50824-04-9Relevant articles and documents
Regioselective C-H Trifluoromethylation of Aromatic Compounds by Inclusion in Cyclodextrins
Lu, Xu,Kawazu, Ryohei,Song, Jizhou,Yoshigoe, Yusuke,Torigoe, Takeru,Kuninobu, Yoichiro
supporting information, p. 4327 - 4331 (2021/05/26)
A regioselective radical C-H trifluoromethylation of aromatic compounds was developed using cyclodextrins (CDs) as additives. The C-H trifluoromethylation proceeded with high regioselectivity to afford the product in good yield, even on the gram scale. In the presence of CDs, some substrates underwent a single trifluoromethylation selectively, whereas mixtures of single- and double-trifluoromethylated products were formed in the absence of the CD. 1H NMR experiments indicated that the regioselectivity was controlled by the inclusion of a substrate inside the CD cavity.
Regioselective monobromination of phenols with KBr and ZnAl–BrO3?–layered double hydroxides
Wang, Ligeng,Feng, Chun,Zhang, Yan,Hu, Jun
supporting information, (2020/02/22)
The regioselective mono-bromination of phenols has been successfully developed with KBr and ZnAl–BrO3?–layered double hydroxides (abbreviated as ZnAl–BrO3?–LDHs) as brominating reagents. The para site is much favorable and the ortho site takes the priority if para site is occupied. This reaction featured with excellent regioselectivity, cheap brominating reagents, mild reaction condition, high atom economy, broad substrate scope, and provided an efficient method to synthesize bromophenols.
Novel pleconaril derivatives: Influence of substituents in the isoxazole and phenyl rings on the antiviral activity against enteroviruses
Egorova, Anna,Ekins, Sean,Jahn, Birgit,Kazakova, Elena,Makarov, Vadim,Schmidtke, Michaela
, (2019/12/28)
Today, there are no medicines to treat enterovirus and rhinovirus infections. In the present study, a series of novel pleconaril derivatives with substitutions in the isoxazole and phenyl rings was synthesized and evaluated for their antiviral activity against a panel of pleconaril-sensitive and -resistant enteroviruses. Studies of the structure-activity relationship demonstrate the crucial role of the N,N-dimethylcarbamoyl group in the isoxazole ring for antiviral activity against pleconaril-resistant viruses. In addition, one or two substituents in the phenyl ring directly impact on the spectrum of antienteroviral activity. The 3-(3-methyl-4-(3-(3-N,N-dimethylcarbamoyl-isoxazol-5-yl)propoxy)phenyl)-5-trifluoromethyl-1,2,4-oxadiazole 10g was among the compounds exhibiting the strongest activity against pleconaril-resistant as well as pleconaril-susceptible enteroviruses with IC50 values from 0.02 to 5.25 μM in this series. Compound 10g demonstrated markedly less CYP3A4 induction than pleconaril, was non-mutagenic, and was bioavailable after intragastric administration in mice. These results highlight compound 10g as a promising potential candidate as a broad spectrum enterovirus and rhinovirus inhibitor for further preclinical investigations.
As the NS4B inhibitor benzofuran analogs (by machine translation)
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Paragraph 0094; 0096; 0097; 0098; 0099, (2016/10/31)
The present invention discloses a kind of as NS4B benzofuran analogue inhibitors, in particular to the formula (I) below or a pharmaceutically acceptable salt thereof. (by machine translation)
Hepatitis C replication inhibitors that target the viral NS4B protein
Miller, John F.,Chong, Pek Y.,Shotwell, J. Brad,Catalano, John G.,Tai, Vincent W.-F.,Fang, Jing,Banka, Anna L.,Roberts, Christopher D.,Youngman, Michael,Zhang, Huichang,Xiong, Zhiping,Mathis, Amanda,Pouliot, Jeffery J.,Hamatake, Robert K.,Price, Daniel J.,Seal, John W.,Stroup, Lisa L.,Creech, Katrina L.,Carballo, Luz H.,Todd, Dan,Spaltenstein, Andrew,Furst, Sylvia,Hong, Zhi,Peat, Andrew J.
supporting information, p. 2107 - 2120 (2014/04/03)
We describe the preclinical development and in vivo efficacy of a novel chemical series that inhibits hepatitis C virus replication via direct interaction with the viral nonstructural protein 4B (NS4B). Significant potency improvements were realized through isosteric modifications to our initial lead 1a. The temptation to improve antiviral activity while compromising physicochemical properties was tempered by the judicial use of ligand efficiency indices during lead optimization. In this manner, compound 1a was transformed into (+)-28a which possessed an improved antiviral profile with no increase in molecular weight and only a modest elevation in lipophilicity. Additionally, we employed a chimeric "humanized" mouse model of HCV infection to demonstrate for the first time that a small molecule with high in vitro affinity for NS4B can inhibit viral replication in vivo. This successful proof-of-concept study suggests that drugs targeting NS4B may represent a viable treatment option for curing HCV infection.
BIARYL DERIVATIVES AS GPR120 AGONISTS
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Paragraph 541; 542; 543, (2015/01/16)
The present invention relates to biaryl derivatives of Formula 1, a method for preparing the same, a pharmaceutical composition comprising the same and use thereof. The biaryl derivatives of Formula 1 according to the present invention promote GLP-1 formation in the gastrointestinal tract and improve insulin resistance in the liver or in muscle due to anti-inflammatory action in macrophages, lipocytes, etc., and can accordingly be effectively used for preventing or treating diabetes, complications of diabetes, obesity, non-alcoholic fatty liver, steatohepatitis, osteoporosis or inflammation.
P-Hydroxyphenacyl photoremovable protecting groups Robust photochemistry despite substituent diversity
Givens, Richard S.,Stensrud, Kenneth,Conrad, Peter G.,Yousef, Abraham L.,Perera, Chamani,Senadheera, Sanjeewa N.,Heger, Dominik,Wirz, Jakob
scheme or table, p. 364 - 384 (2011/06/22)
A broadly based investigation of the effects of a diverse array of substituents on the photochemical rearrangement of p-hydroxyphenacyl esters has demonstrated that common substituents such as F, MeO, CN, CO2R, CONH2, and CH3 have little effect on the rate and quantum efficiencies for the photo-Favorskii rearrangement and the release of the acid leaving group or on the lifetimes of the reactive triplet state. A decrease in the quantum yields across all substituents was observed for the release and rearrangement when the photolyses were carried out in buffered aqueous media at pHs that exceeded the ground-state pKa of the chromophore where the conjugate base is the predominant form. Otherwise, substituents have only a very modest effect on the photoreaction of these robust chromophores.
2-PYRIDONE COMPOUNDS
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Page/Page column 85, (2011/10/12)
A 2-pyridone compound represented by the formula [1]: {wherein in the formula [1], the ring represented by A represents a benzene ring or a pyridine ring, X represents any of the structures represented by the formulas [3] shown below: V represents a single bond or a lower alkylene group, and W represents a single bond, an ether bond or a lower alkylene group (wherein the lower alkylene group may contain an ether bond)}, a tautomer or stereoisomer of the compound, a pharmaceutically acceptable salt thereof, or a solvate thereof is a compound that has an excellent GK activating effect and is useful as a pharmaceutical.
PYRIMIDINE INHIBITORS OF KINASE ACTIVITY
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Page/Page column 90, (2010/12/26)
The present invention relates to compounds of formula (I) or pharmaceutical acceptable salts or solvates thereof, wherein G1, R2, R3, R4, R5, n, p, q, Ar1, and Ar2 are defined in the description. The present invention relates also to methods of making said compounds, and compositions comprising said compounds which are useful for inhibiting kinases such as IGF-IR.
Novel liquid-crystalline mesogens and main-chain chiral smectic thiol-ene polymers based on trifluoromethylphenyl moieties
Yang, Hong,Wang, Lixing,Shao, Renfan,Clark, Noel A.,Ortega, Josu,Etxebarria, Jesus,Albouy, Pierre-Antoine,Walba, David M.,Keller, Patrick
scheme or table, p. 7208 - 7215 (2010/05/18)
The synthesis and characterization of a series of novel liquid-crystalline molecules containing a trifluoromethylphenyl core or a 2,3-bis(trifluoromethyl) phenyl core is described. All trifluoromethylphenyl-containing compounds (W530, W551, and W558) have mesomorphic properties while 2,3-bis(trifluoromethyl) phenyl-containing compounds (W555, W556, W557) are room-temperature crystals without mesophases. Thereafter, based on the chemical structure of W558, to pursue a mesogen with a large electroclinic effect in the SmA* phase for development into electromechanical actuators, a chiral smectic thiol-ene monomer (K0901) is synthesized and polymerized in organic solvents. The polymer is characterized by GPC, DSC, PLM, XRD and shows an expected I-SmA* -Glass phase sequence though the electroclinic effect is relatively small.
