4-氟-N1,N1-二甲基-1,3-苯二胺 | 192819-46-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-氟-N1,N1-二甲基-1,3-苯二胺
• 中文别名: 1,3-苯二胺,4-氟-N1,N1-二甲基-(9CI)
• 英文名称: 4-fluoro-N1,N1-dimethylbenzene-1,3-diamine
• 英文别名: 4-fluoro-N',N'-dimethyl-benzene-1,3-diamine；4-fluoro-1-N,1-N-dimethylbenzene-1,3-diamine
• CAS: 192819-46-8
• 化学式: C₈H₁₁FN₂
• 分子量: 154.187
• InChiKey: QJCJGFWDPGXSAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氟-N1,N1-二甲基-1,3-苯二胺 在 吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 82.0h， 生成 1-(5-bromopyridin-2-yl)-3-(2-fluoro-5-trifluoromethylphenyl)urea
  参考文献：
  名称：

  Substituted Indoles, Compositions Containing Them, Method for the Production Thereof and Their Use

  摘要：

  式(I)的化合物：其中R1、R5、R6、R7、Ar、L、A和Q如描述中所定义，并其盐，含有它们的组合物，制备它们的方法，以及它们作为药物的用途，特别是作为抗癌剂。

  公开号：

  US20070259910A1
• 作为产物：
  描述：

  4-氟-N,N-二甲基-3-硝基苯胺 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 4-氟-N1,N1-二甲基-1,3-苯二胺
  参考文献：
  名称：

  分子内氢键对开关异构化的取代基影响

  摘要：

  在这项工作中，揭示了一种基开关中取代基对氢键的影响。使用NMR技术评估这些的E / Z异构化比例及其在Z形式下的分子内氢键强度。还探讨了这些参数与Hammett经验值之间关于取代基效应的线性相关性。

  DOI：

  10.1016/j.tet.2019.06.022

文献信息

• N‐Heterocyclic Carbene Catalyzed Concerted Nucleophilic Aromatic Substitution of Aryl Fluorides Bearing α,β‐Unsaturated Amides
  作者：Kosuke Yasui、Miharu Kamitani、Mamoru Tobisu

  DOI：10.1002/anie.201907837

  日期：2019.10

  N-heterocyclic carbene (NHC)-catalyzed intramolecular cyclization of acrylamides that contain a 2-fluorophenyl group on the nitrogen through a CSN Ar reaction. By using this catalytic method, it is possible to synthesize an array of quinolin-2-one derivatives, which are common structural motifs in pharmaceuticals and organic materials. DFT calculations unambiguously revealed that this reaction proceeds through

  协同的亲核芳族取代（CSN Ar）已经成为一种强大的机械流形，其中亲核芳族取代可以一步进行，而无需形成迈森海默中间体。然而，迄今为止报道的所有CSN Ar反应均需要化学计量的强碱或活化剂，并且尚未报道催化变体。在本文中，我们报告了通过CSN Ar反应，N杂环卡宾（NHC）催化的在氮原子上包含2-氟苯基的丙烯酰胺的分子内环化反应。通过使用这种催化方法，可以合成一系列喹啉-2-酮衍生物，它们是药物和有机材料中常见的结构基序。
• [EN] SUBSTITUTED 1,6-NAPHTHYRIDINE INHIBITORS OF CDK5<br/>[FR] INHIBITEURS DE CDK5 DE TYPE 1,6-NAPHTYRIDINE SUBSTITUÉE
  申请人：GOLDFINCH BIO INC

  公开号：WO2022011274A1

  公开（公告）日：2022-01-13

  Disclosed are compounds having structural formula I, and related salts and pharmaceutical compositions. Also disclosed are therapeutic methods, e.g., of treating diseases and conditions such as kidney disease, kidney failure, kidney stones, or polycystic kidney disease, using the compounds of formula (I), and related salts and pharmaceutical compositions.

  揭示了具有结构式I的化合物，以及相关的盐和药物组合物。还揭示了治疗方法，例如利用结构式(I)的化合物、相关盐和药物组合物治疗疾病和病况，如肾病、肾衰竭、肾结石或多囊肾病。
• Substituted indoles, compositions containing them, method for the production thereof and their use
  申请人：Aventis Pharma S.A.

  公开号：US07566736B2

  公开（公告）日：2009-07-28

  Compounds of formula (I): wherein R1, R5, R6, R7, Ar, L, A, and Q are as defined in the description, and to salts thereof, to compositions containing them, to the process for preparing them, and to their use as medicinal products, in particular as anticancer agents.

  式(I)的化合物：其中R1、R5、R6、R7、Ar、L、A和Q如描述中所定义，以及其盐、含有它们的组合物、制备它们的方法以及它们作为药物特别是抗癌剂的用途。
• Discovery of <i>N</i>-((4-([1,2,4]Triazolo[1,5-<i>a</i>]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1<i>H</i>-imidazol-2-yl)methyl)-2-fluoroaniline (EW-7197): A Highly Potent, Selective, and Orally Bioavailable Inhibitor of TGF-β Type I Receptor Kinase as Cancer Immunotherapeutic/Antifibrotic Agent
  作者：Cheng Hua Jin、Maddeboina Krishnaiah、Domalapally Sreenu、Vura B. Subrahmanyam、Kota S. Rao、Hwa Jeong Lee、So-Jung Park、Hyun-Ju Park、Kiho Lee、Yhun Yhong Sheen、Dae-Kee Kim

  DOI：10.1021/jm500115w

  日期：2014.5.22

  A series of 2-substituted-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyriclin-2-yl)imidazoles was synthesized and evaluated to optimize a prototype inhibitor of TGF-beta type I receptor kinase (ALK5), 6. Combination of replacement of a quinoxalin-6-yl moiety of 6 with a [1,2,4]triazolo[1,5-a]pyridin-6-yl moiety, insertion of a methyleneamino linker, and a o-F substituent in the phenyl ring markedly increased ALK5 inhibitory activity, kinase selectivity, and oral bioavailability. The 12b (EW-7197) inhibited ALKS with IC50 value of 0.013 mu M in a kinase assay and with IC50 values of 0.0165 and 0.0121 mu M in HaCaT (3TP-luc) stable cells and 4T1 (3TP-luc) stable cells, respectively, in a luciferase assay. Selectivity profiling of 12b using a panel of 320 protein kinases revealed that it is a highly selective ALKS/ALK4 inhibitor. Pharmacokinetic study with 12b center dot HCl in rats showed an oral bioavailability of 51% with high systemic exposure (AUC) of 1426 ng x h/mL and maximum plasma concentration (C-max) of 1620 ng/mL. Rational optimization of 6 has led to the identification of a highly potent, selective, and orally bioavailable ALK5 inhibitor 12b.
• 4-([1,2,4]Triazolo[1,5-a]pyridin-6-yl)-5(3)-(6-methylpyridin-2-yl)imidazole and -pyrazole derivatives as potent and selective inhibitors of transforming growth factor-β type I receptor kinase
  作者：Cheng Hua Jin、Maddeboina Krishnaiah、Domalapally Sreenu、Vura Bala Subrahmanyam、Hyun-Ju Park、So-Jung Park、Yhun Yhong Sheen、Dae-Kee Kim

  DOI：10.1016/j.bmc.2014.03.022

  日期：2014.5

  A series of 4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5(3)-(6-methylpyridin-2-yl)imidazoles and -pyrazoles 14a-c, 15a-c, 16a, 16b, 19a-d, 21a, and 21b has been synthesized and evaluated for their ALK5 inhibitory activity in an enzyme assay and in a cell-based luciferase reporter assay. Among them, the pyrazole derivative 21b inhibited ALK5 phosphorylation with an IC50 value of 0.018 mu M and showed 95% inhibition at 0.03 mu M in a luciferase reporter assay using HaCaT cells permanently transfected with p3TP-luc reporter construct. The 21b showed a high selectivity index of 284 against p38 alpha MAP kinase. The binding pose of 21b generated by docking analysis reveals that it fits well into the ATP binding cavity of ALK5 by forming several hydrogen bond interactions. (C) 2014 Elsevier Ltd. All rights reserved.