1-methyl-2-phenyl-3,4-bis<<(N-2-propylcarbamoyl)oxy>methyl>-3-pyrroline | 104156-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 1-methyl-2-phenyl-3,4-bis<<(N-2-propylcarbamoyl)oxy>methyl>-3-pyrroline
• 英文别名: 1-methyl-2-phenyl-3,4-bis[[(N-propylcarbamoyl)oxy]methyl]-3-pyrroline；[1-methyl-5-phenyl-4-(propan-2-ylcarbamoyloxymethyl)-2,5-dihydropyrrol-3-yl]methyl N-propan-2-ylcarbamate
• CAS: 104156-41-4
• 化学式: C₂₁H₃₁N₃O₄
• 分子量: 389.495
• InChiKey: NIMTXERRUJKTCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methyl-2-phenyl-3,4-bis<<(N-2-propylcarbamoyl)oxy>methyl>-3-pyrroline 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以54%的产率得到1-methyl-2-phenyl-3,4-bis[[(N-propylcarbamoyl)oxy]methyl]-3-pyrroline 1-oxide
  参考文献：
  名称：

  3-Pyrroline N-oxide bis(carbamate) tumor inhibitors as analogs of indicine N-oxide

  摘要：

  The 2,3-bis[[(N-methylcarbamoyl)oxy]methyl]-3-pyrroline 1-oxide 5 was synthesized and tested in the murine P388 lymphocytic leukemia model. The compound showed significant reproducible activity and was more potent than indicine N-oxide. 1-Methyl-2-phenyl-3,4-bis[[(N-2- propylcarbamoyl)oxy]methyl]-3-pyrroline N-oxide (6) was less active than 5, and the 5,5-dimethyl analogue of 6, the pyrroline N-oxide 7, was inactive. The N-oxide 7 cannot be converted to a pyrrole in vivo because of the gem-dimethyl substitution at C-5.

  DOI：

  10.1021/jm00394a036
• 作为产物：
  描述：

  Trifluoro-methanesulfonatemethyl-[1-phenyl-meth-(Z)-ylidene]-trimethylsilanylmethyl-ammonium; 在 dibutyltin diacetate 、 二异丁基氢化铝 、 cesium fluoride 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 33.0h， 生成 1-methyl-2-phenyl-3,4-bis<<(N-2-propylcarbamoyl)oxy>methyl>-3-pyrroline
  参考文献：
  名称：

  Vinylogous carbinolamine tumor inhibitors. 19. Synthesis and antineoplastic activity of bis[[[(alkylamino)carbonyl]oxy]methyl]-substituted 3-pyrrolines as prodrugs of tumor inhibitory pyrrolebis(carbamates)

  摘要：

  A series of bis[(carbamoyloxy)methyl]pyrrolines 2-4 were synthesized from either the appropriate alpha-silylated iminium salt, or an aziridine, or a 2H-azirine in a sequence involving 1,3-dipolar cycloaddition reactions. The antineoplastic activities of the pyrrolines were compared to the corresponding pyrroles. The C-2 gem-dimethyl-substituted pyrroline, 4, which cannot be converted to the pyrrole in vivo, was inactive. The activity of the 2-phenyl-substituted pyrrolines 3 was markedly dependent on the nature of the phenyl substituent, although the corresponding phenylpyrroles all showed comparable activity. The differences in the activities of the pyrrolines 3 may be due to the rate of metabolic conversion of the pyrroline to the pyrrole. Electron-withdrawing substituents on the phenyl ring appear to retard this process.

  DOI：

  10.1021/jm00161a019

文献信息

• ANDERSON, WAYNE K.;MILOWSKY, ARNOLD S., J. MED. CHEM., 30,(1987) N 11, 2144-2147
  作者：ANDERSON, WAYNE K.、MILOWSKY, ARNOLD S.

  DOI：——

  日期：——
• ANDERSON W. K.; MILOWSKY A. S., J. MED. CHEM., 29,(1986) N 11, 2241-2249
  作者：ANDERSON W. K.、 MILOWSKY A. S.

  DOI：——

  日期：——
• Vinylogous carbinolamine tumor inhibitors. 19. Synthesis and antineoplastic activity of bis[[[(alkylamino)carbonyl]oxy]methyl]-substituted 3-pyrrolines as prodrugs of tumor inhibitory pyrrolebis(carbamates)
  作者：Wayne K. Anderson、Arnold S. Milowsky

  DOI：10.1021/jm00161a019

  日期：1986.11

  A series of bis[(carbamoyloxy)methyl]pyrrolines 2-4 were synthesized from either the appropriate alpha-silylated iminium salt, or an aziridine, or a 2H-azirine in a sequence involving 1,3-dipolar cycloaddition reactions. The antineoplastic activities of the pyrrolines were compared to the corresponding pyrroles. The C-2 gem-dimethyl-substituted pyrroline, 4, which cannot be converted to the pyrrole in vivo, was inactive. The activity of the 2-phenyl-substituted pyrrolines 3 was markedly dependent on the nature of the phenyl substituent, although the corresponding phenylpyrroles all showed comparable activity. The differences in the activities of the pyrrolines 3 may be due to the rate of metabolic conversion of the pyrroline to the pyrrole. Electron-withdrawing substituents on the phenyl ring appear to retard this process.
• 3-Pyrroline N-oxide bis(carbamate) tumor inhibitors as analogs of indicine N-oxide
  作者：Wayne K. Anderson、Arnold S. Milowsky

  DOI：10.1021/jm00394a036

  日期：1987.11

  The 2,3-bis[[(N-methylcarbamoyl)oxy]methyl]-3-pyrroline 1-oxide 5 was synthesized and tested in the murine P388 lymphocytic leukemia model. The compound showed significant reproducible activity and was more potent than indicine N-oxide. 1-Methyl-2-phenyl-3,4-bis[[(N-2- propylcarbamoyl)oxy]methyl]-3-pyrroline N-oxide (6) was less active than 5, and the 5,5-dimethyl analogue of 6, the pyrroline N-oxide 7, was inactive. The N-oxide 7 cannot be converted to a pyrrole in vivo because of the gem-dimethyl substitution at C-5.