2-benzyl-4-((diethylamino)methyl)benzofuran-5-ol | 1580443-54-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-benzyl-4-((diethylamino)methyl)benzofuran-5-ol
• 英文别名: 2-Benzyl-4-(diethylaminomethyl)-1-benzofuran-5-ol；2-benzyl-4-(diethylaminomethyl)-1-benzofuran-5-ol
• CAS: 1580443-54-4
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: BMPZZXBPVILSIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  36.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (5-methoxybenzofuran-2-yl)(phenyl)methanone 在 三甲基氯硅烷 、 三溴化硼 、 sodium cyanoborohydride 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 76.0h， 生成 2-benzyl-4-((diethylamino)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

文献信息

• Synthesis of Functionalized Benzo[<i>b</i>]furans via Oxidative Cyclization of <i>o</i>-Cinnamyl Phenols
  作者：Mohammad Rehan、Rajender Nallagonda、Braja Gopal Das、Tannu Meena、Prasanta Ghorai

  DOI：10.1021/acs.joc.6b02752

  日期：2017.4.7

  Disclosed herein is an efficient synthetic route for the synthesis of functionalized 2-benzyl benzo[b]furans via a regioselective 5-exo-trig intramolecular oxidative cyclization of ortho-cinnamyl phenols using [PdCl2(CH3CN)2] as catalyst and benzoquinone as an oxidant. Further, a sequential ortho-cinnamylation of phenols using cinnamyl alcohols catalyzed by Re2O7, followed by an oxidative cyclization

  本文所公开的是用于官能化的2-苄基苯并[合成的有效合成路线b ]呋喃经由区域选择性5 -外-TRIG分子内的氧化环化邻-使用肉桂酚[的PdCl 2（CH 3 CN）2 ]作为催化剂和苯醌作为氧化剂。此外，使用由Re 2 O 7催化的肉桂醇对苯酚进行邻位邻肉桂酸化，然后使用上述Pd催化剂进行氧化环化。反应显示出广泛的底物范围，具有良好至优异的产率。
• 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.