3-(2-(pyrrolidin-1-yl)ethyl)phenol | 104126-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-(pyrrolidin-1-yl)ethyl)phenol
• 英文别名: 3-[2-(pyrrolidin-1-yl)ethyl]phenol；3-(2-pyrrolidin-1-ylethyl)phenol
• CAS: 104126-76-3
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: WAHJGWKYFSVYNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• 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-(pyrrolidin-1-yl)ethyl)phenol 、 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69.3%的产率得到5,6-Dimethoxy-2-(3-(2-(pyrrolidin-1-yl)ethyl)phenoxy)-indan-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-(pyrrolidin-1-yl)ethyl)phenol
  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

• Antiulcer benzimidazole derivatives
  申请人：The Boots Company PLC

  公开号：US04767769A1

  公开（公告）日：1988-08-30

  Compounds of formula I ##STR1## in which R.sub.1 and R.sub.2, which may be the same or different, are hydrogen, a C.sub.1 to C.sub.3 alkyl group or R.sub.1 and R.sub.2 together with the nitrogen to which they are attached form an optionally substituted heterocyclic ring; R.sub.3 and R.sub.4, which may be the same or different are hydrogen, a C.sub.1 to C.sub.3 alkyl or an optionally substituted C.sub.3 to C.sub.6 cycloalkyl group, or R.sub.3 and R.sub.4 together with the nitrogen to which they are attached form an optionally substituted heterocyclic ring; m is 0, 1 or 2; p is 0, 1 or 2; E is an alkylene group connected to or interrupted by an oxygen or a sulphur atom; J is hydrogen or a substituent group; and their pharmaceutically acceptable salts have utility as histamine H.sub.2 -receptor antagonists.

  化合物的结构式为I，其中R.sub.1和R.sub.2，可以相同也可以不同，是氢、C.sub.1到C.sub.3烷基或者R.sub.1和R.sub.2连同它们连接的氮原子形成一个可选择取代的杂环环；R.sub.3和R.sub.4，可以相同也可以不同，是氢、C.sub.1到C.sub.3烷基或者一个可选择取代的C.sub.3到C.sub.6环烷基，或者R.sub.3和R.sub.4连同它们连接的氮原子形成一个可选择取代的杂环环；m为0、1或2；p为0、1或2；E是连接到或被氧或硫原子中断的烷基基团；J是氢或取代基团；它们的药学上可接受的盐可用作组胺H.sub.2-受体拮抗剂。
• Therapeutic agents
  申请人：The Boots Company PLC

  公开号：EP0172631A1

  公开（公告）日：1986-02-26

  Compounds of formula in which R1 and R2, which may be the same or different, are hydrogen, a C1 to C3 alkyl group or R1 and R2 together with the nitrogen to which they are attached form an optionally substituted heterocyclic ring; R3 and R4, which may be the same or different are hydrogen, a C, to C3 alkyl or an optionally substituted C3 to C6 cycloalkyl group, or R3 and R4 together with the nitrogen to which they are attached form an optionally substituted heterocyclic ring; m is 0, 1 or 2; p is 0, 1 or 2; E is an alkylene group connected to or interrupted by an oxygen or a sulphur atom; J is hydrogen or a substituent group; and their pharmaceutically acceptable salts have utility as histamine H2-receptor antagonists.

  式化合物 其中 R1 和 R2（可以相同或不同）是氢、C1 至 C3 烷基或 R1 和 R2 与它们连接的氮一起形成任选取代的杂环；R3 和 R4（可以相同或不同）是氢、C, 至 C3 烷基或任选取代的 C3 至 C6 环烷基或 R3 和 R4 与它们连接的氮一起形成任选取代的杂环；m 是 0、1 或 2；p 是 0、1 或 2；E 是与氧原子或硫原子相连或被氧原子或硫原子打断的亚烷基；J 是氢或取代基；它们的药学上可接受的盐类具有组胺 H2 受体拮抗剂的作用。
• US4767769A
  申请人：——

  公开号：US4767769A

  公开（公告）日：1988-08-30
• US6214832B1
  申请人：——

  公开号：US6214832B1

  公开（公告）日：2001-04-10
• 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.