208173-19-7Relevant academic research and scientific papers
2-chloro-3-fluoro-4-(trifluoromethyl) benzaldehyde and synthesis method thereof
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Paragraph 0018-0019; 0030-0031, (2021/04/10)
The invention belongs to the technical field of pesticide intermediates, and particularly relates to 2-chloro-3-fluoro-4-(trifluoromethyl) benzaldehyde. The invention discloses unreported 2-chloro-3-fluoro-4-(trifluoromethyl) benzaldehyde and a synthetic method thereof. In the synthesis process, the product is formed through reaction under normal pressure, the process is simple, industrial application is facilitated, reaction conditions are mild, operation is easy, and the industrial production requirement is met; the 2-chloro-3-fluoro-4-(trifluoromethyl) benzaldehyde disclosed by the invention can be widely applied to a pesticide synthesis process, such as synthesis of pesticides such as herbicides and the like, and is relatively high in synthesis yield and relatively high in purity.
A Dipolar Cycloaddition Reaction to Access 6-Methyl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridines Enables the Discovery Synthesis and Preclinical Profiling of a P2X7 Antagonist Clinical Candidate
Chrovian, Christa C.,Soyode-Johnson, Akinola,Peterson, Alexander A.,Gelin, Christine F.,Deng, Xiaohu,Dvorak, Curt A.,Carruthers, Nicholas I.,Lord, Brian,Fraser, Ian,Aluisio, Leah,Coe, Kevin J.,Scott, Brian,Koudriakova, Tatiana,Schoetens, Freddy,Sepassi, Kia,Gallacher, David J.,Bhattacharya, Anindya,Letavic, Michael A.
supporting information, p. 207 - 223 (2018/02/10)
A single pot dipolar cycloaddition reaction/Cope elimination sequence was developed to access novel 1,4,6,7-tetrahydro-5H-[1,2,3]triazolo[4,5-c]pyridine P2X7 antagonists that contain a synthetically challenging chiral center. The structure-activity relati
Novel quinazoline derivatives bearing various 6-benzamide moieties as highly selective and potent EGFR inhibitors
Hou, Weijie,Ren, Yan,Zhang, Zhenhua,Sun, Huan,Ma, Yongfen,Yan, Bo
, p. 1740 - 1750 (2018/03/12)
A series of novel quinazoline derivatives bearing various C-6 benzamide substituents were synthesized and evaluated as EGFR inhibitors, and most showed significant inhibitory potency against EGFR kinase. In particular, compound 6g possessed potent inhibitory activity against EGFR wild-type (IC50 = 5 nM), and strong antiproliferative activity against HCC827 and Ba/F3 (L858R) cell lines. Kinase profiling against a panel of 365 kinases showed that 6g was highly selective for EGFR. Furthermore, 6g showed desirable properties in assays of liver microsome metabolic stability and cytochromes P450 inhibition and preliminary pharmacokinetic study. The overall attractive profile of 6g made it an interesting compound for further development.
From Lead to Drug Candidate: Optimization of 3-(Phenylethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine Derivatives as Agents for the Treatment of Triple Negative Breast Cancer
Zhang, Chun-Hui,Chen, Kai,Jiao, Yan,Li, Lin-Li,Li, Ya-Ping,Zhang, Rong-Jie,Zheng, Ming-Wu,Zhong, Lei,Huang, Shen-Zhen,Song, Chun-Li,Lin, Wan-Ting,Yang, Jiao,Xiang, Rong,Peng, Bing,Han, Jun-Hong,Lu, Guang-Wen,Wei, Yu-Quan,Yang, Sheng-Yong
supporting information, p. 9788 - 9805 (2016/11/19)
Herein we report the sophisticated process of structural optimization toward a previously disclosed Src inhibitor, compound 1, which showed high potency in the treatment of triple negative breast cancer (TNBC) both in vitro and in vivo but had considerable toxicity. A series of 3-(phenylethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine derivatives were synthesized. In vitro cell-based phenotypic screening together with in vivo assays and structure-activity relationship (SAR) studies finally led to the discovery of N-(3-((4-amino-1-(trans-4-hydroxycyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)ethynyl)-4-methylphenyl)-4-methyl-3-(trifluoromethyl)benzamide (13an). 13an is a multikinase inhibitor, which potently inhibited Src (IC50 = 0.003 μM), KDR (IC50 = 0.032 μM), and several kinases involved in the MAPK signal transduction. This compound showed potent anti-TNBC activities both in vitro and in vivo, and good pharmacokinetic properties and low toxicity. Mechanisms of action of anti-TNBC were also investigated. Collectively, the data obtained in this study indicate that 13an could be a promising drug candidate for the treatment of TNBC and hence merits further studies.
P2X7 MODULATORS
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Paragraph 0403; 0404, (2014/09/30)
The present invention is directed to a compound of Formula (I) The invention also relates to pharmaceutical compositions comprising compounds of Formula (I). Methods of making and using the compounds of Formula (I) are also within the scope of the invention.
P2X7 MODULATORS
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Paragraph 0284; 0285, (2014/09/29)
The present invention is directed to compounds of Formulas (I, IIa and IIb): The invention also relates to pharmaceutical compositions comprising compounds of Formulas (I, IIa and IIb). Methods of making and using the compounds of Formulas (I, IIa and IIb) are also within the scope of the invention.
Biarylether amide quinolines as liver X receptor agonists
Bernotas, Ronald C.,Singhaus, Robert R.,Kaufman, David H.,Ullrich, John,Fletcher III, Horace,Quinet, Elaine,Nambi, Ponnal,Unwalla, Rayomand,Wilhelmsson, Anna,Goos-Nilsson, Annika,Farnegardh, Mathias,Wrobel, Jay
experimental part, p. 1663 - 1670 (2009/08/08)
A series of 4-(amido-biarylether)-quinolines was prepared as potential LXR agonists. Appropriate substitution with amide groups provided high affinity LXR ligands, some with excellent potency and efficacy in functional assays of LXR activity. Novel amide
Discovery and SAR of cinnolines/quinolines as liver X receptor (LXR) agonists with binding selectivity for LXRβ
Hu, Baihua,Unwalla, Raymound,Collini, Michael,Quinet, Elaine,Feingold, Irene,Goos-Nilsson, Annika,Wihelmsson, Anna,Nambi, Ponnal,Wrobel, Jay
experimental part, p. 3519 - 3527 (2009/10/17)
A series of cinnolines/quinolines was prepared and it was found that 4-phenyl-cinnoline/quinolines with either a 2′,3′ or 2′,5′-disubstituted benzyloxy moiety or the 1-Me-7-indole methoxy moiety on the meta position of the 4-phenyl ring showed good binding selectivity for LXRβ over LXRα. The LXRβ binding selective modulators displayed good activity for inducing ABCA1 gene expression in J774 macrophage cell line and poor efficacy in the LXRα Gal4 functional assay. 26, 37 and 41 were examined for their ability to induce SREBP-1c gene expression in Huh-7 liver cell line and they were weak partial agonists.
A strategy of employing aminoheterocycles as amide mimics to identify novel, potent and bioavailable soluble epoxide hydrolase inhibitors
Shen, Hong C.,Ding, Fa-Xiang,Deng, Qiaolin,Xu, Suoyu,Tong, Xinchun,Zhang, Xiaoping,Chen, Yuli,Zhou, Gaochao,Pai, Lee-Yuh,Alonso-Galicia, Magdalena,Roy, Sophie,Zhang, Bei,Tata, James R.,Berger, Joel P.,Colletti, Steven L.
experimental part, p. 5716 - 5721 (2010/04/30)
Distinct from previously reported urea and amide inhibitors of soluble epoxide hydrolase (sEH), a novel class of inhibitors were rationally designed based on the X-ray structure of this enzyme and known amide inhibitors. The structure-activity relationshi
Synthesis and structural characterization of new phosphinooxazoline complexes of iron
Sedinkin, Sergey L.,Rath, Nigam P.,Bauer, Eike B.
, p. 3081 - 3091 (2008/12/22)
The first phosphinooxazoline chelate complexes of iron were synthesized, and their structural and electronic properties were studied. The known phosphinooxazolines 2-(2-(diphenylphosphino)phenyl)-4,5-dihydrooxazole (7a), 2-(2-(diphenylphosphino)phenyl)-4,
