6-chloro-3-[(4-methoxyphenyl)methylidene]-1H-indol-2-one | 387344-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-chloro-3-[(4-methoxyphenyl)methylidene]-1H-indol-2-one
• CAS: 387344-13-0
• 化学式: C₁₆H₁₂ClNO₂
• 分子量: 285.73
• InChiKey: QDKZNLNLCWQQDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-3-[(4-methoxyphenyl)methylidene]-1H-indol-2-one 、 ALPHA-氯-4-甲氧基苯甲醛肟 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 26.0h， 以107 mg的产率得到6-chloro-3',4'-bis(4-methoxyphenyl)spiro[indoline-3,5'-isoxazoline]-2-one
  参考文献：
  名称：

  Synthesis and evaluation of spiroisoxazoline oxindoles as anticancer agents

  摘要：

  Restoring p53 levels through disruption of p53-MDM2 interaction has been proved to be a valuable approach in fighting cancer. We herein report the synthesis and evaluation of eighteen spiroisoxazoline oxindoles derivatives as p53-MDM2 interaction inhibitors. Seven compounds showed an antiproliferative profile superior to the p53-MDM2 interaction inhibitor nutlin-3, and induced cell death by apoptosis. Moreover, proof-of-concept was demonstrated by inhibition of the interaction between p53 and MDM2 in a live-cell bimolecular fluorescence complementation assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.048
• 作为产物：
  描述：

  6-氯氧化吲哚 、 4-甲氧基苯甲醛 在 哌啶 作用下， 生成 6-chloro-3-[(4-methoxyphenyl)methylidene]-1H-indol-2-one
  参考文献：
  名称：

  Synthesis of novel spiropyrazoline oxindoles and evaluation of cytotoxicity in cancer cell lines

  摘要：

  A series of novel spiropyrazoline oxindole derivatives was synthesized by 1,3-dipolar cycloaddition reaction. The compounds were screened for their in vitro cytotoxic activity against MCF-7 breast cancer cell line (estrogen receptor positive (ER+) and human epidermal growth factor receptor 2 negative (HER2-)). Of the nineteen spiropyrazoline oxindoles tested, six compounds have a GI(50) below 12 mu M The most potent compounds in this series were also evaluated against MDA-MB-231 breast cancer cell line (ER and HER2-). Two spiropyrazoline oxindoles were highly selective between MCF-7 tumor cells and MDA-MB-231 tumor cells. More importantly, they were noncytotoxic against HER 293T non tumor derived cell lines. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.023

文献信息

• BENZYLIDENE-INDOLINONE COMPOUNDS AND THEIR MEDICAL USE
  申请人：GO Mei Lin

  公开号：US20130035364A1

  公开（公告）日：2013-02-07

  Compounds of general formula I: wherein R 1a , R 1b , R 2 , R 3a , R 3b and X are as defined herein are tyrosine kinase inhibitors and are useful for the treatment of various diseases and conditions, for example cancer.

  通式I的化合物： 其中 R 1a ，R 1b ，R 2 ，R 3a ，R 3b 和X如本文所定义的那样是酪氨酸激酶抑制剂，对于治疗各种疾病和病况，例如癌症，是有用的。
• [EN] NOVEL BENZYLIDENE-INDOLINONE AND THEIR MEDICAL AND DIAGNOSTIC USES<br/>[FR] NOUVEAUX BENZYLIDÈNE-INDOLINONES ET LEURS UTILISATIONS MÉDICALE ET EN DIAGNOSTIC
  申请人：UNIV SINGAPORE

  公开号：WO2010044753A1

  公开（公告）日：2010-04-22

  The present invention relates generally to organic chemistry, biochemistry, pharmacology and medicine. More particularly, it relates to 3-benzylidene-indolin-2-one derivatives and their physiologically acceptable salts and prodrugs which modulate the activity of protein kinases ("PKs"), especially protein tyrosine kinase, and, therefore, are expected to exhibit a salutary effect against disorders related to abnormal PK activity. The present invention is further directed to methods of using of these compounds, alone or in combination with other therapeutic agents, for the alleviation, prevention and/or treatment of protein kinase-mediated diseases and disorders, such as cancer.

  本发明通常涉及有机化学、生物化学、药理学和医学。更具体地，涉及到3-苄基亚甲基吲哚啉-2-酮衍生物及其生理上可接受的盐和前药，其调节蛋白激酶（“PKs”）的活性，特别是蛋白酪氨酸激酶，因此预计对与异常PK活性相关的疾病表现出有益效果。本发明进一步涉及使用这些化合物的方法，单独或与其他治疗剂联合使用，用于缓解、预防和/或治疗蛋白激酶介导的疾病和疾病，如癌症。
• Small molecule inhibitors of MDM2 and the uses thereof
  申请人：Wang Shaomeng

  公开号：US20060211757A1

  公开（公告）日：2006-09-21

  The invention relates to small molecules which function as inhibitors of the interaction between p53 and MDM2. The invention also relates to the use of these compounds for inhibiting cell growth, inducing cell death, inducing cell cycle arrest and/or sensitizing cells to additional agent(s).

  这项发明涉及小分子，其作为p53和MDM2之间相互作用的抑制剂。该发明还涉及使用这些化合物来抑制细胞生长、诱导细胞死亡、诱导细胞周期停滞和/或使细胞对其他药物敏感。
• SMALL MOLECULE INHIBITORS OF MDM2 AND THE USES THEREOF
  申请人：Wang Shaomeng

  公开号：US20120101092A1

  公开（公告）日：2012-04-26

  The invention relates to small molecules which function as inhibitors of the interaction between p53 and MDM2. The invention also relates to the use of these compounds for inhibiting cell growth, inducing cell death, inducing cell cycle arrest and/or sensitizing cells to additional agent(s).

  本发明涉及小分子，其作为p53和MDM2相互作用的抑制剂。本发明还涉及使用这些化合物来抑制细胞生长，诱导细胞死亡，诱导细胞周期停滞和/或使细胞对其他药物更敏感。
• PROCESS FOR THE PREPARATION OF SMALL MOLECULE INHIBITORS OF MDM2 AND INTERMEDIATES USED THEREIN
  申请人：Wang Shaomeng

  公开号：US20130030173A1

  公开（公告）日：2013-01-31

  The invention relates to small molecules which function as inhibitors of the interaction between p53 and MDM2. The invention also relates to the use of these compounds for inhibiting cell growth, inducing cell death, inducing cell cycle arrest and/or sensitizing cells to additional agent(s).

  本发明涉及作为p53和MDM2相互作用抑制剂的小分子。本发明还涉及使用这些化合物来抑制细胞生长，诱导细胞死亡，诱导细胞周期阻滞和/或使细胞对其他药物敏感。