甲基2-(2-氟乙氧基)-5-碘苯甲酸酯 | 193882-74-5

• 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: 甲基2-(2-氟乙氧基)-5-碘苯甲酸酯
• 英文名称: methyl 2-(2-fluoroethoxy)-5-iodobenzoate
• 英文别名: methyl 5-iodo-2-(2-fluoroethoxy)benzoate
• CAS: 193882-74-5
• 化学式: C₁₀H₁₀FIO₃
• 分子量: 324.091
• InChiKey: OSQFSXXGWQZJEB-UHFFFAOYSA-N

物化性质

• 沸点：
  362.2±42.0 °C(Predicted)
• 密度：
  1.658±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基2-(2-氟乙氧基)-5-碘苯甲酸酯 在 copper(l) iodide 、 sodium azide 、 bathophenanthrolinedispufonic acid disodium salt 、 1-羟基苯并三唑 、 copper(II) sulfate 、 sodium ascorbate 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 、 N,N'-二甲基乙二胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-5-(4-((dimethylamino)methyl)-1H-1,2,3-triazol-1-yl)-2-(2-fluoroethoxy)benzamide
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationship Studies of Conformationally Flexible Tetrahydroisoquinolinyl Triazole Carboxamide and Triazole Substituted Benzamide Analogues as σ₂ Receptor Ligands

  摘要：

  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.

  DOI：

  10.1021/jm5001453
• 作为产物：
  描述：

  5-碘水杨酸 在 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 甲基2-(2-氟乙氧基)-5-碘苯甲酸酯
  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

• 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.
• 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 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.