1-甲基-3-(N-(4-碘苯基)氨基甲酰基)-1,4-二氢吡啶 | 97807-27-7

• 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: 1-甲基-3-(N-(4-碘苯基)氨基甲酰基)-1,4-二氢吡啶
• 中文别名: 苯乙醇,4-甲基-a-[[(1-甲基乙基)氨基]甲基]-
• 英文名称: 1-methyl-3-[N-(p-iodophenyl)carbamoyl]-1,4-dihydropyridine
• 英文别名: 1-Methyl-3-(N-(4-iodophenyl)carbamoyl)-1,4-dihydropyridine；N-(4-iodophenyl)-1-methyl-4H-pyridine-3-carboxamide
• CAS: 97807-27-7
• 化学式: C₁₃H₁₃IN₂O
• 分子量: 340.164
• InChiKey: ZGFBEHFIMBCYBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为产物：
  描述：

  对氨基苯汞乙酸盐 在 sodium dithionite 、 碘 、 碳酸氢钠 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.08h， 生成 1-甲基-3-(N-(4-碘苯基)氨基甲酰基)-1,4-二氢吡啶
  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

• US4764598A
  申请人：——

  公开号：US4764598A

  公开（公告）日：1988-08-16
• US4814339A
  申请人：——

  公开号：US4814339A

  公开（公告）日：1989-03-21
• US4942165A
  申请人：——

  公开号：US4942165A

  公开（公告）日：1990-07-17
• 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.