4-(2,4-dichlorophenoxy)-1-methylpyridinium iodide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2,4-dichlorophenoxy)-1-methylpyridinium iodide
• 英文别名: 4-(2,4-Dichlorophenoxy)-1-methylpyridin-1-ium;iodide
• 化学式: C₁₂H₁₀Cl₂NO*I
• 分子量: 382.028
• InChiKey: KLOLPLHNYFLTGH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2,4-dichlorophenoxy)-1-methylpyridinium iodide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 4-(2,4-dichlorophenoxy)-1-methyl-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  Novel 4-(Aryloxy)tetrahydropyridine Analogs of MPTP as Monoamine Oxidase A and B Substrates

  摘要：

  The exceptionally good monoamine oxidase (MAO) substrate properties of several 4-(arylmethyl)-1-methyl-1,2,3,6-tetrahydropyridine derivatives related to the neurotoxin MPTP have prompted studies to evaluate the corresponding properties of tetrahydropyridine derivatives bearing heteroatom-linked groups at C-4. The expected dihydropyridinium metabolites generated from these MAO-A- and MAO-B-catalyzed oxidations of the 4-(aryloxy)tetrahydropyridine analogs were found to undergo rapid hydrolytic cleavage to yield the corresponding arenol and 1-methyl-2,3-dihydro-4-pyridone, a species that could be monitored spectrophotometrically. We have exploited this reaction sequence to probe the active sites of beef liver MAO-B and human placental MAO-A with a variety of 4-(aryloxy)-1-methyl-1,2,3,6-tetrahydropyridine derivatives. The results are discussed in relationship to recently published reports describing the MAO-A vs MAO-B selectivity of various 4-(arylmethyl)tetrahydropyridine derivatives.

  DOI：

  10.1021/jm00033a012
• 作为产物：
  描述：

  4-chloro-1-methylpyridinium iodide 、 2,4-二氯酚 在 三乙胺 作用下， 以 丙酮 为溶剂， 以64%的产率得到4-(2,4-dichlorophenoxy)-1-methylpyridinium iodide
  参考文献：
  名称：

  Novel 4-(Aryloxy)tetrahydropyridine Analogs of MPTP as Monoamine Oxidase A and B Substrates

  摘要：

  The exceptionally good monoamine oxidase (MAO) substrate properties of several 4-(arylmethyl)-1-methyl-1,2,3,6-tetrahydropyridine derivatives related to the neurotoxin MPTP have prompted studies to evaluate the corresponding properties of tetrahydropyridine derivatives bearing heteroatom-linked groups at C-4. The expected dihydropyridinium metabolites generated from these MAO-A- and MAO-B-catalyzed oxidations of the 4-(aryloxy)tetrahydropyridine analogs were found to undergo rapid hydrolytic cleavage to yield the corresponding arenol and 1-methyl-2,3-dihydro-4-pyridone, a species that could be monitored spectrophotometrically. We have exploited this reaction sequence to probe the active sites of beef liver MAO-B and human placental MAO-A with a variety of 4-(aryloxy)-1-methyl-1,2,3,6-tetrahydropyridine derivatives. The results are discussed in relationship to recently published reports describing the MAO-A vs MAO-B selectivity of various 4-(arylmethyl)tetrahydropyridine derivatives.

  DOI：

  10.1021/jm00033a012

文献信息

• Kalgutkar Amit S., Castagnoli Kay, Hall Andrea, Castagnoli Neal, J. Med. Chem, 37 (1994) N 7, S 944-949
  作者：Kalgutkar Amit S., Castagnoli Kay, Hall Andrea, Castagnoli Neal

  DOI：——

  日期：——
• Novel 4-(Aryloxy)tetrahydropyridine Analogs of MPTP as Monoamine Oxidase A and B Substrates
  作者：Amit S. Kalgutkar、Kay Castagnoli、Andrea Hall、Neal Castagnoli

  DOI：10.1021/jm00033a012

  日期：1994.4

  The exceptionally good monoamine oxidase (MAO) substrate properties of several 4-(arylmethyl)-1-methyl-1,2,3,6-tetrahydropyridine derivatives related to the neurotoxin MPTP have prompted studies to evaluate the corresponding properties of tetrahydropyridine derivatives bearing heteroatom-linked groups at C-4. The expected dihydropyridinium metabolites generated from these MAO-A- and MAO-B-catalyzed oxidations of the 4-(aryloxy)tetrahydropyridine analogs were found to undergo rapid hydrolytic cleavage to yield the corresponding arenol and 1-methyl-2,3-dihydro-4-pyridone, a species that could be monitored spectrophotometrically. We have exploited this reaction sequence to probe the active sites of beef liver MAO-B and human placental MAO-A with a variety of 4-(aryloxy)-1-methyl-1,2,3,6-tetrahydropyridine derivatives. The results are discussed in relationship to recently published reports describing the MAO-A vs MAO-B selectivity of various 4-(arylmethyl)tetrahydropyridine derivatives.