1-(3-Chloro-propyl)-5-methoxy-2-methyl-indole-3-carbaldehyde | 1200527-29-2

• 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: 1-(3-Chloro-propyl)-5-methoxy-2-methyl-indole-3-carbaldehyde
• 英文别名: 1-(3-Chloropropyl)-5-methoxy-2-methylindole-3-carbaldehyde；1-(3-chloropropyl)-5-methoxy-2-methylindole-3-carbaldehyde
• CAS: 1200527-29-2
• 化学式: C₁₄H₁₆ClNO₂
• 分子量: 265.74
• InChiKey: WXQKHLTVKHSGAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 1-(3-Chloro-propyl)-5-methoxy-2-methyl-indole-3-carbaldehyde 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 生成 (5-methoxy-2-methyl-1-(3-(4-methylpiperazin-1-yl)propyl)-1H-indol-3-yl)methanone
  参考文献：
  名称：

  Novel benzofuran-3-one indole inhibitors of PI3 kinase-α and the mammalian target of rapamycin: Hit to lead studies

  摘要：

  A series of benzofuran-3-one indole phosphatidylinositol-3-kinases (PI3K) inhibitors identified via HTS has been prepared. The optimized inhibitors possess single digit nanomolar activity against p110 alpha (PI3K-alpha), good pharmaceutical properties, selectivity versus p110 gamma (PI3K-gamma), and tunable selectivity versus the mammalian target of rapamycin ( mTOR). Modeling of compounds 9 and 32 in homology models of PI3K-alpha and mTOR supports the proposed rationale for selectivity. Compounds show activity in multiple cellular proliferation assays with signaling through the PI3K pathway confirmed via phospho-Akt inhibition in PC-3 cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.082
• 作为产物：
  描述：

  5-甲氧基-2-甲基-1H-吲哚-3-甲醛 、 1-溴-3-氯丙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(3-Chloro-propyl)-5-methoxy-2-methyl-indole-3-carbaldehyde
  参考文献：
  名称：

  Novel benzofuran-3-one indole inhibitors of PI3 kinase-α and the mammalian target of rapamycin: Hit to lead studies

  摘要：

  A series of benzofuran-3-one indole phosphatidylinositol-3-kinases (PI3K) inhibitors identified via HTS has been prepared. The optimized inhibitors possess single digit nanomolar activity against p110 alpha (PI3K-alpha), good pharmaceutical properties, selectivity versus p110 gamma (PI3K-gamma), and tunable selectivity versus the mammalian target of rapamycin ( mTOR). Modeling of compounds 9 and 32 in homology models of PI3K-alpha and mTOR supports the proposed rationale for selectivity. Compounds show activity in multiple cellular proliferation assays with signaling through the PI3K pathway confirmed via phospho-Akt inhibition in PC-3 cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.082

文献信息

• [EN] 3-SUBSTITUTED-1H-INDOLE, 3-SUBSTITUTED-1H-PYRROLO[2,3-B]PYRIDINE AND 3-SUBSTITUTED-1H-PYRROLO[3,2-B]PYRIDINE COMPOUNDS, THEIR USE AS MTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES<br/>[FR] COMPOSÉS 1H-INDOLE SUBSTITUÉ EN POSITION 3, 1H-PYRROLO[2,3-B]PYRIDINE SUBSTITUÉE EN POSITION 3 ET 1H-PYRROLO[3,2-B]PYRIDINE SUBSTITUÉE EN POSITION 3, LEUR UTILISATION COMME MTOR KINASE ET INHIBITEURS DE LA PI3 KINASE, ET LEURS SYNTHÈSES
  申请人：WYETH LLC

  公开号：WO2010030727A1

  公开（公告）日：2010-03-18

  The invention relates to 3-substituted-1H-indole, 3-substituted-1H-pyrrolo[2,3-b]pyridine, and 3-substituted-1H-pyrrolo[3,2-b]pyridine compounds of the Formula (I): or a pharmaceutically acceptable salt thereof, wherein the constituent variables are as defined herein, compositions comprising the compounds, and methods for making and using the compounds.

  这项发明涉及Formula (I)的3-取代-1H-吲哚、3-取代-1H-吡咯并[2,3-b]吡啶和3-取代-1H-吡咯并[3,2-b]吡啶化合物，或其药学上可接受的盐，其中组成变量如本文所定义，包括这些化合物的组合物，以及制备和使用这些化合物的方法。
• 3-SUBSTITUTED-1H-INDOLE COMPOUNDS, THEIR USE AS MTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES
  申请人：Bursavich Matthew Gregory

  公开号：US20090311217A1

  公开（公告）日：2009-12-17

  The invention relates to 3-substituted-1H-indole compounds of the Formula I: or a pharmaceutically acceptable salt thereof, wherein the constituent variables are as defined herein, compositions comprising the compounds, and methods for making and using the compounds.

  本发明涉及公式I的3-取代-1H-吲哚化合物或其药学上可接受的盐，其中组成变量如本文所定义，包括该化合物的组合物，以及制备和使用该化合物的方法。
• 3-SUBSTITUTED-1H-INDOLE, 3-SUBSTITUTED-1H-PYRROLO[2,3-B]PYRIDINE AND 3-SUBSTITUTED-1H-PYRROLO[3,2-B]PYRIDINE COMPOUNDS, THEIR USE AS MTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES
  申请人：Ayral-Kaloustian Semiramis

  公开号：US20100061982A1

  公开（公告）日：2010-03-11

  The invention relates to 3-substituted-1H-indole, 3-substituted-1H-pyrrolo[2,3-b]pyridine, and 3-substituted-1H-pyrrolo[3,2-b]pyridine compounds of the Formula 1: or a pharmaceutically acceptable salt thereof, wherein the constituent variables are as defined herein, compositions comprising the compounds, and methods for making and using the compounds.

  本发明涉及公式1中的3-取代-1H-吲哚、3-取代-1H-吡咯[2,3-b]吡啶和3-取代-1H-吡咯[3,2-b]吡啶化合物，或其药学上可接受的盐，其中组成变量如本文所定义，包括含有该化合物的组合物，以及制备和使用该化合物的方法。
• [EN] 3-SUBSTITUTED-1H-INDOLE COMPOUNDS, THEIR USE AS MTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES<br/>[FR] COMPOSÉS DE 1H-INDOLE 3 SUBSTITUÉS, LEUR UTILISATION EN TANT QU'INHIBITEURS DE 3MTOR KINASE ET P13 KINASE, ET LEURS SYNTHÈSES
  申请人：WYETH CORP

  公开号：WO2009155042A1

  公开（公告）日：2009-12-23

  The invention relates to 3-substituted-1 H-indole compounds of the Formula (I): or a pharmaceutically acceptable salt thereof, wherein the constituent variables are as defined herein, compositions comprising the compounds, and methods for making and using the compounds for the treatment of PI3 and mTOR kinase-mediated diseases, e.g. cancer.