1-methyl-3,4-diphenyl-2,5-bis(hydroxymethyl)pyrrole | 103776-14-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-methyl-3,4-diphenyl-2,5-bis(hydroxymethyl)pyrrole
• 英文别名: [5-(hydroxymethyl)-1-methyl-3,4-diphenylpyrrol-2-yl]methanol
• CAS: 103776-14-3
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: BJPDLVDUXBPLNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  45.39
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-methyl-3,4-diphenyl-2,5-bis(hydroxymethyl)pyrrole 、 异氰酸异丙酯 在 dibutyltin diacetate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以79%的产率得到1-methyl-3,4-diphenyl-2,5-bis(hydroxymethyl)pyrrole bis
  参考文献：
  名称：

  Vinylogous carbinolamine tumor inhibitors. 20. Comparison of the chemical reactivities and antineoplastic activities of .alpha.,.beta.-, .alpha.,.beta.'-, .beta.,.beta.'- and .alpha.,.alpha.'-bis[[[(2-propylamino)carbonyl]oxy]methyl] substituted pyrroles

  摘要：

  The bis[N-(2-propyl)carbamate] derivatives of 2,3-bis(hydroxymethyl)-4,5-diphenyl-1-methylpyrrole (4a), 3,4-bis-(hydroxymethyl)-2,5-diphenyl-1-methylpyrrole (4b), 2,4-bis(hydroxymethyl)-3,5-diphenyl-1-methylpyrrole (4c), and 2,5-bis(hydroxymethyl)-3,4-diphenyl-1-methylpyrrole (4d) were synthesized and the reactivities of the four compounds were compared using the model nucleophile 4-(p-nitrobenzyl)pyridine (NBP). No significant correlation was seen between NBP reactivity and either toxicity or antineoplastic activity in this series. Three compounds 4a, 4b, and 4c gave significant reproducible activity against P388 lymphocytic leukemia; the alpha,alpha'-bis(carbamate) 4d was inactive. The alpha,beta- and alpha,beta'-bis(carbamates) 4a and 4c were evaluated against a panel of mouse tumor homografts and human tumor xenografts implanted under the kidney capsule of mice.

  DOI：

  10.1021/jm00161a042
• 作为产物：
  描述：

  3,4-diphenyl-1H-pyrrole-2,5-dicarboxylic acid 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 生成 1-methyl-3,4-diphenyl-2,5-bis(hydroxymethyl)pyrrole
  参考文献：
  名称：

  Vinylogous carbinolamine tumor inhibitors. 20. Comparison of the chemical reactivities and antineoplastic activities of .alpha.,.beta.-, .alpha.,.beta.'-, .beta.,.beta.'- and .alpha.,.alpha.'-bis[[[(2-propylamino)carbonyl]oxy]methyl] substituted pyrroles

  摘要：

  The bis[N-(2-propyl)carbamate] derivatives of 2,3-bis(hydroxymethyl)-4,5-diphenyl-1-methylpyrrole (4a), 3,4-bis-(hydroxymethyl)-2,5-diphenyl-1-methylpyrrole (4b), 2,4-bis(hydroxymethyl)-3,5-diphenyl-1-methylpyrrole (4c), and 2,5-bis(hydroxymethyl)-3,4-diphenyl-1-methylpyrrole (4d) were synthesized and the reactivities of the four compounds were compared using the model nucleophile 4-(p-nitrobenzyl)pyridine (NBP). No significant correlation was seen between NBP reactivity and either toxicity or antineoplastic activity in this series. Three compounds 4a, 4b, and 4c gave significant reproducible activity against P388 lymphocytic leukemia; the alpha,alpha'-bis(carbamate) 4d was inactive. The alpha,beta- and alpha,beta'-bis(carbamates) 4a and 4c were evaluated against a panel of mouse tumor homografts and human tumor xenografts implanted under the kidney capsule of mice.

  DOI：

  10.1021/jm00161a042

文献信息

• ANDERSON W. K.; HEIDER A. R., J. MED. CHEM., 29,(1986) N 11, 2392-2395
  作者：ANDERSON W. K.、 HEIDER A. R.

  DOI：——

  日期：——
• Vinylogous carbinolamine tumor inhibitors. 20. Comparison of the chemical reactivities and antineoplastic activities of .alpha.,.beta.-, .alpha.,.beta.'-, .beta.,.beta.'- and .alpha.,.alpha.'-bis[[[(2-propylamino)carbonyl]oxy]methyl] substituted pyrroles
  作者：Wayne K. Anderson、Arvela R. Heider

  DOI：10.1021/jm00161a042

  日期：1986.11

  The bis[N-(2-propyl)carbamate] derivatives of 2,3-bis(hydroxymethyl)-4,5-diphenyl-1-methylpyrrole (4a), 3,4-bis-(hydroxymethyl)-2,5-diphenyl-1-methylpyrrole (4b), 2,4-bis(hydroxymethyl)-3,5-diphenyl-1-methylpyrrole (4c), and 2,5-bis(hydroxymethyl)-3,4-diphenyl-1-methylpyrrole (4d) were synthesized and the reactivities of the four compounds were compared using the model nucleophile 4-(p-nitrobenzyl)pyridine (NBP). No significant correlation was seen between NBP reactivity and either toxicity or antineoplastic activity in this series. Three compounds 4a, 4b, and 4c gave significant reproducible activity against P388 lymphocytic leukemia; the alpha,alpha'-bis(carbamate) 4d was inactive. The alpha,beta- and alpha,beta'-bis(carbamates) 4a and 4c were evaluated against a panel of mouse tumor homografts and human tumor xenografts implanted under the kidney capsule of mice.