3-(2-(二乙基氨基)乙基)苯酚 | 1009636-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(2-(二乙基氨基)乙基)苯酚
• 英文名称: 3-(2-(diethylamino)ethyl)phenol
• 英文别名: 3-[2-(diethylamino)ethyl]phenol
• CAS: 1009636-05-8
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: YYVUAQURLKVSID-UHFFFAOYSA-N

物化性质

• 沸点：
  304.7±25.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-(二乙基氨基)乙基)苯酚 、 2-溴-5,6-二甲氧基-1-茚酮 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以64%的产率得到2-(3-(2-(Diethylamino)ethyl)phenoxy)-5,6-dimethoxyindan-1-one
  参考文献：
  名称：

  2-Phenoxy-indan-1-one derivatives as acetylcholinesterase inhibitors: A study on the importance of modifications at the side chain on the activity

  摘要：

  As a part of our project aimed at developing new agents of potential application in AD, a new series of 2-phenoxy-indan-1-one derivatives which possess alkylamine side chain were designed, synthesized and evaluated for their inhibitory activity against AChE and BuChE. Most of the compounds were found to inhibit AChE in the nanomolar range. The optimum inhibitor 3g exhibited 34-fold increase in AChE inhibition than donepezil and displayed neuroprotective effect against H2O2-induced cell death. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.014
• 作为产物：
  描述：

  2-(3-羟基苯基)乙醇 在 四溴化碳 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 3-(2-(二乙基氨基)乙基)苯酚
  参考文献：
  名称：

  Non-Nucleoside Inhibitors of Human Adenosine Kinase: Synthesis, Molecular Modeling, and Biological Studies

  摘要：

  Adenosine kinase (AK) catalyzes the phosphorylation of adenosine (Ado) to AMP by means of a kinetic mechanism in which the two substrates Ado and ATP bind the enzyme in a binary and/or ternary complex, with distinct protein conformations. Most of the described inhibitors have Ado-like structural motifs and are nonselective; and some of them (e.g., the tubercidine-like ligands) are characterized by a toxic profile. We have cloned and expressed human AK (hAK) and searched for novel non-substrate-like inhibitors. Our efforts to widen the structural diversity of AK inhibitors led to the identification of novel non-nucleoside, noncompetitive allosteric modulators characterized by a unique molecular scaffold. Among the pyrrolobenzoxa(thia)zepinones (4a-qq) developed, 4a was identified as a non-nucleoside prototype hAK. inhibitor. 4a has proapoptotic efficacy, slight inhibition of short-term RNA synthesis, and cytostatic activity on tumor cell lines while showing low cytotoxicity and no significant adverse effects on short-term DNA synthesis in cells.

  DOI：

  10.1021/jm101438u

文献信息

• Non-Nucleoside Inhibitors of Human Adenosine Kinase: Synthesis, Molecular Modeling, and Biological Studies
  作者：Stefania Butini、Sandra Gemma、Margherita Brindisi、Giuseppe Borrelli、Andrea Lossani、Anna Maria Ponte、Andrea Torti、Giovanni Maga、Luciana Marinelli、Valeria La Pietra、Isabella Fiorini、Stefania Lamponi、Giuseppe Campiani、Daniela M. Zisterer、Seema-Maria Nathwani、Stefania Sartini、Concettina La Motta、Federico Da Settimo、Ettore Novellino、Federico Focher

  DOI：10.1021/jm101438u

  日期：2011.3.10

  Adenosine kinase (AK) catalyzes the phosphorylation of adenosine (Ado) to AMP by means of a kinetic mechanism in which the two substrates Ado and ATP bind the enzyme in a binary and/or ternary complex, with distinct protein conformations. Most of the described inhibitors have Ado-like structural motifs and are nonselective; and some of them (e.g., the tubercidine-like ligands) are characterized by a toxic profile. We have cloned and expressed human AK (hAK) and searched for novel non-substrate-like inhibitors. Our efforts to widen the structural diversity of AK inhibitors led to the identification of novel non-nucleoside, noncompetitive allosteric modulators characterized by a unique molecular scaffold. Among the pyrrolobenzoxa(thia)zepinones (4a-qq) developed, 4a was identified as a non-nucleoside prototype hAK. inhibitor. 4a has proapoptotic efficacy, slight inhibition of short-term RNA synthesis, and cytostatic activity on tumor cell lines while showing low cytotoxicity and no significant adverse effects on short-term DNA synthesis in cells.
• 2-Phenoxy-indan-1-one derivatives as acetylcholinesterase inhibitors: A study on the importance of modifications at the side chain on the activity
  作者：Yanhong Shen、Rong Sheng、Jing Zhang、Qiaojun He、Bo Yang、Yongzhou Hu

  DOI：10.1016/j.bmc.2008.07.014

  日期：2008.8

  As a part of our project aimed at developing new agents of potential application in AD, a new series of 2-phenoxy-indan-1-one derivatives which possess alkylamine side chain were designed, synthesized and evaluated for their inhibitory activity against AChE and BuChE. Most of the compounds were found to inhibit AChE in the nanomolar range. The optimum inhibitor 3g exhibited 34-fold increase in AChE inhibition than donepezil and displayed neuroprotective effect against H2O2-induced cell death. (C) 2008 Elsevier Ltd. All rights reserved.