2-(2-氟乙氧基)-5-碘苯甲酸 | 193882-73-4

• 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: 2-(2-氟乙氧基)-5-碘苯甲酸
• 英文名称: 2-(2-fluoroethoxy)-5-iodobenzoic acid
• CAS: 193882-73-4
• 化学式: C₉H₈FIO₃
• 分子量: 310.064
• InChiKey: PJPPFIGQECKBEH-UHFFFAOYSA-N

物化性质

• 熔点：
  129-130 °C(Solv: ethanol (64-17-5))
• 沸点：
  389.6±42.0 °C(Predicted)
• 密度：
  1.823±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-氟乙氧基)-5-碘苯甲酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 5-iodo-2-(2-fluoroethoxy)benzoyl chloride
  参考文献：
  名称：

  Synthesis and 5-HT-3 receptor binding activity of 5-[125I]iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide and its 5-halogen-2-alkoxyl homologues

  摘要：

  (S)-5-Iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (MIZAC) was prepared from 5-iodo-2,3-dimethoxybenzoyl chloride and (S)-3-aminoquinuclidine. [I-125]Iodode-stannylation of its corresponding 5-tri-n-butyltin derivative gave [I-125]-MIZAC at 1800 Ci/mmol. Binding of [I-125]-MIZAC in rat entorhinal cortex revealed a K-D of 1.37 +/- 0.21 nM. A series of racemic 2-O-alkyl derivatives of MIZAC were prepared and 5-HT-3 receptor affinities were determined by inhibition of [I-125]-MIZAC binding. Optimal affinity for the receptor was obtained with small, electron-withdrawing substituents in the aromatic 5-position and with bulky substituents in the 3-position. [I-125]-MIZAC is a selective radioligand useful for in vitro identification of the 5-HT-3 receptor.

  DOI：

  10.1016/s0223-5234(97)81676-5
• 作为产物：
  描述：

  5-碘水杨酸 在 硫酸 、 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 2-(2-氟乙氧基)-5-碘苯甲酸
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Fluorine-Containing D₃ Dopamine Receptor Ligands

  摘要：

  A series of fluorine-containing N-(2-methoxyphenyl)piperazine and N-(2-fluoroethoxy)piperazine analogues were synthesized, and their affinities for human dopamine D-2, D-3, and D-4 receptors were determined. Radioligand binding studies identified five compounds, 18a, 20a, 20c, 20e, and 21e, which bind with high affinity at D-3 (K-i = 0.17-5 nM) and moderate to high selectivity for D-3 VS D-2 receptors (ranging from similar to 25-to 163-fold). These compounds were also evaluated for intrinsic activity at D-2 and D3 receptors using a forskolin-dependent adenylyl cyclase assay. This panel of compounds exhibits varying receptor subtype binding selectivity and intrinsic activity at D-2 VS D-3 receptors. These compounds may be useful for behavioral pharmacology studies on the role of D-2-like dopamine receptors in neuropsychiatric and neurological disorders. Furthermore, compound 20e, which has the highest binding affinity and selectivity for the D-3 receptor (K-i = 0.17 nM for D-3, 163-fold selectivity for D-3 VS D-2 receptors), represents a candidate fluorine-18 radiotracer for in vivo PET imaging studies on the regulation of D-3 receptor expression.

  DOI：

  10.1021/jm101323b

文献信息

• Precursor synthesis and radiolabelling of [11C]ADAM: a potential radioligand for the serotonin transporter exploration by PET
  作者：Johnny VERCOUILLIE、Jari TARKIAINEN、Christer HALLDIN、Patrick EMOND、Sylvie CHALON、Johan SANDELL、Oliver LANGER、Denis GUILLOTEAU

  DOI：10.1002/jlcr.436

  日期：2001.2

  The serotoninergic system is involved in a variety of neurological and psychiatric disorders. Exploration of the serotonin transporters (5-HTT) in living human brain by PET would be of great value for better understanding, diagnosis and therapeutic follow up of these diseases. In order to obtain a selective radioligand to explore the 5-HTT by PET we report the synthesis of [11C]N,N-dimethyl-2-(2-amino-4-iodophenylthio)-benzylamine ([11C]ADAM). The precursor for labelling N-demethyl ADAM, was obtained in five steps using 2,5-dibromonitrobenzene and 2-thio-N-methylbenzamide as starting material. [11C]ADAM was synthesised by N-alkylation of the precursor using [11C]methyl iodide in DMF. The incorporation yield of [11C]methyl iodide was in the range of 50 to 70%. Finally [11C]ADAM was obtained in 30 minutes synthesis time including HPLC and with a radiochemical purity better than 99%. Copyright © 2001 John Wiley & Sons, Ltd.

  血清素能系统与多种神经和精神疾病有关。利用正电子发射计算机断层显像技术研究活体人脑中的血清素转运体（5-HTT）对更好地了解、诊断和跟踪治疗这些疾病具有重要价值。为了获得通过 PET 研究 5-HTT 的选择性放射性配体，我们报告了[11C]N,N-二甲基-2-（2-氨基-4-碘苯硫基）-苄胺（[11C]ADAM）的合成。标记 N-二甲基 ADAM 的前体以 2,5-二溴硝基苯和 2-硫代-N-甲基苯甲酰胺为起始原料，分五步获得。在 DMF 中使用[11C]甲基碘对前体进行 N-烷基化合成了[11C]ADAM。[11C]甲基碘的结合率在 50% 到 70% 之间。最后，[11C]ADAM 在包括 HPLC 在内的 30 分钟合成时间内获得，放射化学纯度优于 99%。Copyright © 2001 John Wiley & Sons, Ltd. All Rights Reserved.
• Synthesis and Structure–Activity Relationship Studies of Conformationally Flexible Tetrahydroisoquinolinyl Triazole Carboxamide and Triazole Substituted Benzamide Analogues as σ₂ Receptor Ligands
  作者：Suping Bai、Shihong Li、Jinbin Xu、Xin Peng、Kiran Sai、Wenhua Chu、Zhude Tu、Chenbo Zeng、Robert H. Mach

  DOI：10.1021/jm5001453

  日期：2014.5.22

  Two novel classes of compounds targeting the sigma-2 (sigma(2)) receptor were synthesized, and their bioactivities to binding sigma(1) and sigma(2) receptors were measured. Four novel triazole carboxamide analogues, 24d, 24e, 24f, and 39c, demonstrated high affinity and selectivity for the sigma(2) receptor. These data suggest C-11-labeled versions of these compounds may be potential sigma(2)-selective radiotracers for imaging the proliferative status of solid tumors.
• Synthesis and Pharmacological Evaluation of Fluorine-Containing D₃ Dopamine Receptor Ligands
  作者：Zhude Tu、Shihong Li、Jinquan Cui、Jinbin Xu、Michelle Taylor、David Ho、Robert R. Luedtke、Robert H. Mach

  DOI：10.1021/jm101323b

  日期：2011.3.24

  A series of fluorine-containing N-(2-methoxyphenyl)piperazine and N-(2-fluoroethoxy)piperazine analogues were synthesized, and their affinities for human dopamine D-2, D-3, and D-4 receptors were determined. Radioligand binding studies identified five compounds, 18a, 20a, 20c, 20e, and 21e, which bind with high affinity at D-3 (K-i = 0.17-5 nM) and moderate to high selectivity for D-3 VS D-2 receptors (ranging from similar to 25-to 163-fold). These compounds were also evaluated for intrinsic activity at D-2 and D3 receptors using a forskolin-dependent adenylyl cyclase assay. This panel of compounds exhibits varying receptor subtype binding selectivity and intrinsic activity at D-2 VS D-3 receptors. These compounds may be useful for behavioral pharmacology studies on the role of D-2-like dopamine receptors in neuropsychiatric and neurological disorders. Furthermore, compound 20e, which has the highest binding affinity and selectivity for the D-3 receptor (K-i = 0.17 nM for D-3, 163-fold selectivity for D-3 VS D-2 receptors), represents a candidate fluorine-18 radiotracer for in vivo PET imaging studies on the regulation of D-3 receptor expression.
• Synthesis and 5-HT-3 receptor binding activity of 5-[125I]iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide and its 5-halogen-2-alkoxyl homologues
  作者：T de Paulis、WA Hewlett、DE Schmidt、NS Mason、BL Trivedi、MH Ebert

  DOI：10.1016/s0223-5234(97)81676-5

  日期：1997.5

  (S)-5-Iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (MIZAC) was prepared from 5-iodo-2,3-dimethoxybenzoyl chloride and (S)-3-aminoquinuclidine. [I-125]Iodode-stannylation of its corresponding 5-tri-n-butyltin derivative gave [I-125]-MIZAC at 1800 Ci/mmol. Binding of [I-125]-MIZAC in rat entorhinal cortex revealed a K-D of 1.37 +/- 0.21 nM. A series of racemic 2-O-alkyl derivatives of MIZAC were prepared and 5-HT-3 receptor affinities were determined by inhibition of [I-125]-MIZAC binding. Optimal affinity for the receptor was obtained with small, electron-withdrawing substituents in the aromatic 5-position and with bulky substituents in the 3-position. [I-125]-MIZAC is a selective radioligand useful for in vitro identification of the 5-HT-3 receptor.