3-(2-氯乙氧基)苯胺 | 178910-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(2-氯乙氧基)苯胺
• 英文名称: 3-(2-chloroethoxy)aniline
• CAS: 178910-32-2
• 化学式: C₈H₁₀ClNO
• mdl: MFCD09971295
• 分子量: 171.626
• InChiKey: DXXPALPCLCHBSU-UHFFFAOYSA-N

物化性质

• 沸点：
  305.5±17.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  3-(2-氯乙氧基)苯胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 12.0h， 生成 7-methoxy-6-(3-morpholinopropoxy)-N-(3-(2-(2-nitro-1H-imidazol-1-yl)ethoxy)phenyl)quinazolin-4-amine
  参考文献：
  名称：

  <p>Design, synthesis, and biological study of 4-[(2-nitroimidazole-1<em>H</em>-alkyloxyl)aniline]-quinazolines as EGFR inhibitors exerting cytotoxicities both under normoxia and hypoxia</p>

  摘要：

  Purpose: In order to get novel EGFR inhibitors exerting more potency in tumor hypoxia than in normoxia.Methods: A series of 4-[(2-nitroimidazole-1H-alkyloxyl)aniline]-quinazolines were designed and synthesized, and their in vitro cytotoxicity and EGFR inhibitory activity were evaluated. Molecule docking study was performed for the representative compound.Results: The structure-activity relationship (SAR) studies revealed that compounds bearing both meta-chloride and para-(2-nitroimidazole-1H-alkyloxy) groups on the aniline displayed potent inhibitory activities both in enzymatic and cellular levels. The most promising compound 16i potently inhibited EGFR with an IC50 value of 0.12 mu M. Meanwhile, it manifested more potent cytotoxicity than the positive control lapatinib under tumor normoxia and hypoxia conditions (IC50 values of 1.59 and 1.09 mu M against A549 cells, 2.46 and 1.35 mu M against HT-29 cells, respectively). The proposed binding model of 16i in complex with EGFR was displayed by the docking results.Conclusion: This study provides insights for developing hypoxia-activated kinase inhibitors.

  DOI：

  10.2147/dddt.s209481
• 作为产物：
  描述：

  间硝基苯酚 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 3-(2-氯乙氧基)苯胺
  参考文献：
  名称：

  <p>Design, synthesis, and biological study of 4-[(2-nitroimidazole-1<em>H</em>-alkyloxyl)aniline]-quinazolines as EGFR inhibitors exerting cytotoxicities both under normoxia and hypoxia</p>

  摘要：

  Purpose: In order to get novel EGFR inhibitors exerting more potency in tumor hypoxia than in normoxia.Methods: A series of 4-[(2-nitroimidazole-1H-alkyloxyl)aniline]-quinazolines were designed and synthesized, and their in vitro cytotoxicity and EGFR inhibitory activity were evaluated. Molecule docking study was performed for the representative compound.Results: The structure-activity relationship (SAR) studies revealed that compounds bearing both meta-chloride and para-(2-nitroimidazole-1H-alkyloxy) groups on the aniline displayed potent inhibitory activities both in enzymatic and cellular levels. The most promising compound 16i potently inhibited EGFR with an IC50 value of 0.12 mu M. Meanwhile, it manifested more potent cytotoxicity than the positive control lapatinib under tumor normoxia and hypoxia conditions (IC50 values of 1.59 and 1.09 mu M against A549 cells, 2.46 and 1.35 mu M against HT-29 cells, respectively). The proposed binding model of 16i in complex with EGFR was displayed by the docking results.Conclusion: This study provides insights for developing hypoxia-activated kinase inhibitors.

  DOI：

  10.2147/dddt.s209481

文献信息

• Pyrrolo\x9b2,3-d!pyrimidines and their use
  申请人：Novartis Finance Corp.

  公开号：US05869485A1

  公开（公告）日：1999-02-09

  The invention relates to the use of the compounds mentioned below in the therapeutic treatment of tumor diseases and other proliferative diseases, such as psoriasis, and to novel compounds of that type. The compounds are compounds of formula I ##STR1## wherein n is from 0 to 5 and, when n is not 0, R is one or more substituents selected from halogen, alkyl, trifluoromethyl and alkoxy; and R.sub.1 and R.sub.2 are each independently of the other alkyl, or phenyl that is unsubstituted or substituted by halogen, trifluoromethyl, alkyl or by alkoxy, it also being possible for one of the two radicals R.sub.1 and R.sub.2 to be hydrogen, or R1 and R2 together form an alkylene chain having from 2 to 5 carbon atoms that is unsubstituted or substituted by alkyl; or salts thereof. Compounds of formula I inhibit protein kinases, for example the tyrosine protein kinase of the receptor for the epidermal growth factor, EGF.

  本发明涉及在治疗肿瘤疾病和其他增殖性疾病（例如银屑病）中使用下面提及的化合物，以及该类新颖化合物。这些化合物是公式I的化合物：##STR1##，其中n为0到5，当n不为0时，R为选自卤素、烷基、三氟甲基和烷氧基的一个或多个取代基；R.sub.1和R.sub.2各自独立地为烷基，或为未取代或被卤素、三氟甲基、烷基或烷氧基取代的苯基，两个自由基R.sub.1和R.sub.2中的一个也可以是氢，或者R1和R2共同形成一个有2到5个碳原子的未取代或被烷基取代的亚烷基链；或其盐。公式I的化合物可以抑制蛋白激酶，例如表皮生长因子（EGF）受体的酪氨酸蛋白激酶。
• 2-Pyrimidinyl Pyrazolopyridine ErbB Kinase Inhibitors
  申请人：Uehling David Edward

  公开号：US20090149456A1

  公开（公告）日：2009-06-11

  The present invention provides 2-pyrimidinyl pyrazolopyridine compounds, compositions containing the same, as well as processes for the preparation and their use as pharmaceutical agents.

  本发明提供了2-嘧啶基吡唑并吡啶化合物，含有该化合物的组合物，以及它们的制备方法和作为药物的应用。
• 2-Pyrimidinyl Pyrazolopyridine Erbb Kinase Inhibitors
  申请人：Uehling Edward David

  公开号：US20080051395A1

  公开（公告）日：2008-02-28

  The present invention provides 2-pyrimidinyl pyrazolopyridine compounds, compositions containing the same, as well as processes for the preparation and their use as pharmaceutical agents.

  本发明提供了2-嘧啶基吡唑吡啶化合物，含有这些化合物的组合物，以及其制备过程和作为药物剂的用途。
• 2-pyrimidinyl pyrazolopyridine ErbB kinase inhibitors
  申请人：GlaxoSmithKline LLC

  公开号：US07807673B2

  公开（公告）日：2010-10-05

  The present invention provides 2-pyrimidinyl pyrazolopyridine compounds, compositions containing the same, as well as processes for the preparation and their use as pharmaceutical agents.

  本发明提供了2-嘧啶基吡唑吡啶化合物，含有它们的组合物，以及制备它们的过程和它们作为药物的用途。
• New generation dopaminergic agents. 2. Discovery of 3-OH-phenoxyethylamine and 3-OH-N1-phenylpiperazine dopaminergic templates
  作者：Richard E. Mewshaw、Morris Husbands、Elizabeth S. Gildersleeve、Michael B. Webb、Xiaojie Shi、Hossein Mazandarani、Mark I. Cockett、Rafal Ochalski、Julie A. Brennan、Magid Abou-Gharbia、Karen Marquis、Georgia B. McGaughey、Joseph Coupet、Terrance H. Andree

  DOI：10.1016/s0960-894x(98)00014-6

  日期：1998.2

  Described in this report is a systematic study which led to the identification of two new dopamine D-2 partial agonists (5 and 17). Phenols 5 and 17 represent prototypes of two new classes of D-2 partial agonists as well as templates for the future design of novel dopaminergic agents. (C) 1998 Elsevier Science Ltd. All rights reserved.