39263-32-6Relevant articles and documents
Synthesis, characterization, and SAR of arylated indenoquinoline-based cholinesterase and carbonic anhydrase inhibitors
Ekiz, Makbule,Tutar, Ahmet,?kten, Salih,Bütün, Burcu,Ko?yi?it, ümit M.,Taslimi, Parham,Top?u, Güla?t?
, (2018)
We report the synthesis of bromoindenoquinolines (15a–f) by Friedlander reactions in low yields (13–50%) and the conversion of the corresponding phenyl-substituted indenoquinoline derivatives 16–21 in high yields (80–96%) by Suzuki coupling reactions. To explore the structure–activity relationship (SAR), their inhibition potentials to inhibit acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human carbonic anhydrase cyctosolic (hCA I and II) enzymes were determined. Monophenyl (16–18) indenoquinolines significantly inhibited the AChE and BChE enzymes in ranges of IC50 37–57 nM and 84–93 nM, respectively, compared with their starting materials 15a–c and reference compounds (galanthamine and tacrine). On the other hand, these novel arylated indenoquinoline-based derivatives were effective inhibitors of the BChE, hCA I and II, BChE and AChE enzymes with Ki values in the range of 37 ± 2.04 to 88640 ± 1990 nM for AChE, 120.94 ± 37.06 to 1150.95 ± 304.48 nM for hCA I, 267.58 ± 98.05 to 1568.16 ± 438.67 nM for hCA II, and 84 ± 3.86 to 144120 ± 2910 nM for BChE. As a result, monophenyl indenoquinolines 16–18 may have promising anti-Alzheimer drug potential and 3,8-dibromoindenoquinoline amine (15f) can be novel hCA I and hCA II enzyme inhibitors.
A Practical Procedure for Regioselective Bromination of Anilines
Takahashi, Yusuke,Seki, Masahiko
, p. 1828 - 1832 (2021/04/15)
A highly practical procedure for the preparation of bromoanilines by using copper-catalyzed oxidative bromination has been developed. Treatment of free anilines with readily available NaBr and Na 2S 2O 8in the presence of a catalytic amount of CuSO 4·5H 2O enabled regioselective bromination.
METHOD FOR PRODUCING AROMATIC HALOGEN DERIVATIVE
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Paragraph 0145-0148, (2020/07/28)
PROBLEM TO BE SOLVED: To provide a highly efficient and economically advantageous method for producing a halogen compound. SOLUTION: The method produces a halogen compound represented by formula (2) (X is a halogen atom, and b is an integer of 1-5) by reacting an aniline derivative represented by formula (1) (R1 is an ester group, a carbonyl group, a nitrile group, a nitro group, an optionally substituted alkyl group or an optionally substituted aralkyl group, and a is an integer of 0-4) with a halogenating agent in the presence of a copper catalyst and a persulfate. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
NOVEL ORGANIC HETEROCYCLIC COMPOUND AND LIGHT-EMITTING DEVICE COMPRISING SAME
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Paragraph 0120-0121, (2018/03/28)
The present invention relates to an organic light-emitting compound represented by [Chemical Formula A] and an organic light-emitting device. In Chemical Formula, A, X, Y, Z, and the substituents R1 to R8, and R11 to R20 are as defined in the specification.
o-xylylene bis(triethyl ammonium tribromide) as a mild and recyclable reagent for rapid and regioselective bromination of anilines and phenols
Hemati, Roya,Shahvelayati, Ashraf S.,Yadollahzadeh, Khadijeh
, p. 682 - 687 (2018/07/14)
Background: o-Xylylene bis(triethyl ammonium tribromide) (OXBTEATB) as a recyclable and high bromine containing di-(tribromide) reagent has been employed for the bromination of various organic substrates such as phenol and aniline or its derivatives. This catalyst can be recovered and reused several times. Methods: Aryl bromides shown in Table 1, were easily produced from bromination of aromatic compounds by OXBTEATB. This high-yield process lets the reagents to be recycled and reused. Results: As shown in Table 1, substituted anilines, phenols and β-naphthol were found to be the most reactive and immediately converted to the corresponding mono-brominated products by OXBTEATB. Conclusion: OXBTEATB can be considered a solidified bromine. This novel reagent has variable solubility in different polar protic and aprotic solvents but insoluble in non-polar aprotic solvent. Subsequently, OXBTEATB can be recognized as a more useful brominating and regioselective catalyst than the liquid bromine.
Catalytic Reductive Synthesis and Direct Derivatization of Unprotected Aminoindoles, Aminopyrroles, and Iminoindolines
Leijendekker, Leonardus H.,Weweler, Jens,Leuther, Tobias M.,Streuff, Jan
supporting information, p. 6103 - 6106 (2017/05/22)
A titanium(III)-catalyzed radical cyclization to unprotected 3-aminoindoles, 3-aminopyrroles, or 3-iminoindolines is reported. The reaction is non-hazardous, scalable, and allows facile isolation of the free products by extraction. The method is demonstrated on a large substrate scope and it further allows the direct installation of various nitrogen protecting groups or the synthesis of building blocks for peptide chemistry in a single sequence. Fused bisindoles can be directly accessed from the cyclization products.
Sulfonamides as Selective NaV1.7 Inhibitors: Optimizing Potency, Pharmacokinetics, and Metabolic Properties to Obtain Atropisomeric Quinolinone (AM-0466) that Affords Robust in Vivo Activity
Graceffa, Russell F.,Boezio, Alessandro A.,Able, Jessica,Altmann, Steven,Berry, Loren M.,Boezio, Christiane,Butler, John R.,Chu-Moyer, Margaret,Cooke, Melanie,DiMauro, Erin F.,Dineen, Thomas A.,Feric Bojic, Elma,Foti, Robert S.,Fremeau, Robert T.,Guzman-Perez, Angel,Gao, Hua,Gunaydin, Hakan,Huang, Hongbing,Huang, Liyue,Ilch, Christopher,Jarosh, Michael,Kornecook, Thomas,Kreiman, Charles R.,La, Daniel S.,Ligutti, Joseph,Milgram, Benjamin C.,Lin, Min-Hwa Jasmine,Marx, Isaac E.,Nguyen, Hanh N.,Peterson, Emily A.,Rescourio, Gwen,Roberts, John,Schenkel, Laurie,Shimanovich, Roman,Sparling, Brian A.,Stellwagen, John,Taborn, Kristin,Vaida, Karina R.,Wang, Jean,Yeoman, John,Yu, Violeta,Zhu, Dawn,Moyer, Bryan D.,Weiss, Matthew M.
, p. 5990 - 6017 (2017/08/02)
Because of its strong genetic validation, NaV1.7 has attracted significant interest as a target for the treatment of pain. We have previously reported on a number of structurally distinct bicyclic heteroarylsulfonamides as NaV1.7 inhibitors that demonstrate high levels of selectivity over other NaV isoforms. Herein, we report the discovery and optimization of a series of atropisomeric quinolinone sulfonamide inhibitors [ Bicyclic sulfonamide compounds as sodium channel inhibitors and their preparation. WO 2014201206, 2014 ] of NaV1.7, which demonstrate nanomolar inhibition of NaV1.7 and exhibit high levels of selectivity over other sodium channel isoforms. After optimization of metabolic and pharmacokinetic properties, including PXR activation, CYP2C9 inhibition, and CYP3A4 TDI, several compounds were advanced into in vivo target engagement and efficacy models. When tested in mice, compound 39 (AM-0466) demonstrated robust pharmacodynamic activity in a NaV1.7-dependent model of histamine-induced pruritus (itch) and additionally in a capsaicin-induced nociception model of pain without any confounding effect in open-field activity.
Heterocyclic compound and organic light-emitting device comprising the same
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Paragraph 0401-0403, (2016/10/08)
Disclosed are a heterocyclic compound and an organic light-emitting device comprising the same. The heterocyclic compound is represented by chemical formula 1. The organic light-emitting device comprising the heterocyclic compound can have low driving voltage, high brightness, high efficiency, and long lifespan.COPYRIGHT KIPO 2016
ARYL AMIDE KINASE INHIBITORS
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Page/Page column 187; 188, (2015/02/02)
The present disclosure is generally directed to compounds which can inhibit AAK1 (adaptor associated kinase 1), compositions comprising such compounds, and methods for inhibiting AAK1.
An organoelectro luminescent compounds and organoelectro luminescent device using the same
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Paragraph 0316-0318, (2016/10/10)
The present invention relates to an organic light emitting compound represented by chemical formula 1, and to an organic electroluminescent device comprising the same. The organic electroluminescent device applying the organic light emitting compound according to the present invention is driven with a low voltage, improved light emitting efficiency, and high durability compared with a device applying an existing material.
