- Catalytic hydrogenation and reduction of 4-(2,2,2-trifluoroethoxy)nitrobenzene
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4-(2,2,2-Trifluoroethoxy)nitrobenzene was used as raw material to create a reaction for 1 h at 70°C by using ethanol and palladium carbon as solvent and catalyst, respectively, to obtain the desired product 4-(2,2,2-trifluoroethoxy)aniline with 97% yield and 99.9% purity. NMR, IR, MS, GC and other analysis and detection methods were used to conduct qualitative and quantitative analyses of the desired product. This paper discussed the process conditions of hydrogenation and reduction reaction and mainly investigated the impact of dosage and recycling of catalyst.
- Chen, Haiying,Lu, Ming,Shen, Jialin
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Read Online
- P-Aminophenyl alkyl ether-based 19F MRI probe for specific detection and imaging of hypochlorite ion
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We report a 19F MRI probe for the specific detection and imaging of -OCl. Our designed probe, having p-aminophenyl alkyl scaffold, reacted expeditiously with -OCl to produce a trifluoroethanol. Concomitant with the reaction, the 19F chemical shift changed by 2.6 ppm, allowing the visualization of -OCldependent probe-to-product conversion using 19F MRI.
- Doura, Tomohiro,An, Qi,Sugihara, Fuminori,Matsuda, Tetsuya,Sando, Shinsuke
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- 6-Amino[1,2,5]oxadiazolo[3,4- b]pyrazin-5-ol Derivatives as Efficacious Mitochondrial Uncouplers in STAM Mouse Model of Nonalcoholic Steatohepatitis
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Small molecule mitochondrial uncouplers have recently garnered great interest for their potential in treating nonalcoholic steatohepatitis (NASH). In this study, we report the structure-activity relationship profiling of a 6-amino[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ol core, which utilizes the hydroxy moiety as the proton transporter across the mitochondrial inner membrane. We demonstrate that a wide array of substituents is tolerated with this novel scaffold that increased cellular metabolic rates in vitro using changes in oxygen consumption rate as a readout. In particular, compound SHS4121705 (12i) displayed an EC50 of 4.3 μM in L6 myoblast cells and excellent oral bioavailability and liver exposure in mice. In the STAM mouse model of NASH, administration of 12i at 25 mg kg-1 day-1 lowered liver triglyceride levels and improved liver markers such as alanine aminotransferase, NAFLD activity score, and fibrosis. Importantly, no changes in body temperature or food intake were observed. As potential treatment of NASH, mitochondrial uncouplers show promise for future development.
- Salamoun, Joseph M.,Garcia, Christopher J.,Hargett, Stefan R.,Murray, Jacob H.,Chen, Sing-Young,Beretta, Martina,Alexopoulos, Stephanie J.,Shah, Divya P.,Olzomer, Ellen M.,Tucker, Simon P.,Hoehn, Kyle L.,Santos, Webster L.
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p. 6203 - 6224
(2020/07/14)
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- Properties of liquid crystals and Cu2+ recognition based on Schiff bases
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Two series of new Schiff base compounds were synthesized. For Schiff base compounds with a pyridine nitrogen atom in 4-position (7a-e), their supramolecular hydrogen bonding complexes show good liquid crystal properties. However, no liquid crystal property is observed for 8a-e. Results of theoretical calculations demonstrate that it is the intermolecular hydrogen bond of Schiff base compounds (8a-e) that prevents the formation of supramolecular hydrogen bonding. The Schiff base compounds, with terminal alkoxy chains, can recognize Cu2+ selectively with a color change. Nevertheless, others cannot recognize Cu2+.
- Liu, Zhilian,Yu, Zhenning,Zhang, Jian,Zhang, Shuxiang
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- Fuorinated hydrogen bonding liquid crystals based on Schiff base
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Two new Schiff base compounds, tailed by the fluoroalkoxy, were synthesized in a three-step process. Those supramolecular structures constructed by hydrogen bonding show good liquid crystal properties with higher clear points and wider mesomorphic phase ranges than other analogs containing a terminal alkoxy chain. Investigation of the optical textures by polarizing microscopy reveals that terminal fiuorinated substituents convert the nematic phase of supramolecular hydrogen-bonding complexes with terminal alkoxy chains into the smectic A phase of those with terminal fluoroalkoxy chains.
- Liu, Zhilian,Zhang, Jian,Li, Tengfei,Yu, Zhenning,Zhang, Shuxiang
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- FUSED HETEROCYCLIC COMPOUND AND APPLICATION THEREOF
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The present invention provides a compound useful for the prophylaxis or treatment of eicosanoid-associated diseases such as atherosclerosis, atherothrombosis, diabetes, obesity, asthma, fever, pain, cancer, rheumatism, osteoarthritis, atopic dermatitis and the like, and having superior pharmacological action, physicochemical properties and the like. The present invention relates to a compound represented by the following formula: wherein each symbol is as defined in the specification, or a salt thereof.
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Paragraph 0502; 0503
(2013/06/04)
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- NEW HEXAHYDROPYRROLOIMIDAZOLONE COMPOUNDS
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The invention provides novel compounds having the general formula (I), wherein R1, R2, R3 and A are as described herein, compositions including the compounds and methods of using the compounds. These compounds are useful as inhibitors of hormone sensitive
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Page/Page column 21
(2012/12/13)
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- NEW HEXAHYDROPYRROLOIMIDAZOLONE COMPOUNDS
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The invention provides novel compounds having the general formula (I) wherein R1, R2, R3 and A are as described herein, compositions including the compounds and methods of using the compounds.
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Page/Page column 53-54
(2012/12/13)
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- Fused ring compound and use thereof
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The present invention provides a compound represented by the formula: wherein the symbols are as described in the specification, or a salt thereof, which is useful for preventing/treating eicosanoid-associated diseases such as atherosclerosis, diabetes, obesity, atherothrombosis, asthma, fever, pain, cancer, rheumatism, osteoarthritis and atopic dermatitis, and which has an excellent pharmacological action, physicochemical properties, etc.
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Page/Page column 38
(2010/08/07)
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- AZACYCLIC SPIRODERIVATIVES AS HSL INHIBITORS
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Compounds of formula (I) as well as pharmaceutically acceptable salts thereof can be used in the form of pharmaceutical compositions, wherein n, m, A, R1 and R2 have the significance given in claim 1. The compounds are useful as HSL inhibitors for the treatment of diabetes dyslipidemia, atherosclerosis and obesity.
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Page/Page column 78
(2010/12/17)
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- RECEPTOR FUNCTION REGULATING AGENT
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The present invention relates to a GPR40 receptor function regulator comprising a fused imidazole compound represented by the formula: wherein each symbol is as defined in the specification, or a salt thereof or a prodrug thereof. The GPR40 receptor funct
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Page/Page column 61
(2010/11/28)
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- Piperidinyl-and piperazinyl-sulfonylmethyl hydroxamic acids and their use as protease inhibitors
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This invention is directed generally to proteinase (also known as “protease”) inhibitors, and, more particularly, to piperidinyl- and piperazinyl-sulfonylmethyl hydroxamic acids that, inter alia, inhibit matrix metalloproteinase (also known as “matrix metalloprotease” or “MMP”) activity and/or aggrecanase activity. Such hydroxamic acids generally correspond in structure to the following formula: (wherein A1, A2, Y, E1, E2, E3, and Rx are as defined in this specification), and further include salts of such compounds. This invention also is directed to compositions of such hydroxamic acids, intermediates for the syntheses of such hydroxamic acids, methods for making such hydroxamic acids, and methods for treating conditions (particularly pathological conditions) associated with MMP activity and/or aggrecanase activity.
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- CXCR3 antagonists
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Compounds, compositions and methods that are useful in the treatment of inflammatory and immune conditions and diseases are provided herein. In particular, the invention provides compounds which modulate the expression and/or function of a chemokine receptor. The subject methods are useful for the treatment of inflammatory and immunoregulatory disorders and diseases, such as multiple sclerosis, rheumatoid arthritis and type I diabetes.
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- Synthesis of 4-(1H,1H-perfluoroalkoxy )-4′-(6-methacryloyloxy-hexyloxy)-azobenzenes and their liquid crystalline intermediates
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The synthesis and characterization of 4-( 1H,1H-perfluoroalkoxy)-4′-(6-methacryloyloxy-hexyloxy)-azobenzenes with different lengths of the fluorinated tail group (C2-C8) and their liquid crystalline intermediates, starting from 1H,1H
- Thiele, Thomas,Prescher, Dietrich,Ruhmann, Ralf,Wolff, Dietmar
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p. 155 - 161
(2007/10/03)
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- Optically active antifungal azoles. VI. Synthesis and antifungal activity of N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl) propyl]-N′-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones and 5(1H,4H)-tetrazolones
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A new series of optically active antifungal azoles, N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl) propyl]-N′-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones (1,2) and 5(1H,4H)-tetrazolones (3), were prepared from the triflate derivative of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (13) by an SN2 displacement reaction with the union of an azolone (17-19) and subsequent ring-opening reaction with 1H-1,2,4-triazole. The optically active oxiranylethanol 13 was synthesized from methyl (R)-lactate in a stereocontrolled manner. The azolones 1-3 prepared showed potent antifungal activities in vitro and in vivo.
- Kitazaki, Tomoyuki,Tamura, Norikazu,Tasaka, Akihiro,Matsushita, Yoshihiro,Hayashi, Ryogo,Okonogi, Kenji,Itoh, Katsumi
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p. 314 - 327
(2007/10/03)
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- A Comparison between the Structure and Liquid-Crystalline Properties of 4-Cyano-4'-ethoxy- and 4-Cyano-4'-(2,2,2-trifluoroethoxy)-biphenyl
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The synthesis of 4-cyano-4'-(2,2,2-trifluoroethoxy)biphenyl (2OCBF3) is described and the melting point is found to be 20 deg C above that of 2OCB.The nematic-isotropic transition temperature for 2OCBF3 is determined to be lower than 30 deg C by extrapolation of the transition temperatures obtained for mixtures with the nematogen 135.The conformational distribution in 2OCBF3 is investigated by analysis with the maximum entropy method of the dipolar couplings obtained from the deuterium-decoupled, proton NMR spectrum of a partially-deuteriated sample dissolved in the nematic solvent ZLI 1132.It is concluded that 2OCB and 2OCBF3 have very similar conformational distributions, and that the differences in their phase transition temperatures is probably a consequence of the very different charge distributions in the two molecules.
- Emsley, James W.,Celebre, Giorgio,Luca, Giuseppina De,Longeri, Marcello,Catalano, Donata,Veracini, Carlo Alberto
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p. 429 - 434
(2007/10/03)
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- Liquid Crystals with Polar Substituents Containing Fluorine: Synthesis and Physical Properties
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Liquid crystalline compounds with various polar terminal groups containing fluorine have been prepared (see below formula 1 with Z = S-CHF2, S-CF3, SO-CHF2, SO-CF3, SO2-CHF2, SO2-CF3, SO2F, OCH2CF3, CO-OCH2CF3, CO-CF3, CO-CF2Cl, CO-CF2H, CO-CF2-CH3, CO-CF2-C3H7).The synthesis of these compounds is outlined here and their physical properties (phase transitions, dielectric anisotropy, birefringence, viscosity) are discussed.
- Bartmann, E.,Dorsch, D.,Finkenzeller, U.
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- Novel substituted aromatic compounds
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Substituted phenoxy, phenylthio and anilino compounds, intermediates therefor, synthesis thereof, and their use for the control of pests.
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- REGIOSELECTIVE FLUOROALKOXYLATION AND POLYFLUOROALKOXYLATION OF ACTIVATED POLYHALOBENZENES
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A series of activated polyhalobenzenes have been reacted with various amounts of sodium 2,2,2-trifluoroethoxide in DMF or HMPA.The nature of these monosubstitution and polysubstitution reactions are described.
- Gupton, John T.,Idoux, John P.,DeCrescenzo, Gary,Colon, Cesar
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p. 621 - 630
(2007/10/02)
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