1-methyl-1,2,3,6-tetrahydropyridin-4-yl bis(2-chloroethyl)phosphoramidochloridate | 195813-73-1

• 英文名称: 1-methyl-1,2,3,6-tetrahydropyridin-4-yl bis(2-chloroethyl)phosphoramidochloridate
• CAS: 195813-73-1
• 化学式: C₁₀H₁₈Cl₃N₂O₂P
• 分子量: 335.598
• InChiKey: YSVUVFZOIKEVKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  32.78
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-methyl-1,2,3,6-tetrahydropyridin-4-yl bis(2-chloroethyl)phosphoramidochloridate 在 氨 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 1-methyl-1,2,3,6-tetrahydro-4-pyridyl-N,N-bis(2-chloroethyl)phosphorodiamidate
  参考文献：
  名称：

  Potential latent nitrogen mustard derivatives designed to target monoamine oxidase rich cells

  摘要：

  The monoamine oxidases A and B (MAO-A and MAO-B) catalyze the alpha-carbon oxidation of a variety of 4-substituted 1-methyl-1,2,3,6-tetrahydropyridine derivatives to yield the corresponding 2,3-dihydropyridinium species. When the substituent at C-4 of the tetrahydropyridine moiety is a carbamoyloxy functionality, the resulting dihydropyridinium metabolite undergoes spontaneous hydrolytic cleavage to yield 1-methyl-5,6-dihydro-4-pyridone, CO2, and the corresponding secondary amine. In this paper we summarize our efforts to exploit this metabolic pathway to develop latent nitrogen mustard derivatives related to the oxazaphosphorine antitumor agent cyclophosphamide which may target MAO-A and/or MAO-B rich cells. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00056-4
• 作为产物：
  描述：

  双(2-氯乙基)氨基磷酰二氯 、 1-Methyl-4-((trimethylsilyl)oxy)-1,2,3,6-tetrahydropyridine 在 甲基锂 作用下， 生成 1-methyl-1,2,3,6-tetrahydropyridin-4-yl bis(2-chloroethyl)phosphoramidochloridate
  参考文献：
  名称：

  Potential latent nitrogen mustard derivatives designed to target monoamine oxidase rich cells

  摘要：

  The monoamine oxidases A and B (MAO-A and MAO-B) catalyze the alpha-carbon oxidation of a variety of 4-substituted 1-methyl-1,2,3,6-tetrahydropyridine derivatives to yield the corresponding 2,3-dihydropyridinium species. When the substituent at C-4 of the tetrahydropyridine moiety is a carbamoyloxy functionality, the resulting dihydropyridinium metabolite undergoes spontaneous hydrolytic cleavage to yield 1-methyl-5,6-dihydro-4-pyridone, CO2, and the corresponding secondary amine. In this paper we summarize our efforts to exploit this metabolic pathway to develop latent nitrogen mustard derivatives related to the oxazaphosphorine antitumor agent cyclophosphamide which may target MAO-A and/or MAO-B rich cells. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00056-4