N-(20-azido-3,6,9,12,15,18-hexaoxaicosyl)-1'-((5-hydroxy-2-phenylbenzofuran-4-yl)methyl)(1,4'-bipiperidine)-4-carboxamide | 1580443-52-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: N-(20-azido-3,6,9,12,15,18-hexaoxaicosyl)-1'-((5-hydroxy-2-phenylbenzofuran-4-yl)methyl)(1,4'-bipiperidine)-4-carboxamide
• CAS: 1580443-52-2
• 化学式: C₄₀H₅₈N₆O₉
• 分子量: 766.935
• InChiKey: ATJCPCLTBJBQJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  55.0
• 可旋转键数：
  26.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  173.09
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-(20-azido-3,6,9,12,15,18-hexaoxaicosyl)-1'-((5-hydroxy-2-phenylbenzofuran-4-yl)methyl)(1,4'-bipiperidine)-4-carboxamide 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 16.0h， 以100%的产率得到N-(20-amino-3,6,9,12,15,18-hexaoxaicosyl)-1′-((5-hydroxy-2-phenylbenzofuran-4-yl)methyl)-(1,4′-bipiperidine)-4-carboxamide
  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：

  2-phenylbenzofuran-5-ol 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 16.25h， 生成 N-(20-azido-3,6,9,12,15,18-hexaoxaicosyl)-1'-((5-hydroxy-2-phenylbenzofuran-4-yl)methyl)(1,4'-bipiperidine)-4-carboxamide
  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