5-(1,2-Bis-isopropylcarbamoyloxymethyl-6,7-dihydro-5H-pyrrolizin-3-yl)-3-bromo-2-chloro-1-methyl-pyridinium; iodide | 123412-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯嗪
• 英文名称: 5-(1,2-Bis-isopropylcarbamoyloxymethyl-6,7-dihydro-5H-pyrrolizin-3-yl)-3-bromo-2-chloro-1-methyl-pyridinium; iodide
• 英文别名: [3-(5-bromo-6-chloro-1-methylpyridin-1-ium-3-yl)-2-(propan-2-ylcarbamoyloxymethyl)-6,7-dihydro-5H-pyrrolizin-1-yl]methyl N-propan-2-ylcarbamate;iodide
• CAS: 123412-94-2
• 化学式: C₂₃H₃₁BrClN₄O₄*I
• 分子量: 669.785
• InChiKey: WXSFTXGRLNXJLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  85.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(1,2-Bis-isopropylcarbamoyloxymethyl-6,7-dihydro-5H-pyrrolizin-3-yl)-3-bromo-2-chloro-1-methyl-pyridinium; iodide 在 phosphate buffer 、 水 作用下， 生成 Isopropyl-carbamic acid 3-(5-bromo-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-1-isopropylcarbamoyloxymethyl-6,7-dihydro-5H-pyrrolizin-2-ylmethyl ester
  参考文献：
  名称：

  Vinylogous carbinolamine tumor inhibitors. 24. Synthesis, chemistry, and antineoplastic activity of .alpha.-halopyridinium salts: potential pyridone prodrugs of acylated vinylogous carbinolamine tumor inhibitors.

  摘要：

  A series of 4- and 5-[2,3-dihydro-6,7-bis[[(N-alkylcarbamoyl)oxy]methyl]-1H-pyrrol izin-5- yl]-2-halopyridinium iodides were synthesized. The rates of hydrolysis of the alpha-halopyridinium salts to the corresponding pyridones, and the reactivities of the carbamate moieties were studied as a function of pH, buffer composition, and ionic strength. The 4- and 5-pyrrolizinyl-2-halopyridinium iodides and the corresponding pyridones were evaluated against P388 lymphocytic leukemia in vivo. The alpha-fluoropyridinium compounds were active but the alpha-chloro compounds were not. This activity was correlated with the rates of hydrolysis of the alpha-halopyridinium compounds to the active pyridone. Compounds that were active in the P388 screen were evaluated in L1210 leukemia, M5076 carcinoma, and MX-1 mammary xenograft assays in mice.

  DOI：

  10.1021/jm00168a021