dimethyl 1-methyl-2-(4-fluoroyphenyl)pyrrole-3,4-dicarboxylate | 104156-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: dimethyl 1-methyl-2-(4-fluoroyphenyl)pyrrole-3,4-dicarboxylate
• 英文别名: dimethyl 2-(4-fluorophenyl)-1-methylpyrrole-3,4-dicarboxylate
• CAS: 104156-60-7
• 化学式: C₁₅H₁₄FNO₄
• 分子量: 291.279
• InChiKey: ILSMTAJURRGARQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dimethyl 1-methyl-2-(4-fluoroyphenyl)pyrrole-3,4-dicarboxylate 在 lithium aluminium tetrahydride 、 dibutyltin diacetate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 1-methyl-2-(4-fluorophenyl)-3,4-bis<<(N-2-propylcarbamoyl)oxy>methyl>pyrrole
  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
• 作为产物：
  描述：

  甲酸 、 丁炔二酸二甲酯 、 methyl(R)-amino-(4-fluorophenyl)-acetate 在 乙酸酐 作用下， 生成 dimethyl 1-methyl-2-(4-fluoroyphenyl)pyrrole-3,4-dicarboxylate
  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 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：——