苯乙胺,N,3,4-三甲基-a-2-丙烯-1-基- | 97807-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 苯乙胺,N,3,4-三甲基-a-2-丙烯-1-基-
• 英文名称: 1-methyl-3-carbamoyl>pyridinium iodide
• 英文别名: 1-methyl-3-{N-[β-(4-iodophenyl)ethyl]carbamoyl}pyridinium iodide；N-[2-(4-Iodophenyl)ethyl]-1-methylpyridin-1-ium-3-carboximidate--hydrogen iodide (1/1)；N-[2-(4-iodophenyl)ethyl]-1-methylpyridin-1-ium-3-carboximidate;hydroiodide
• CAS: 97807-21-1
• 化学式: C₁₅H₁₆IN₂O*I
• 分子量: 494.114
• InChiKey: QQSQBRYPSIITRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.91
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  33
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯乙胺,N,3,4-三甲基-a-2-丙烯-1-基- 在 sodium dithionite 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以78%的产率得到1-methyl-3-{N-[β-(4-iodophenyl)ethyl]carbamoyl}-1,4-dihydropyridine
  参考文献：
  名称：

  Evaluation of the brain-specific delivery of radioiodinated (Iodophenyl) alkyl-substituted amines coupled to a dihydropyridine carrier

  摘要：

  To evaluate the potential usefulness of radioiodinated phenylamines attached to dihydropyridine carriers as a means of brain-specific delivery of radiopharmaceuticals, 1-methyl-3-[N-[beta- (4-[125I]iodophenyl)ethyl]carbamoyl]-1,4-dihydropyridine ([125I]-9) and 1-methyl-3-[N-(4-[125I]iodophenyl)carbamoyl]-1,4-dihydropyridine ([125I]-13) have been prepared by dithionite reduction of the corresponding pyridinium precursors, [125I]-8 and [125I]-12, respectively. Formation of 8 involved coupling of (p-aminophenyl)ethylamine with N-succinimidyl (1-methyl-3-pyridinio)formate iodide (4) followed by transformation to the corresponding N-piperidinyl- (6) or (diethylamino)- (7) triazines that were converted to 8 by treatment with HI. Alternatively, 12 was prepared by initial conversion of (4-amino-phenyl)mercuric acetate (10) to 4-iodoaniline (11) by treatment with I2 and then coupling with 4. The radioiodinated quaternary products, 8 and 12, showed low brain uptake and low brain to blood ratios, whereas the dihydropyridine analogues, 9 and 13, showed comparatively good brain uptake and good brain to blood ratios in rats. These data demonstrate that dihydropyridine-coupled radiopharmaceuticals can cross the blood-brain barrier and the technique may be useful for the measurement of cerebral blood perfusion.

  DOI：

  10.1021/jm00149a006
• 作为产物：
  描述：

  2-(4-氨基苯)乙胺 在 氢氟酸 、 potassium carbonate 、 sodium iodide 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 14.0h， 生成 苯乙胺,N,3,4-三甲基-a-2-丙烯-1-基-
  参考文献：
  名称：

  Evaluation of the brain-specific delivery of radioiodinated (Iodophenyl) alkyl-substituted amines coupled to a dihydropyridine carrier

  摘要：

  To evaluate the potential usefulness of radioiodinated phenylamines attached to dihydropyridine carriers as a means of brain-specific delivery of radiopharmaceuticals, 1-methyl-3-[N-[beta- (4-[125I]iodophenyl)ethyl]carbamoyl]-1,4-dihydropyridine ([125I]-9) and 1-methyl-3-[N-(4-[125I]iodophenyl)carbamoyl]-1,4-dihydropyridine ([125I]-13) have been prepared by dithionite reduction of the corresponding pyridinium precursors, [125I]-8 and [125I]-12, respectively. Formation of 8 involved coupling of (p-aminophenyl)ethylamine with N-succinimidyl (1-methyl-3-pyridinio)formate iodide (4) followed by transformation to the corresponding N-piperidinyl- (6) or (diethylamino)- (7) triazines that were converted to 8 by treatment with HI. Alternatively, 12 was prepared by initial conversion of (4-amino-phenyl)mercuric acetate (10) to 4-iodoaniline (11) by treatment with I2 and then coupling with 4. The radioiodinated quaternary products, 8 and 12, showed low brain uptake and low brain to blood ratios, whereas the dihydropyridine analogues, 9 and 13, showed comparatively good brain uptake and good brain to blood ratios in rats. These data demonstrate that dihydropyridine-coupled radiopharmaceuticals can cross the blood-brain barrier and the technique may be useful for the measurement of cerebral blood perfusion.

  DOI：

  10.1021/jm00149a006

文献信息

• Evaluation of the brain-specific delivery of radioiodinated (Iodophenyl) alkyl-substituted amines coupled to a dihydropyridine carrier
  作者：M. L. Tedjamulia、P. C. Srivastava、F. F. Knapp

  DOI：10.1021/jm00149a006

  日期：1985.11

  To evaluate the potential usefulness of radioiodinated phenylamines attached to dihydropyridine carriers as a means of brain-specific delivery of radiopharmaceuticals, 1-methyl-3-[N-[beta- (4-[125I]iodophenyl)ethyl]carbamoyl]-1,4-dihydropyridine ([125I]-9) and 1-methyl-3-[N-(4-[125I]iodophenyl)carbamoyl]-1,4-dihydropyridine ([125I]-13) have been prepared by dithionite reduction of the corresponding pyridinium precursors, [125I]-8 and [125I]-12, respectively. Formation of 8 involved coupling of (p-aminophenyl)ethylamine with N-succinimidyl (1-methyl-3-pyridinio)formate iodide (4) followed by transformation to the corresponding N-piperidinyl- (6) or (diethylamino)- (7) triazines that were converted to 8 by treatment with HI. Alternatively, 12 was prepared by initial conversion of (4-amino-phenyl)mercuric acetate (10) to 4-iodoaniline (11) by treatment with I2 and then coupling with 4. The radioiodinated quaternary products, 8 and 12, showed low brain uptake and low brain to blood ratios, whereas the dihydropyridine analogues, 9 and 13, showed comparatively good brain uptake and good brain to blood ratios in rats. These data demonstrate that dihydropyridine-coupled radiopharmaceuticals can cross the blood-brain barrier and the technique may be useful for the measurement of cerebral blood perfusion.