- ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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The present application relates to an organic electroluminescent compound represented by chemical formula 1, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present application having good thermal stability, it is possible to provide the organic electroluminescent device having lower driving voltage, high luminous efficiency and/or long lifespan characteristics compared with an existing organic electroluminescent device.COPYRIGHT KIPO 2020
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Paragraph 0158-0161
(2020/05/01)
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- Design, synthesis and biological evaluation of novel 4-phenoxypyridine based 3-oxo-3,4-dihydroquinoxaline-2-carboxamide derivatives as potential c-Met kinase inhibitors
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Blocking c-Met kinase activity by small-molecule inhibitors has been identified as a promising approach for the treatment of cancers. Herein, we described the design, synthesis, and biological evaluation of a series of 4-phenoxypyridine-based 3-oxo-3,4-dihydroquinoxaline derivatives as c-Met kinase inhibitors. Inhibitory activitives against c-Met kinase evaluation indicated that most of compounds showed excellent c-Met kinase activity in vitro, and IC50 values of ten compounds (23a, 23e, 23f, 23l, 23r, 23s, 23v, 23w, 23x and 23y) were less than 10.00 nM. Notably, three of them (23v, 23w and 23y) showed remarkable potency with IC50 values of 2.31 nM, 1.91 nM and 2.44 nM, respectively, and thus they were more potent than positive control drug foretinib (c-Met, IC50 = 2.53 nM). Cytotoxic evaluation indicated the most promising compound 23w showed remarkable cytotoxicity against A549, H460 and HT-29 cell lines with IC50 values of 1.57 μM, 0.94 μM and 0.65 μM, respectively. Furthermore, the acridine orange/ethidium bromide (AO/EB) staining, cell apoptosis assays by flow cytometry, wound-healing assays and transwell migration assays on HT-29 and/or A549 cells of 23w were performed. Especially compound 23w, which displayed potent antitumor, apoptosis induction and antimetastatic activity, could be used as a promising lead for further development. Meanwhile, their preliminary structure-activity relationships (SARs) were also discussed.
- Wang, Zhen,Shi, Jiantao,Zhu, Xianglong,Zhao, Wenwen,Gong, Yilin,Hao, Xuechen,Hou, Yunlei,Liu, Yajing,Ding, Shi,Liu, Ju,Chen, Ye
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- Design, synthesis and biological evaluation of novel 4-phenoxyquinoline derivatives containing 3-oxo-3,4-dihydroquinoxaline moiety as c-Met kinase inhibitors
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A series of novel 4-phenoxyquinoline derivatives containing 3-oxo-3,4-dihydroquinoxaline moiety were synthesized and evaluated for their c-Met kinase inhibitory activity and antiproliferative activity against five cancer cell lines (HT-29, H460, A549, MKN-45 and U87MG) in vitro. Most of the compounds exhibited moderate-to-significant cytotoxicity as compared with foretinib. The most promising compound 41 (with c-Met IC50 value of 0.90?nM) showed remarkable cytotoxicity against HT-29, H460, A549, MKN-45 and U87MG cell lines with IC50 values of 0.06?μM, 0.05?μM, 0.18?μM, 0.023?μM and 0.66?μM, respectively, and thus it was 1.22- to 3.50-fold more potent than foretinib. Their preliminary structure-activity relationships (SARs) studies indicate that electron-withdrawing groups on the terminal phenyl rings are beneficial for improving the antitumor activity.
- Liu, Ju,Yang, Di,Yang, Xiuxiu,Nie, Minhua,Wu, Guodong,Wang, Zhunchao,Li, Wei,Liu, Yajing,Gong, Ping
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p. 4475 - 4486
(2017/07/22)
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- MULTICYCLIC COMPOUND INCLUDING NITROGEN AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME
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The present invention relates to a polycyclic compound containing nitrogen, and an organic light emitting device comprising the same. The organic light emitting device of the present invention comprises a positive electrode, a negative electrode, and one
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Paragraph 0120-0123
(2016/10/10)
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- Apparent alkyl transfer and phenazine formation via an aryne intermediate
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Treatment of chlorotriaryl derivatives 3a and 3d or fluorotriaryl derivatives 3b and 3e with potassium diisopropylamide afforded alkyl-shifted phenazine derivatives 5a/5b, rather than the expected 9-membered triazaorthocyclophane 2a. The phenazine derivatives were isolated in 78-98% yield depending on the halogen and alkyl group present. In the absence of the halogen (chloro or fluoro), the apparent alkyl shift proceeds more slowly and cannot proceed via the intermediacy of the aryne intermediate. Mechanistic possibilities include intramolecular nucleophilic attack on an aryne intermediate leading to a zwitterionic intermediate and alkyl transfer via a 5-endo-tet process, or via a Smiles rearrangement.
- Panagopoulos, Andria M.,Steinman, Doug,Goncharenko, Alexandra,Geary, Kyle,Schleisman, Carlene,Spaargaren, Elizabeth,Zeller, Matthias,Becker, Daniel P.
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p. 3532 - 3540
(2013/06/04)
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- Synthesis of an ortho-triazacyclophane: N, N ′, N ″-trimethyltribenzo-1,4,7-triazacyclononatriene
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N,N′,N″-Trimethyltribenzo-1,4,7-triazacyclononatriene has been synthesized via sequential palladium-catalyzed Buchwald-Hartwig N-arylation reactions affording the 9-membered triaza o-cyclophane in 35% overall yield. An X-ray crystal structure shows the ne
- Panagopoulos, Andria M.,Zeller, Matthias,Becker, Daniel P.
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experimental part
p. 7887 - 7892
(2011/02/25)
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- Supramolecular Scaffolds and Methods of Making the Same
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Tribenzo-1,4,7-triazacyclononane and derivatives thereof having a formula (I) are disclosed. Methods of making tribenzo-1,4,7-triazacyclononane and related compounds also are disclosed.
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Page/Page column 10
(2010/03/04)
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- Discovery of novel selective norepinephrine reuptake inhibitors: 4-[3-Aryl-2,2-dioxido-2,1,3-benzothiadiazol-1(3 H)-yl]-1-(methylamino)butan-2- ols (WYE-103231)
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Structural modification of a virtual screening hit led to the identification of a new series of 4-[3-aryl-2,2-dioxido-2,1,3-benzothiadiazol- 1(3H)-yl]-1-(methylamino)butan-2-ols which are potent and selective inhibitors of the norepinephrine transporter over both the serotonin and dopamine transporters. One representative compound S-17b (WYE-103231) had low nanomolar hNET potency (IC50 = 1.2 nM) and excellent selectivity for hNET over hSERT (>1600-fold) and hDAT (>600-fold). S-17b additionally had a good pharmacokinetic profile and demonstrated oral efficacy in rat models of ovariectomized-induced thermoregulatory dysfunction and morphine dependent flush as well as the hot plate and spinal nerve ligation (SNL) models of acute and neuropathic pain.
- O'Neill, David J.,Adedoyin, Adedayo,Alfinito, Peter D.,Bray, Jenifer A.,Cosmi, Scott,Deecher, Darlene C.,Fensome, Andrew,Harrison, Jim,Leventhal, Liza,Mann, Charles,McComas, Casey C.,Sullivan, Nicole R.,Spangler, Taylor B.,Uveges, Albert J.,Trybulski, Eugene J.,Whiteside, Garth T.,Zhang, Puwen
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experimental part
p. 4511 - 4521
(2010/08/20)
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- ARYL SULFAMIDE DERIVATIVES AND METHODS OF THEIR USE
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The present invention is directed to aryl sulfamide derivatives of formula (I): or a pharmaceutically acceptable salt, stereoisomer or tautomer thereof, which are monoamine reuptake inhibitors, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions, including, inter alia, vasomotor symptoms, sexual dysfunction, gastrointestinal disorders and genitourinary disorder, depression disorders, endogenous behavioral disorders, cognitive disorders, diabetic neuropathy, pain, and other diseases or disorders.
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Page/Page column 143
(2008/12/06)
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- From the study of naturally occurring N-allylated phenazines towards new Pd-mediated transformations
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New Pd-mediated reductive heteroannulations of N-allyl diphenylamines accessible through Pd-catalyzed N-arylation and of O-allylethers are reported.
- Meri?or, Elena,Beifuss, Uwe
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p. 8383 - 8387
(2008/03/14)
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- Efficient methods for the synthesis of 2-hydroxyphenazine based on the Pd-catalyzed N-arylation of aryl bromides
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(Chemical Equation Presented) Substituted diphenylamines can be synthesized by Pd(0)-catalyzed N-arylation using o-nitroanilines and nitro-substituted aryl bromides for a substrate. Cyclization of the diphenylamines by various methods, including the intramolecular Pd(0)-catalyzed N-arylation, produces 2-methoxyphenazine which can easily be deprotected to give 2-hydroxyphenazine. This phenazine is required to synthesize methanophenazine, a novel redoxactive cofactor isolated from methanogenic archaea.
- Tietze, Mario,Iglesias, Alberto,Merisor, Elena,Conrad, Juergen,Klaiber, Iris,Beifuss, Uwe
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p. 1549 - 1552
(2007/10/03)
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- An improved synthesis of N-substituted-2-nitroanilines
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The reaction of 2-chloronitrobenzene with substituted amines/ anilines in the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) gives N-substituted-2-nitroanilines in good to excellent yields (>75-90%).
- Chauhan,Singh, Ram,Geetanjali
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p. 2899 - 2906
(2007/10/03)
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- Electrochemical Reactions. Part 24. Reductive Cyclisation of i-(2-Halogenophenyl)-j-phenyl Compounds: A General Reaction
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The phenyl ?-radical formed by reduction of aryl halides in an aprotic solvent undergoes efficient radical substitution on an adjacent benzene ring.Several examples of this cyclisation reaction are given.The reaction is appropriate for the synthesis of 6-membered aromatic rings where the two reacting phenyl groups are held in a cis-configuration by an olefin bond or another aromatic ring.
- Grimshaw, James,Hamilton, Robert,Trocha-Grimshaw, Jadwiga
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p. 229 - 234
(2007/10/02)
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