322-78-1Relevant academic research and scientific papers
Design, synthesis and biological evaluation of novel 4-phenoxypyridine based 3-oxo-3,4-dihydroquinoxaline-2-carboxamide derivatives as potential c-Met kinase inhibitors
Wang, Zhen,Shi, Jiantao,Zhu, Xianglong,Zhao, Wenwen,Gong, Yilin,Hao, Xuechen,Hou, Yunlei,Liu, Yajing,Ding, Shi,Liu, Ju,Chen, Ye
, (2020)
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.
Biomimetic alloxan-catalyzed intramolecular redox reaction with O2: One-pot atom-economic synthesis of sulfinyl-functionalized benzimidazoles
Zhang, Shiqi,Yi, Dong,Li, Guangxun,Li, Ling,Zhao, Gang,Tang, Zhuo
supporting information, (2020/12/25)
Given the necessity of sacrificial reductants in various biomimetic aerobic oxygenations, alloxan-catalyzed aerobic redox system for one-pot atom-economic synthesis of sulfinyl-functionalized benzimidazoles was developed by ingeniously binding both the substrate sulfide and sacrificial reductant. This mild and transition-metal-free protocol undergoes two oxidations without additional sacrificial reagents, except for the environmentally benign molecular oxygen.
Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source
Qi, Xinxin,Zhou, Rong,Peng, Jin-Bao,Ying, Jun,Wu, Xiao-Feng
supporting information, p. 5161 - 5164 (2019/01/25)
A selenium-catalyzed carbonylative reaction for the synthesis of 2-benzimidazolones from 2-nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene-1,3,5-triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2-benzimidazolones were produced in moderate to excellent yields.
Organometallic Ir(III) Phosphors Decorated by Carbazole/Diphenylphosphoryl Units for Efficient Solution-Processable OLEDs with Low Efficiency Roll-Offs
Song, Wei-Lin,Mao, Hui-Ting,Shan, Guo-Gang,Gao, Ying,Cheng, Gang,Su, Zhong-Min
supporting information, p. 13807 - 13814 (2019/10/14)
Recently, solution-processable PhOLEDs have been attracting great interest for their low cost and high productivity relative to the vacuum-deposited devices. Similar to vacuum-deposited OLEDs, however, they usually suffer from serious efficiency roll-offs, especially in high brightness. Finding a feasible way and/or designing novel materials to increase efficiencies and reduce roll-offs simultaneously are highly desired. Herein, a new family of solution-processable cyclometalated iridium(III) phosphors with carbazole (Cz) and/or diphenylphosphoryl (Ph2PO) units functionalized main ligands has been designed. Owing to Cz and Ph2PO moieties possessing bulky steric effects, they can suppress the intermolecular strong packing and then decrease TTA effects and emission quenching. Meanwhile, the resulting OLEDs based on the designed phosphors exhibit considerable efficiencies and relatively small efficiency roll-offs. The device based on 4 containing both Cz and Ph2PO units realized a maximum current efficiency of 21.3 cd A-1, accompanied by a small roll-off. By optimization of the configuration of OLEDs, the device performance can be further enhanced, demonstrating their potential for high-performance solution-processable PhOLEDs.
Design, synthesis and biological evaluation of novel 4-phenoxyquinoline derivatives containing 3-oxo-3,4-dihydroquinoxaline moiety as c-Met kinase inhibitors
Liu, Ju,Yang, Di,Yang, Xiuxiu,Nie, Minhua,Wu, Guodong,Wang, Zhunchao,Li, Wei,Liu, Yajing,Gong, Ping
, p. 4475 - 4486 (2017/07/22)
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.
A heterocyclic ligands containing compounds and methods for their preparation, application (by machine translation)
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Paragraph 0153-0157; 0158; 0159; 0160; 0161, (2016/10/08)
The present invention provides a compound containing heterocyclic ligands and its preparation method, an electroluminescent device. The present invention provides heterocycle-containing ligand compound, through the particular selection of heterocyclic ligands and different metal binding, can adjust the wavelength of the compound, the organic metal compound used in the organic electroluminescent device, to make the device light-emitting efficiency is improved, and the service life is long. (by machine translation)
Compound with heterocyclic ligand and preparation method and application thereof
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Paragraph 0106; 0107; 0108; 0109; 0110; 0111; 0112, (2016/10/08)
The invention provides a compound with a heterocyclic ligand and a preparation method and application thereof. According to the compound with the heterocyclic ligand, the specific heterocyclic ligand is selected to be combined with metal aluminum, so that after the obtained organic compound is applied to an organic light-emitting device, the light-emitting efficiency of the device is improved, and the service life is long.
Lithium compound with heterocyclic ligand and preparation method and application thereof
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Paragraph 0123; 0124; 0125; 0126; 0127, (2016/10/08)
The invention provides a lithium compound with a heterocyclic ligand and a preparation method and application thereof. According to the lithium compound with the heterocyclic ligand, the specific heterocyclic ligand is selected to be combined with metal lithium, so that after the obtained organic lithium compound is applied to an organic light-emitting device, the light-emitting efficiency of the device is improved, and the service life is long.
Synthesis and in silico evaluation of novel compounds for PET-based investigations of the norepinephrine transporter
Neudorfer, Catharina,Seddik, Amir,Shanab, Karem,Jurik, Andreas,Rami-Mark, Christina,Holzer, Wolfgang,Ecker, Gerhard,Mitterhauser, Markus,Wadsak, Wolfgang,Spreitzer, Helmut
, p. 1712 - 1730 (2015/01/30)
Since the norepinephrine transporter (NET) is involved in a variety of diseases, the investigation of underlying dysregulation-mechanisms of the norepinephrine (NE) system is of major interest. Based on the previously described highly potent and selective NET ligand 1-(3-(methylamino)-1-phenylpropyl)-3-phenyl-1,3-dihydro-2H-benzimidaz- ol-2-one (Me@APPI), this paper aims at the development of several fluorinated methylaminebased analogs of this compound. The newly synthesized compounds were computationally evaluated for their interactions with the monoamine transporters and represent reference compounds for PET-based investigation of the NET.
Square planar nickel(II) complexes with halogenated o- diiminobenzosemiquinonato ligation: Synthesis, characterization, and redox property
Zuo, Wansheng,Zhang, Long,Xie, Meihua,Deng, Liang
supporting information, p. 1473 - 1482 (2014/01/06)
Seven square planar bis(o-diiminobenzosemiquinonato)nickel(II) complexes, [Ni(o-C6H4(NH)(NAr))2] (Ar=Mes, 1; p-F-C 6H4, 2; p-Cl-C6H4, 3), [Ni(o-4,5-F2-C6H2(NH)(NPh))2] (4), and [Ni(o-4,5-Cl2-C6H2(NH)(NAr))2] (Ar=Ph, 5; 2,6-F2-C6H3, 6; 2,6-Cl 2-C6H3, 7), have been synthesized and characterized by 1H NMR, 13C NMR, 19F NMR, IR, UV-Vis-NIR, elemental analyses, HRMS, as well as single-crystal X-ray diffraction studies (1 and 7). The cyclic voltammograms of these complexes exhibit two reversible redox processes of [NiL2]0/1- and [NiL2]1-/2-, and one irreversible process of [NiL 2]0/2+. Substituent effects on the redox properties of these complexes, in addition with those of the known complexes [Ni(o-C 6H4(NH)(NPh))2] (8) and [Ni(o-3,5-Bu t2-C6H2(NH)2) 2] (9), are identified by comparing the half-wave potentials of the reduction waves, as 1≈92] parallels the electron-donating and -withdrawing ability of the substituent group. Reduction of 1 with one or two equivalents of sodium metal in THF has led to the isolation of [Na(THF) 3][1] and [Na(THF)3]2[1]. The structure data of these two complexes revealed by low-temperature X-ray crystallography suggest their corresponding electronic structures of [NiII(1L ·1-)(1L2-)]1- and [Ni II(1L2-)2]2-, which are in line with those of [9]n (n=1-, 2-) suggested by spectroelectrochemical study. Copyright
