(4-hydroxy-3-iodophenyl)(4-nitrophenyl)methanone | 1359168-18-5

• 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: (4-hydroxy-3-iodophenyl)(4-nitrophenyl)methanone
• CAS: 1359168-18-5
• 化学式: C₁₃H₈INO₄
• 分子量: 369.115
• InChiKey: NXIOKMYSKCNMTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.44
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4-hydroxy-3-iodophenyl)(4-nitrophenyl)methanone 、 3-丁炔-2-(R)-甲基吡咯烷 在 copper(l) iodide 、 palladium diacetate 、 三对苯甲基膦 、 二异丙胺 作用下， 以 乙腈 为溶剂， 反应 26.0h， 以28%的产率得到(R)-(2-(2-(2-methylpyrrolidin-1-yl)ethyl)benzofuran-5-yl)(4-nitrophenyl)methanone
  参考文献：
  名称：

  Radiosynthesis and Evaluation of an ¹⁸F-Labeled Positron Emission Tomography (PET) Radioligand for Brain Histamine Subtype-3 Receptors Based on a Nonimidazole 2-Aminoethylbenzofuran Chemotype

  摘要：

  A known chemotype of H-3 receptor ligand was explored for development of a radioligand for imaging brain histamine subtype 3 (H-3) receptors in vivo with positron emission tomography (PET), namely nonimidazole 2-aminoethylbenzofurans, represented by the compound (R)-(2-(2-(2-methylpyrrolidin-1-yl)ethyl)benzofuran-5-yl)(4-fluorophenyl)-methanone (9). Compound 9 was labeled with fluorine-18 (t(1/2) = 109.7 min) in high specific activity by treating the prepared nitro analogue (12) with cyclotron-produced [F-18]-fluoride ion. [F-18]9 was studied with PET in mouse and in monkey after intravenous injection. [F-18]9 showed favorable properties as a candidate PET radioligand, including moderately high brain uptake with a high proportion of H-3 receptor-specific signal in the absence of radiodefluorination. The nitro compound 12 was found to have even higher H-3 receptor affinity, indicating the potential of this chemotype for the development of further promising PET ralioligands.

  DOI：

  10.1021/jm201690h
• 作为产物：
  描述：

  4-羟基-4-硝基苯甲酮 在 ammonium hydroxide 、 碘 、 potassium iodide 作用下， 以 水 为溶剂， 反应 48.0h， 以26%的产率得到(4-hydroxy-3-iodophenyl)(4-nitrophenyl)methanone
  参考文献：
  名称：

  Radiosynthesis and Evaluation of an ¹⁸F-Labeled Positron Emission Tomography (PET) Radioligand for Brain Histamine Subtype-3 Receptors Based on a Nonimidazole 2-Aminoethylbenzofuran Chemotype

  摘要：

  A known chemotype of H-3 receptor ligand was explored for development of a radioligand for imaging brain histamine subtype 3 (H-3) receptors in vivo with positron emission tomography (PET), namely nonimidazole 2-aminoethylbenzofurans, represented by the compound (R)-(2-(2-(2-methylpyrrolidin-1-yl)ethyl)benzofuran-5-yl)(4-fluorophenyl)-methanone (9). Compound 9 was labeled with fluorine-18 (t(1/2) = 109.7 min) in high specific activity by treating the prepared nitro analogue (12) with cyclotron-produced [F-18]-fluoride ion. [F-18]9 was studied with PET in mouse and in monkey after intravenous injection. [F-18]9 showed favorable properties as a candidate PET radioligand, including moderately high brain uptake with a high proportion of H-3 receptor-specific signal in the absence of radiodefluorination. The nitro compound 12 was found to have even higher H-3 receptor affinity, indicating the potential of this chemotype for the development of further promising PET ralioligands.

  DOI：

  10.1021/jm201690h