2-(4-(2-fluoroethyl)phenyl)ethanol | 1115987-00-2

• 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: 2-(4-(2-fluoroethyl)phenyl)ethanol
• 英文别名: 2-[4-(2-Fluoroethyl)phenyl]ethanol；2-[4-(2-fluoroethyl)phenyl]ethanol
• CAS: 1115987-00-2
• 化学式: C₁₀H₁₃FO
• 分子量: 168.211
• InChiKey: KBNRFKKWTKSOIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-(2-fluoroethyl)phenyl)ethanol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到1-(2-bromoethyl)-4-(2-fluoroethyl)benzene
  参考文献：
  名称：

  New N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl phenylcarbamate analogs as σ2 receptor ligands: Synthesis, in vitro characterization, and evaluation as PET imaging and chemosensitization agents

  摘要：

  A series of N-substituted 9-azabicyclo[3.3.1] nonan-3 alpha-yl phenylcarbamate analogs were synthesized. Among them, WC-26 and WC-59 were identified as the most potent sigma(2) receptor ligands (K-i = 2.58 and 0.82 nM, respectively) with high selectivity against sigma(1) (K-i of sigma(1)/sigma(2) ratio = 557 and 2087, respectively). [F-18] WC-59 was radiolabeled via a nucleophilic substitution of a mesylate precursor by [F-18]fluoride and in vitro direct binding studies of [F-18]WC-59 were conducted using membrane preparations from murine EMT-6 solid breast tumors. The results indicate that [F-18]WC-59 binds specifically to sigma(2) receptors in vitro (K-d = similar to 2 nM). Biodistribution studies of [F-18]WC-59 in EMT-6 tumor-bearing mice indicated that the tracer was a less suitable candidate for clinical imaging studies than existing F-18 labeled sigma(2) receptor ligands. The ability of WC-26 to enhance the cytotoxic effects of the chemotherapy drug, doxorubicin, was evaluated in cell culture using the mouse breast tumor EMT-6 and the human tumor MDA-MB435. WC-26 greatly increased the ability of doxorubicin to kill these two tumor cell lines in vitro. These results indicate that WC-26 is potentially a useful chemosensitizer for the treatment of cancer when combined with conventional chemotherapeutics. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.025
• 作为产物：
  描述：

  2-(4-(2-fluoroethyl)phenyl)acetic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以78%的产率得到2-(4-(2-fluoroethyl)phenyl)ethanol
  参考文献：
  名称：

  New N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl phenylcarbamate analogs as σ2 receptor ligands: Synthesis, in vitro characterization, and evaluation as PET imaging and chemosensitization agents

  摘要：

  A series of N-substituted 9-azabicyclo[3.3.1] nonan-3 alpha-yl phenylcarbamate analogs were synthesized. Among them, WC-26 and WC-59 were identified as the most potent sigma(2) receptor ligands (K-i = 2.58 and 0.82 nM, respectively) with high selectivity against sigma(1) (K-i of sigma(1)/sigma(2) ratio = 557 and 2087, respectively). [F-18] WC-59 was radiolabeled via a nucleophilic substitution of a mesylate precursor by [F-18]fluoride and in vitro direct binding studies of [F-18]WC-59 were conducted using membrane preparations from murine EMT-6 solid breast tumors. The results indicate that [F-18]WC-59 binds specifically to sigma(2) receptors in vitro (K-d = similar to 2 nM). Biodistribution studies of [F-18]WC-59 in EMT-6 tumor-bearing mice indicated that the tracer was a less suitable candidate for clinical imaging studies than existing F-18 labeled sigma(2) receptor ligands. The ability of WC-26 to enhance the cytotoxic effects of the chemotherapy drug, doxorubicin, was evaluated in cell culture using the mouse breast tumor EMT-6 and the human tumor MDA-MB435. WC-26 greatly increased the ability of doxorubicin to kill these two tumor cell lines in vitro. These results indicate that WC-26 is potentially a useful chemosensitizer for the treatment of cancer when combined with conventional chemotherapeutics. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.025

文献信息

• New N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl phenylcarbamate analogs as σ2 receptor ligands: Synthesis, in vitro characterization, and evaluation as PET imaging and chemosensitization agents
  作者：Wenhua Chu、Jinbin Xu、Dong Zhou、Fanjie Zhang、Lynne A. Jones、Kenneth T. Wheeler、Robert H. Mach

  DOI：10.1016/j.bmc.2008.12.025

  日期：2009.2

  A series of N-substituted 9-azabicyclo[3.3.1] nonan-3 alpha-yl phenylcarbamate analogs were synthesized. Among them, WC-26 and WC-59 were identified as the most potent sigma(2) receptor ligands (K-i = 2.58 and 0.82 nM, respectively) with high selectivity against sigma(1) (K-i of sigma(1)/sigma(2) ratio = 557 and 2087, respectively). [F-18] WC-59 was radiolabeled via a nucleophilic substitution of a mesylate precursor by [F-18]fluoride and in vitro direct binding studies of [F-18]WC-59 were conducted using membrane preparations from murine EMT-6 solid breast tumors. The results indicate that [F-18]WC-59 binds specifically to sigma(2) receptors in vitro (K-d = similar to 2 nM). Biodistribution studies of [F-18]WC-59 in EMT-6 tumor-bearing mice indicated that the tracer was a less suitable candidate for clinical imaging studies than existing F-18 labeled sigma(2) receptor ligands. The ability of WC-26 to enhance the cytotoxic effects of the chemotherapy drug, doxorubicin, was evaluated in cell culture using the mouse breast tumor EMT-6 and the human tumor MDA-MB435. WC-26 greatly increased the ability of doxorubicin to kill these two tumor cell lines in vitro. These results indicate that WC-26 is potentially a useful chemosensitizer for the treatment of cancer when combined with conventional chemotherapeutics. (c) 2009 Elsevier Ltd. All rights reserved.