- Conversion of alkynes into 1,2-diketones using HFIP as sacrificial hydrogen donor and DMSO as dihydroxylating agent
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A metal-free and hypervalent iodine free conversion of internal alkynes into 1,2-diketo compounds has been described. The efficacy of the present protocol rely on the use of HFIP (1,1,1,3,3,3-Hexafluoro-2-propanol) as reducing agent of alkynes and DMSO as dihydroxylating agent of olefins to acquire the desired chemical transformations. The obtained 1,2-diketones were further transformed into useful derivatives.
- Gujjarappa, Raghuram,Vodnala, Nagaraju,Putta,Ganga Reddy, Velma,Malakar, Chandi C.
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supporting information
(2020/01/21)
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- Design, synthesis and evaluation of 2-amino-imidazol-4-one derivatives as potent β-site amyloid precursor protein cleaving enzyme 1 (BACE-1) inhibitors
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Inhibition of β-site amyloid precursor protein cleaving enzyme 1 (BACE1) to prevent brain β-amyloid (Aβ) peptide's formation is a potential effective approach to treat Alzheimer's disease. In this report we described a structure-based optimization of a series of BACE1 inhibitors derived from an iminopyrimidinone scaffold W-41 (IC50 = 7.1 μM) by Wyeth, which had good selectivity and brain permeability but low activity. The results showed that occupying the S3 cavity of BACE1 enzyme could be an effective strategy to increase the biological activity, and five compounds exhibited stronger inhibitory activity and higher liposolubility than W-41, with L-5 was the most potent inhibitor against BACE1 (IC50 = 0.12 μM, logP = 2.49).
- Fan, Tian-Yuan,Wu, Wen-Yu,Yu, Shao-Peng,Zhong, Yue,Zhao, Chao,Chen, Min,Li, He-Min,Li, Nian-Guang,Chen, Zhi,Chen, Sai,Sun, Zhi-Hui,Duan, Jin-Ao,Shi, Zhi-Hao
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- Tailoring the Molecular Properties with Isomerism Effect of AIEgens
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It is challenging to achieve precise control on the properties of organic π-functional materials to widen their practical applications. On the other hand, the study of aggregation-induced emission luminogens (AIEgens) helps achieve such goals because of i
- Chen, Ming,Liu, Junkai,Liu, Feng,Nie, Han,Zeng, Jiajie,Lin, Gengwei,Qin, Anjun,Tu, Mei,He, Zikai,Sung, Herman H. Y.,Williams, Ian D.,Lam, Jacky W. Y.,Tang, Ben Zhong
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- Preparing method of photocatalytic alpha-diketone compound
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The invention belongs to the technical field of medical and chemical intermediates and related chemicals, and provides a preparing method of photocatalytic alpha-diketone compound. Phenylacetylene and the derivative thereof are used as raw materials, and under the lighting condition, under the combined action of a semiconductor photocatalyst and an additive, alpha-diketone compound is generated through air oxygen in organic solvent. The preparing method has the advantages of being easy to operate, mild in condition and environmentally friendly, has probability of industrialization and obtains the alpha-diketone compound at the high yield, and the catalyst is recyclable. The alpha-diketone compound synthesized through the method can be further functionalized to obtain various compounds applied to development and research of natural products, function materials and fine chemicals.
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Paragraph 0035-0037; 0039-0041
(2017/08/28)
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- Polymer precursor and its manufacturing method for production of nano-ribbon graphene
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An oligophenylene monomer of general formula (I) wherein R1 and R2 are independently of each other H, halogene, —OH, —NH2, —CN, —NO2 or a linear or branched, saturated or unsaturated C1-C40 hydrocarbon residue, which can be substituted 1- to 5-fold with h
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Paragraph 0054; 0082-0084
(2017/01/02)
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- Copper-catalyzed base-accelerated direct oxidation of C-H bond to synthesize benzils, isatins, and quinoxalines with molecular oxygen as terminal oxidant
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We describe herein an efficient and general copper (II)-catalyzed base-accelerated oxidation of the C-H bond to synthesize benzils and isatins. With similar oxidation system an efficient one-pot procedure for the synthesis of quinoxaline derivatives was realized. The two protocols feature using molecular oxygen as terminal oxidant, low catalyst loading, wide substrate scope, and high functional-group tolerance.
- Yu, Jing-Wen,Mao, Shuai,Wang, Yong-Qiang
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p. 1575 - 1580
(2015/03/14)
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- Asymmetric transfer hydrogenation of unsymmetrical benzils
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In this paper, the asymmetric transfer hydrogenation of unsymmetrical benzils with m, p-substituents was conducted with a substrate/catalyst molar ratio of 100 at 40°C for 24 h to produce (S,S)-hydrobenzoins in good yields (76.2% to 97.1%) with high diastereomeric (syn/anti = 10.8 to 29.7/1) and enantiomeric purities (86.1%ee syn to 98.9%ee syn). Unfortunately, the unsymmetrical benzils with the o-substituents such as electron-donating (R = CH3, OCH3) and electron-withdrawing groups (R = F, Cl, CF3) resulted in poor yields (0% to 31.2%), even at 40°C for 72 h. These products had inefficient diastereoselectivities (syn/anti = 1.5 to 5.0/1) caused by steric effects. Furthermore, the results of a dynamic-kinetic study were used to propose a plausible reaction pathway of unsymmetrical benzil using 3-methoxy-1,2-diphenyl ethanedione as an example.
- Zhang, Hao,Feng, Dandan,Sheng, Haibo,Ma, Xuebing,Wan, Jinwei,Tang, Qian
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p. 6417 - 6423
(2014/02/14)
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- One-pot, two-step desymmetrization of symmetrical benzils catalyzed by the methylsulfinyl (dimsyl) anion
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An operationally simple one-pot, two-step procedure for the desymmetrization of benzils is herein described. This consists in the chemoselective cross-benzoin reaction of symmetrical benzils with aromatic aldehydes catalyzed by the methyl sulfinyl (dimsyl) anion, followed by microwave-assisted oxidation of the resulting benzoylated benzoins with nitrate, avoiding the costly isolation procedure. Both electron-withdrawing and electron-donating substituents may be accommodated on the aromatic rings of the final unsymmetrical benzil. the Partner Organisations 2014.
- Ragno, Daniele,Bortolini, Olga,Giovannini, Pier Paolo,Massi, Alessandro,Pacifico, Salvatore,Zaghi, Anna
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p. 5733 - 5744
(2014/07/22)
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- POLYMERIC PRECURSORS FOR PRODUCING GRAPHENE NANORIBBONS AND METHODS FOR PREPARING THEM
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An oligophenylene monomer of general formula (I) wherein R1 and R2 are independently of each other H, halogene, —OH, —NH2, —CN, —NO2 or a linear or branched, saturated or unsaturated C1-C40 /sub
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Page/Page column
(2014/12/09)
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- Catalyst-controlled highly selective coupling and oxygenation of olefins: A direct approach to alcohols, ketones, and diketones
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Oxygen? That's radical! A method for the direct synthesis of substituted alcohols, ketones, and diketones through a catalyst-controlled highly chemoselective coupling and oxygenation of olefins has been developed. The method is simple and practical, can be switched by the selection of different catalysts, and employs molecular oxygen as both an oxidant and a reagent. Copyright
- Su, Yijin,Sun, Xiang,Wu, Guolin,Jiao, Ning
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supporting information
p. 9808 - 9812
(2013/09/23)
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- Facile and highly chemoselective synthesis of benzil derivatives via oxidation of stilbenes in an I2-H2O system
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A facile and highly chemoselective protocol for the synthesis of benzil derivatives has been developed by oxidation of stilbenes in an I 2-H2O system under air. Notably, the method was applicable to 26 examples and provided up to 98% yield, avoiding the use of acid, metal catalysts and so on.
- Zeng, Xianghua,Miao, Chengxia,Wang, Shoufeng,Xia, Chungu,Sun, Wei
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p. 9666 - 9669
(2013/09/02)
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- Discovery of an orally available, brain penetrant BACE1 inhibitor that affords robust CNS Aβ reduction
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Inhibition of BACE1 to prevent brain Aβ peptide formation is a potential disease-modifying approach to the treatment of Alzheimer's disease. Despite over a decade of drug discovery efforts, the identification of brain-penetrant BACE1 inhibitors that substantially lower CNS Aβ levels following systemic administration remains challenging. In this report we describe structure-based optimization of a series of brain-penetrant BACE1 inhibitors derived from an iminopyrimidinone scaffold. Application of structure-based design in tandem with control of physicochemical properties culminated in the discovery of compound 16, which potently reduced cortex and CSF Aβ40 levels when administered orally to rats.
- Stamford, Andrew W.,Scott, Jack D.,Li, Sarah W.,Babu, Suresh,Tadesse, Dawit,Hunter, Rachael,Wu, Yusheng,Misiaszek, Jeffrey,Cumming, Jared N.,Gilbert, Eric J.,Huang, Chunli,McKittrick, Brian A.,Hong, Liwu,Guo, Tao,Zhu, Zhaoning,Strickland, Corey,Orth, Peter,Voigt, Johannes H.,Kennedy, Matthew E.,Chen, Xia,Kuvelkar, Reshma,Hodgson, Robert,Hyde, Lynn A.,Cox, Kathleen,Favreau, Leonard,Parker, Eric M.,Greenlee, William J.
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supporting information
p. 897 - 902
(2013/01/15)
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- Structure based design of iminohydantoin BACE1 inhibitors: Identification of an orally available, centrally active BACE1 inhibitor
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From an initial lead 1, a structure-based design approach led to identification of a novel, high-affinity iminohydantoin BACE1 inhibitor that lowers CNS-derived Aβ following oral administration to rats. Herein we report SAR development in the S3 and F′ subsites of BACE1 for this series, the synthetic approaches employed in this effort, and in vivo data for the optimized compound.
- Cumming, Jared N.,Smith, Elizabeth M.,Wang, Lingyan,Misiaszek, Jeffrey,Durkin, James,Pan, Jianping,Iserloh, Ulrich,Wu, Yusheng,Zhu, Zhaoning,Strickland, Corey,Voigt, Johannes,Chen, Xia,Kennedy, Matthew E.,Kuvelkar, Reshma,Hyde, Lynn A.,Cox, Kathleen,Favreau, Leonard,Czarniecki, Michael F.,Greenlee, William J.,McKittrick, Brian A.,Parker, Eric M.,Stamford, Andrew W.
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scheme or table
p. 2444 - 2449
(2012/05/19)
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- Iron-promoted C - C bond cleavage of 1,3-diketones: A route to 1,2-diketones under mild reaction conditions
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A conceptual method for the preparation of 1,2-diketones is reported. The selective C - C bond cleavage of 1,3-diketones affords the 1,2-diketones in high yields under mild reaction conditions in air by the use of FeCl3 as the catalyst and tert-butyl nitrite (TBN) as the oxidant without the use of solvent. The possible reaction mechanism is discussed. This protocol provides an expeditious route to the useful 1,2-diketones.
- Huang, Lehao,Cheng, Kai,Yao, Bangben,Xie, Yongju,Zhang, Yuhong
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experimental part
p. 5732 - 5737
(2011/08/22)
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- NOVEL 2-AMINO-IMIDAZOLE-4-ONE COMPOUNDS AND THEIR USE IN THE MANUFACTURE OF A MEDICAMENT TO BE USED IN THE TREATMENT OF COGNITIVE IMPAIRMENT, ALZHEIMER’S DISEASE, NEURODEGENERATION AND DEMENTIA
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This invention relates to novel compounds having the structural formula I below and to their pharmaceutically acceptable salts, compositions and methods of use. These novel compounds provide a treatment or prophylaxis of cognitive impairment, Alzheimer Di
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Page/Page column 86-87
(2008/06/13)
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- 2, 3, and 4 (α,α,β,β Tetrafluorophenethyl)benzylamines. A new class of antiarrhythmic agents
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Upon finding 2-(α,α,β,β-tetrafluorophenethyl)benzylamine (4) to be a potent and novel type of antiarrhythmic agent, 2-, 3-, and 4-(α,α,β,β-Tetrafluorophenethyl) benzylamines were synthesized. Structure-activity relationships in this series are described.
- Christy,Colton,Mackay,Staas,Wong,Engelhardt,Torchiana,Stone
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p. 421 - 430
(2007/10/06)
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- Tetrafluorophenethylaralkylamine compounds
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New fluoro derivatives of aralkylamine compounds, particularly 2-(2-phenyl-1,1,2,2-tetrafluoroethyl)benzylamine, as well as the N-alkyl and the N,N-dialkyl derivatives thereof are prepared by reaction of 2-bromobenzonitrile with benzylmagnesium chloride to produce 2'-bromo-2-phenylacetophenone; oxidation of said acetophenone with selenous acid to produce 2-bromobenzil; conversion of the benzil compound by treatment with sulfur tetrafluoride to the corresponding 2-bromo-α ,α-α',α'-tetrafluorobibenzyl; followed by reaction of the 2-bromobibenzyl compound with a metal cyanide to produce the corresponding 2-(2-phenyl-1,1,2,2-tetrafluoroethyl)benzonitrile. This nitrile compound is then reduced with lithium aluminum hydride to produce the corresponding benzylamine, which is then converted, if desired, to the N-alkyl and/or N,N-dialkyl 2-(2-phenyl-1,1,2,2-tetrafluoroethyl)benzylamine. Alternatively, the nitrile or the precursor bromobibenzyl can be converted by Grignard reactions to the corresponding α-alkyl or α,α-dialkylbenzylamine which can then be converted if desired to the corresponding N-alkyl and/or N,N-dialkyl substituted benzylamine compound. The phenyltetrafluoroethylbenzylamine as well as its N-alkyl and N,N-dialkyl derivatives are active as antiarrhythmic agents.
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