(4-((1,4'-bipiperidin)-1'-ylmethyl)-5-hydroxybenzofuran-2-yl)(phenyl)methanone | 1580443-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-((1,4'-bipiperidin)-1'-ylmethyl)-5-hydroxybenzofuran-2-yl)(phenyl)methanone
• 英文别名: [5-Hydroxy-4-[(4-piperidin-1-ylpiperidin-1-yl)methyl]-1-benzofuran-2-yl]-phenylmethanone；[5-hydroxy-4-[(4-piperidin-1-ylpiperidin-1-yl)methyl]-1-benzofuran-2-yl]-phenylmethanone
• CAS: 1580443-49-7
• 化学式: C₂₆H₃₀N₂O₃
• 分子量: 418.536
• InChiKey: JHCVIKZBDUECSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  56.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-((1,4'-bipiperidin)-1'-ylmethyl)-5-hydroxybenzofuran-2-yl)(phenyl)methanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以90%的产率得到4-((1,4'-bipiperidin)-1'-ylmethyl)-2-(hydroxy(phenyl)methyl)benzofuran-5-ol
  参考文献：
  名称：

  Benzofuran derivatives as a novel class of inhibitors of mTOR signaling

  摘要：

  High-throughput screening (HTS) hit 1 was previously identified as an inhibitor of the Akt/mTOR (Akt/mammalian target of rapamycin) signaling, which is a major target in oncology. The cytotoxicity of 1 was determined on a panel of human cancer cells lines with an IC50 comprised between 30 and 140 mu M. Subsequent structure activity relationship (SAR) studies led us to the identification of compounds that displayed an enhanced cytotoxicity. We demonstrated also that these molecules directly bind to mTOR complex 1 (mTORC1) and inhibit its kinase activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.020
• 作为产物：
  描述：

  (5-methoxybenzofuran-2-yl)(phenyl)methanone 在 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 (4-((1,4'-bipiperidin)-1'-ylmethyl)-5-hydroxybenzofuran-2-yl)(phenyl)methanone
  参考文献：
  名称：

  Benzofuran derivatives as a novel class of inhibitors of mTOR signaling

  摘要：

  High-throughput screening (HTS) hit 1 was previously identified as an inhibitor of the Akt/mTOR (Akt/mammalian target of rapamycin) signaling, which is a major target in oncology. The cytotoxicity of 1 was determined on a panel of human cancer cells lines with an IC50 comprised between 30 and 140 mu M. Subsequent structure activity relationship (SAR) studies led us to the identification of compounds that displayed an enhanced cytotoxicity. We demonstrated also that these molecules directly bind to mTOR complex 1 (mTORC1) and inhibit its kinase activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.020

文献信息

• Benzofuran derivatives as a novel class of inhibitors of mTOR signaling
  作者：Christophe Salomé、Vanessa Narbonne、Nigel Ribeiro、Frédéric Thuaud、Maria Serova、Armand de Gramont、Sandrine Faivre、Eric Raymond、Laurent Désaubry

  DOI：10.1016/j.ejmech.2013.12.020

  日期：2014.3

  High-throughput screening (HTS) hit 1 was previously identified as an inhibitor of the Akt/mTOR (Akt/mammalian target of rapamycin) signaling, which is a major target in oncology. The cytotoxicity of 1 was determined on a panel of human cancer cells lines with an IC50 comprised between 30 and 140 mu M. Subsequent structure activity relationship (SAR) studies led us to the identification of compounds that displayed an enhanced cytotoxicity. We demonstrated also that these molecules directly bind to mTOR complex 1 (mTORC1) and inhibit its kinase activity. (C) 2013 Elsevier Masson SAS. All rights reserved.