2,3-dihydro-5-(2-chloropyridin-5-yl)-6,7-bis(hydroxymethyl)-1H-pyrrolizine bis(N-2-propylcarbamate) | 123412-61-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,3-dihydro-5-(2-chloropyridin-5-yl)-6,7-bis(hydroxymethyl)-1H-pyrrolizine bis(N-2-propylcarbamate)
• 英文别名: [3-(6-chloropyridin-3-yl)-2-(propan-2-ylcarbamoyloxymethyl)-6,7-dihydro-5H-pyrrolizin-1-yl]methyl N-propan-2-ylcarbamate
• CAS: 123412-61-3
• 化学式: C₂₂H₂₉ClN₄O₄
• 分子量: 448.95
• InChiKey: QJGVROJTACTNIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.48
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-5-(2-chloropyridin-5-yl)-6,7-bis(hydroxymethyl)-1H-pyrrolizine bis(N-2-propylcarbamate) 、 三氟甲烷磺酸甲酯 生成 [3-(6-chloro-1-methylpyridin-1-ium-3-yl)-2-(propan-2-ylcarbamoyloxymethyl)-6,7-dihydro-5H-pyrrolizin-1-yl]methyl N-propan-2-ylcarbamate;trifluoromethanesulfonate
  参考文献：
  名称：

  ANDERSON, WAYNE K.;DEAN, DENNIS C.;ENDO, TOSHIYASU, J. MED. CHEM., 33,(1990) N, C. 1667-1675

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氯吡啶-3-羰酰氯 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 dibutyltin diacetate 、 乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 56.0h， 生成 2,3-dihydro-5-(2-chloropyridin-5-yl)-6,7-bis(hydroxymethyl)-1H-pyrrolizine bis(N-2-propylcarbamate)
  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