bacterial strains. A poor antibacterial activity has been detected for few compounds. The azetidinones 7b which possess a latent electrophilic quinonimine methide function, do not give any progressive (suicide type) inhibition, or inactivation, of the enzymatic activity.
- Zrihen,Labia,Wakselman
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p. 307 - 314
(2007/10/02)
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