5-(2-甲氧基乙氧基)-茚满-1-酮 | 28945-97-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 5-(2-甲氧基乙氧基)-茚满-1-酮
• 英文名称: 5-(2-methoxyethoxy)indan-1-one
• 英文别名: 5-(2-Methoxy-ethoxy)-1-indanon；5-(2-Methoxyethoxy)-2,3-dihydro-1H-inden-1-one；5-(2-methoxyethoxy)-2,3-dihydroinden-1-one
• CAS: 28945-97-3
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: CNIXRFXICOYMMC-UHFFFAOYSA-N

物化性质

• 沸点：
  351.5±42.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  Phenyl 5-(3-phenoxy-1-propynyl)-3-thiophenecarboxylate 、 5-(2-甲氧基乙氧基)-茚满-1-酮 在 sodium hydride 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  1,4-Dihydroindeno[1,2-c]pyrazoles with Acetylenic Side Chains as Novel and Potent Multitargeted Receptor Tyrosine Kinase Inhibitors with Low Affinity for the hERG Ion Channel

  摘要：

  The synthesis of a novel series of 1,4-dihydroindeno[1,2-c]pyrazoles with acetylene-type side chains is described. Optimization of those compounds as KDR kinase inhibitors identified 8, which displayed an oral activity in an estradiol-induced murine uterine edema model (ED50 = 3 mg/kg) superior to Sutent (ED50 = 9 mg/kg) and showed potent antitumor efficacy in an MX-1 human breast carcinoma xenograft tumor growth model (tumor growth inhibition = 90% at 25 mg/kg.day po). The compound was docked into a homology model of the homo-tetrameric pore domain of the hERG potassium channel to identify strategies to improve its cardiac safety profile. Systematic interruption of key binding interactions between 8 and Phe656, Tyr652, and Ser624 yielded 90, which only showed an IC50 of 11.6 mu M in the hERG patch clamp assay. The selectivity profile for 8 and 90 revealed that both compounds are multitargeted receptor tyrosine kinase inhibitors with low nanomolar potencies against the members of the VEGFR and PDGFR kinase subfamilies.

  DOI：

  10.1021/jm061223o
• 作为产物：
  描述：

  5-羟基-1-茚酮 、 2-氯乙基甲基醚 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以84%的产率得到5-(2-甲氧基乙氧基)-茚满-1-酮
  参考文献：
  名称：

  1,4-Dihydroindeno[1,2-c]pyrazoles with Acetylenic Side Chains as Novel and Potent Multitargeted Receptor Tyrosine Kinase Inhibitors with Low Affinity for the hERG Ion Channel

  摘要：

  The synthesis of a novel series of 1,4-dihydroindeno[1,2-c]pyrazoles with acetylene-type side chains is described. Optimization of those compounds as KDR kinase inhibitors identified 8, which displayed an oral activity in an estradiol-induced murine uterine edema model (ED50 = 3 mg/kg) superior to Sutent (ED50 = 9 mg/kg) and showed potent antitumor efficacy in an MX-1 human breast carcinoma xenograft tumor growth model (tumor growth inhibition = 90% at 25 mg/kg.day po). The compound was docked into a homology model of the homo-tetrameric pore domain of the hERG potassium channel to identify strategies to improve its cardiac safety profile. Systematic interruption of key binding interactions between 8 and Phe656, Tyr652, and Ser624 yielded 90, which only showed an IC50 of 11.6 mu M in the hERG patch clamp assay. The selectivity profile for 8 and 90 revealed that both compounds are multitargeted receptor tyrosine kinase inhibitors with low nanomolar potencies against the members of the VEGFR and PDGFR kinase subfamilies.

  DOI：

  10.1021/jm061223o

文献信息

• [EN] TRICYCLIC PYRAZOLE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES A BASE DE TYRAZOLES TRICYCLIQUES
  申请人：ABBOTT LAB

  公开号：WO2005095387A1

  公开（公告）日：2005-10-13

  Compounds of the present invention are useful for inhibiting protein tyrosine kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  本发明的化合物对抑制蛋白酪氨酸激酶具有用处。还公开了制备这些化合物的方法、含有这些化合物的组合物以及使用这些化合物进行治疗的方法。
• Chemotherapeutische Nitroheterocyclen, III. Darstellung von Nitrofurfuryliden-, Nitrothenyliden- und Nitropyrrolylmethylen-Verbindungen substituierter 1-Indanone und 1-Tetralone
  作者：Rudolf Albrecht、Eberhard Schröder

  DOI：10.1002/jlac.19707360112

  日期：1970.7.7

  Es werden Derivate des 1-Indanons und 1-Tetralons mit 5-Nitro-furfural, 5-Nitro-furfuraldiacetat, 5-Nitro-thiophen-2-aldehyd, 5-Nitro-thiophen-2-aldehyd-diacetat, 5-Nitro-pyrrol2-aldehyd oder N-Methyl-5-nitro-pyrrol-2-aldehyd kondensiert (8–66, Tab. 1). Bei durch H3PO4 bewirkten Kondensationen werden Acetylaminogruppen gleichzeitig hydrolysiert, bei in Acetanhydrid verlaufenden Kondensationen werden

  1-茚满酮和1-四氢萘酮与5-硝基糠醛，5-硝基糠醛二乙酸酯，5-硝基噻吩-2-醛，5-硝基噻吩-2-醛二乙酸酯，5-硝基吡咯有衍生物将-2-醛或N-甲基-5-硝基-吡咯-2-醛缩合（8-66，表1）。在由H 3 PO 4引起缩合的情况下，乙酰氨基同时水解，在乙酸酐发生缩合的情况下，同时进行OH基的乙酰化反应（78-83，表2）。 ）。描述了在苯核上取代的新的1-茚满酮和1-四氢萘酮衍生物。
• Tricyclic pyrazole kinase inhibitors
  申请人：Arnold D. Lee

  公开号：US20060014816A1

  公开（公告）日：2006-01-19

  Compounds of the present invention are useful for inhibiting protein tyrosine kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  本发明的化合物可用于抑制蛋白酪氨酸激酶。还公开了制备该化合物的方法，含有该化合物的组合物，以及使用该化合物的治疗方法。
• TRICYCLIC PYRAZOLE KINASE INHIBITORS
  申请人：ABBOTT LABORATORIES

  公开号：EP1740579A1

  公开（公告）日：2007-01-10
• US7468371B2
  申请人：——

  公开号：US7468371B2

  公开（公告）日：2008-12-23