1-methyl-2-fluoro-5-<2,3-dihydro-6,7-bis<<(N-2-propylcarbamoyl)oxy>methyl>-1H-pyrrolizin-5-yl>pyridinium trifluoromethanesulfonate | 123412-65-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1-methyl-2-fluoro-5-<2,3-dihydro-6,7-bis<<(N-2-propylcarbamoyl)oxy>methyl>-1H-pyrrolizin-5-yl>pyridinium trifluoromethanesulfonate
• 英文别名: [3-(6-fluoro-1-methylpyridin-1-ium-3-yl)-2-(propan-2-ylcarbamoyloxymethyl)-6,7-dihydro-5H-pyrrolizin-1-yl]methyl N-propan-2-ylcarbamate;trifluoromethanesulfonate
• CAS: 123412-65-7
• 化学式: CF₃O₃S*C₂₃H₃₂FN₄O₄
• 分子量: 596.6
• InChiKey: JWRKQYVRUMCNAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-methyl-2-fluoro-5-<2,3-dihydro-6,7-bis<<(N-2-propylcarbamoyl)oxy>methyl>-1H-pyrrolizin-5-yl>pyridinium trifluoromethanesulfonate 生成 2,3-dihydro-5-(1-methyl-1,2-dihydro-2-oxopyridin-5-yl)-6,7-bis(hydroxymethyl)-1H-pyrrolizine bis(N-2-propylcarbamate)
  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：

  2,3-dihydro-5-(2-fluoropyridin-5-yl)-6,7-bis(hydroxymethyl)-1H-pyrrolizine bis(N-2-propylcarbamate) 、 三氟甲烷磺酸甲酯 生成 1-methyl-2-fluoro-5-<2,3-dihydro-6,7-bis<<(N-2-propylcarbamoyl)oxy>methyl>-1H-pyrrolizin-5-yl>pyridinium 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：

文献信息

• Vinylogous carbinolamine tumor inhibitors. 24. Synthesis, chemistry, and antineoplastic activity of .alpha.-halopyridinium salts: potential pyridone prodrugs of acylated vinylogous carbinolamine tumor inhibitors.
  作者：Wayne K. Anderson、Dennis C. Dean、Toshiyasu Endo

  DOI：10.1021/jm00168a021

  日期：1990.6

  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.