14703-69-6Relevant articles and documents
Characterization of a New Electron Donor-Acceptor Dyad in Conventional Solvents and Ionic Liquids
Saladin, Marissa,Rumble, Christopher A.,Wagle, Durgesh V.,Baker, Gary A.,Maroncelli, Mark
, p. 9395 - 9407 (2019)
Ionic liquids are being tested as potential replacements for current electrolytes in energy-related applications. Electron transfer (ET) plays a central role in these applications, making it essential to understand how ET in ionic liquids differs from ET in conventional organic solvents and how these differences affect reaction kinetics. A new intramolecular electron donor-acceptor probe was synthesized by covalently linking the popular photoacceptor coumarin 152 with the donor dimethylaniline to create the dyad "C152-DMA" for potential use in probing dynamical solvent effects in ionic liquids. Molecular dynamics simulations of this dyad show the considerable conformational flexibility of the linker group but over a range of geometries in which the ET rate parameters vary little and should have minimal effect on reaction times >100 ps. Steady-state and time-resolved fluorescence methods show the spectra of C152-DMA to be highly responsive to solvent polarity, with ET rates varying over the range of 108 to 1012 s-1 between nonpolar and high-polarity conventional solvents. The sensitivity to hydrolysis in the presence of acidic impurities limits the dyad's use to ionic liquids of high purity. The results in the few ionic liquids examined here suggest that in addition to solvent polarity, electron transfer in C152-DMA also depends on solvent fluidity or solvation times.
Adduct ion formation by aromatic amines in thermospray mass spectrometry
Honing, Maarten,Barcelo, Damia,Van Baar, Ben L. M.,Brinkman, Udo A. Th.
, p. 527 - 536 (1996)
The formation of solvent adduct ions in thermospray and ionspray mass spectrometry was studied for twelve aromatic amines: aniline, N-methylaniline, N,N-dimethylaniline, 3-aminophenol, 3-methylaminophenol, 3-dimethylaminophenol, 2-aminopyridine, 2-methyla
Discovery of a novel and potent inhibitor with differential species-specific effects against NLRP3 and AIM2 inflammasome-dependent pyroptosis
Bin, Huachao,Cao, Zhixing,Chen, Pei,Jiao, Yan,Li, Linli,Lin, Guifeng,Lin, Wanting,Mu, Bo,Nan, Jinshan,Pan, Shulei,Pan, Zhiling,Wang, Falu,Xia, Anjie,Yang, Shengyong,Yang, Shunhua,Zhang, Shanshan,Zhang, Yun,Zhou, Nenghua
, (2022/02/21)
The NLRP3 inflammasome, which regulated a proinflammatory programmed cell death form termed pyroptosis, is involved in the pathological process of various human diseases, such as multiple sclerosis, type 2 diabetes, and gout. Thus, compounds inhibiting activation of the NLRP3 inflammasome can be promising treatments for these diseases. In this study, we conducted a phenotypic screening against NLRP3-dependent pyroptosis and discovered the hit compound 1, which showed moderate antipyroptotic activity. Chemistry efforts to improve potency of 1 resulted in a novel compound 59 (J114), which exhibited a half-maximal inhibitory concentration (IC50) of 0.077 ± 0.008 μM against cell pyroptosis. Interestingly, unlike all pyroptosis inhibitors currently reported, the activity of J114 showed significant differences in human- and mouse-derived cells. The IC50 of J114-mediated inhibition of IL-1β secretion by human THP-1 macrophages was 0.098 μM, which was nearly 150-fold and 500-fold more potent than that of J774A.1 (14.62 μM) and bone marrow-derived macrophages (BMDMs) (48.98 μM), respectively. Further studies showed that J114 displayed remarkable inhibitory activity against NLRP3- and AIM2-but not NLRC4-dependent activation of caspase-1 and the release of IL-1β in human THP-1 macrophages. Mechanistically, J114 disturbed the interaction of NLRP3 or AIM2 with the adaptor protein ASC and inhibited ASC oligomerization. Overall, our study identified a unique molecule that inhibits NLRP3 and AIM2 inflammasome activation and has species differences, which is worthy of further research to understand the differential regulation of the NLRP3 and AIM2 inflammasomes in humans and mice.
The discovery of 2-substituted phenol quinazolines as potent RET kinase inhibitors with improved KDR selectivity
Newton, Rebecca,Bowler, Katherine A.,Burns, Emily M.,Chapman, Philip J.,Fairweather, Emma E.,Fritzl, Samantha J.R.,Goldberg, Kristin M.,Hamilton, Niall M.,Holt, Sarah V.,Hopkins, Gemma V.,Jones, Stuart D.,Jordan, Allan M.,Lyons, Amanda J.,Nikki March,McDonald, Neil Q.,Maguire, Laura A.,Mould, Daniel P.,Purkiss, Andrew G.,Small, Helen F.,Stowell, Alexandra I.J.,Thomson, Graeme J.,Waddell, Ian D.,Waszkowycz, Bohdan,Watson, Amanda J.,Ogilvie, Donald J.
, p. 20 - 32 (2016/02/19)
Deregulation of the receptor tyrosine kinase RET has been implicated in medullary thyroid cancer, a small percentage of lung adenocarcinomas, endocrine-resistant breast cancer and pancreatic cancer. There are several clinically approved multi-kinase inhibitors that target RET as a secondary pharmacology but additional activities, most notably inhibition of KDR, lead to dose-limiting toxicities. There is, therefore, a clinical need for more specific RET kinase inhibitors. Herein we report our efforts towards identifying a potent and selective RET inhibitor using vandetanib 1 as the starting point for structure-based drug design. Phenolic anilinoquinazolines exemplified by 6 showed improved affinities towards RET but, unsurprisingly, suffered from high metabolic clearance. Efforts to mitigate the metabolic liability of the phenol led to the discovery that a flanking substituent not only improved the hepatocyte stability, but could also impart a significant gain in selectivity. This culminated in the identification of 36; a potent RET inhibitor with much improved selectivity against KDR.
Development of trifunctional probes for glycoproteomic analysis
Tsai, Charng-Sheng,Liu, Po-Yu,Yen, Hsin-Yung,Hsu, Tsui-Ling,Wong, Chi-Huey
supporting information; experimental part, p. 5575 - 5577 (2010/09/18)
A new trifunctional probe, assembled using a cleavable linker, is useful for efficient enrichment and detection of alkynyl sugar-tagged biomolecules. The Royal Society of Chemistry 2010.
An optically uniaxial antiferroelectric smectic phase in asymmetrical bent-core compounds containing a 3-aminophenol central unit
Gomola, Kinga,Guo, Lingfeng,Pociecha, Damian,Araoka, Fumito,Ishikawa, Ken,Takezoe, Hideo
scheme or table, p. 7944 - 7952 (2011/04/26)
Two new series of asymmetrical bent-core compounds possessing 3-aminophenol and its N-methyl derivative were synthesized. In the obtained compounds, the asymmetry comes from the different linkages between the central unit and its arms and in two cases also from different lateral substituents. The mesomorphic properties were investigated by differential scanning calorimetry, polarizing optical microscopy, switching current and electro-optical measurements, X-ray analysis, and second-harmonic generation. All materials possessing 3-aminophenol as a central unit showed liquid crystalline properties, and two of them exhibited the orthogonal smectic phase (SmA family phase) and very stable columnar phases, while the N-methyl analogues exhibited no mesophase. Because of the optically uniaxial nature, double switching current peaks, and SHG activity associated with a distinct threshold electric field, this orthogonal smectic phase is assigned to a novel type, which has a short-range antiferroelectric order with a long-range randomized polar plane (SmAPAR). This is very unique in the sense that distinct threshold behavior emerges at the field-induced phase transition from the short-range antiferroelectric phase to a long-range ferroelectric phase.
Synthesis of mono-N-substituted functionalized anilines
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Page 3, (2008/06/13)
The present invention relates to a process for direct and selective synthesis of mono-N-substituted functionalized anilines by using alkylating agents selected from the class of organic carbonates, preferably of the dialkyl, dibenzyl and diallyl types, in the presence of suitable catalysts that are chemically related to the class of aluminosilicates.
Synthesis of mono-N-substituted functionalized anilines
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Page 5, (2008/06/13)
The present invention relates to a process for direct and selective synthesis of mono-N-substituted functionalized anilines by using alkylating agents selected from the class of organic carbonates, preferably of the dialkyl, dibenzyl and diallyl types, in the presence of suitable catalysts that are chemically related to the class of aluminosilicates.
FLUORENES AND ANTHRACENES THAT INHIBIT P2X3 AND P2X2/3 CONTAINING RECEPTORS
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Page/Page column 9-10, (2008/06/13)
Compounds of formula (I) are novel P2X3 and P2X2/P2X3 containing receptor antagonists and are useful in treating pain, urinary incontinence, and bladder overactivity.
Reaction of functionalized anilines with dimethyl carbonate over NaY faujasite. 3. Chemoselectivity toward mono-N-methylation
Selva, Maurizio,Tundo, Pietro,Perosa, Alvise
, p. 7374 - 7378 (2007/10/03)
In the presence of NaY faujasite, dimethyl carbonate (MeOCO2Me, DMC) is a highly chemoselective methylating agent of functionalized anilines such as aminophenols (1), aminobenzyl alcohols (2), aminobenzoic acids (3), and aminobenzamides (4). The reaction proceeds with the exclusive formation of N-methylanilines without any concurrent O-methylation or N-/O-methoxy carbonylation side processes. Particularly, only mono-N-methyl derivatives [XC6H4NHMe, X = o-, m-, and p-OH; o- and p-CH 2OH; o- and P-CO2H; o- and p-CONH2] are obtained with selectivity up to 99% and isolated yields of 74-99%. DMC, which usually promotes methylations only at T > 120 °C, is activated by the zeolite catalyst and it reacts with compounds 1, 2, and 4, at 90 °C. Aminobenzoic acids (3) require a higher reaction temperature (≥130 °C).
