(RS)-1-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-<4-<2-(3-methylpiperidin-1-yl)-1,2-diazaethylen-1-yl>phenyl>-α-phenylacetate | 81381-92-2

• 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: (RS)-1-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-<4-<2-(3-methylpiperidin-1-yl)-1,2-diazaethylen-1-yl>phenyl>-α-phenylacetate
• 英文别名: (RS)-1-azabicyclo[2.2.2]oct-3-yl (RS)-α-hydroxy-α-{4-[2-(3-methylpiperidin-1-yl)-1,2-diazaethylen-1-yl]phenyl}-α-phenylacetate；1-Azabicyclo[2.2.2]oct-3-yl hydroxy(4-((3-methyl-1-piperidinyl)diazenyl)phenyl)phenylacetate；1-azabicyclo[2.2.2]octan-3-yl 2-hydroxy-2-[4-[(3-methylpiperidin-1-yl)diazenyl]phenyl]-2-phenylacetate
• CAS: 81381-92-2
• 化学式: C₂₇H₃₄N₄O₃
• 分子量: 462.592
• InChiKey: SZTCVIJRGVLUNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (RS)-1-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-<4-<2-(3-methylpiperidin-1-yl)-1,2-diazaethylen-1-yl>phenyl>-α-phenylacetate 在 甲烷磺酸 、 2,2,2-三氟乙醇 、 sodium iodide 作用下， 反应 0.75h， 以54%的产率得到3-奎宁环基 4-碘二苯羟乙酸酯
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated derivatives of 1-azabicyclo[2.2.2]oct-3-yl .alpha.-hydroxy-.alpha.-(4-iodophenyl)-.alpha.-phenylacetate as potential radiopharmaceuticals

  摘要：

  Two derivatives of (RS)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetate (1a) and three partially resolved (R)- or (S)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetates labeled with no carrier added iodine-125 (1b, 18, and 19) and iodine-123 (1c and 18a) were synthesized by the Wallach triazene approach. We have found that this approach is necessary to obtain no carrier added labeling and gives far better results than the direct electrophilic iodination. The obtained yields were 7 to 18% when using iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-125 labeled compounds. Our preliminary distribution studies indicate that 1b localizes in the organs known to have a large concentration of muscarinic receptors and that this localization is due to binding to those receptors.

  DOI：

  10.1021/jm00368a009
• 作为产物：
  描述：

  1-(4-氨基苯基)-2-苯基乙烷-1,2-二酮 在 盐酸 、 sodium hydroxide 、 硫酸 、 sodium 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 反应 54.08h， 生成 (RS)-1-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-<4-<2-(3-methylpiperidin-1-yl)-1,2-diazaethylen-1-yl>phenyl>-α-phenylacetate
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated derivatives of 1-azabicyclo[2.2.2]oct-3-yl .alpha.-hydroxy-.alpha.-(4-iodophenyl)-.alpha.-phenylacetate as potential radiopharmaceuticals

  摘要：

  Two derivatives of (RS)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetate (1a) and three partially resolved (R)- or (S)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetates labeled with no carrier added iodine-125 (1b, 18, and 19) and iodine-123 (1c and 18a) were synthesized by the Wallach triazene approach. We have found that this approach is necessary to obtain no carrier added labeling and gives far better results than the direct electrophilic iodination. The obtained yields were 7 to 18% when using iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-125 labeled compounds. Our preliminary distribution studies indicate that 1b localizes in the organs known to have a large concentration of muscarinic receptors and that this localization is due to binding to those receptors.

  DOI：

  10.1021/jm00368a009

文献信息

• Synthesis and evaluation of radioiodinated derivatives of 1-azabicyclo[2.2.2]oct-3-yl .alpha.-hydroxy-.alpha.-(4-iodophenyl)-.alpha.-phenylacetate as potential radiopharmaceuticals
  作者：W. J. Rzeszotarski、W. C. Eckelman、B. E. Francis、D. A. Simms、R. E. Gibson、E. M. Jagoda、M. P. Grissom、R. R. Eng、J. J. Conklin、R. C. Reba

  DOI：10.1021/jm00368a009

  日期：1984.2

  Two derivatives of (RS)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetate (1a) and three partially resolved (R)- or (S)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetates labeled with no carrier added iodine-125 (1b, 18, and 19) and iodine-123 (1c and 18a) were synthesized by the Wallach triazene approach. We have found that this approach is necessary to obtain no carrier added labeling and gives far better results than the direct electrophilic iodination. The obtained yields were 7 to 18% when using iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-125 labeled compounds. Our preliminary distribution studies indicate that 1b localizes in the organs known to have a large concentration of muscarinic receptors and that this localization is due to binding to those receptors.