3-(phenylseleno)-2,5-pyrrolidinedione | 77405-81-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(phenylseleno)-2,5-pyrrolidinedione
• 英文别名: 3-Phenylselanylpyrrolidine-2,5-dione
• CAS: 77405-81-3
• 化学式: C₁₀H₉NO₂Se
• 分子量: 254.147
• InChiKey: DQQDOJQRECYIDS-UHFFFAOYSA-N

物化性质

• 沸点：
  438.4±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(phenylseleno)-2,5-pyrrolidinedione 在 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 27.0h， 生成 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,5-dioxo-3-(phenylselanyl)pyrrolidin-1-yl)tetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Showdomycin analogs: synthesis and antitumor evaluation

  摘要：

  The synthesis of N-beta-D-ribofuranosyl derivatives of maleimide, 3-methylmaleimide, and 3-chloromaleimide was accomplished in three steps from ribosylamine. The synthetic ribosides can be considered N-nucleoside analogues of showdomycin, which is an antitumor antibiotic of the C-nucleoside type. Although the three analogues were cytotoxic to cultured L1210 cells, no in vivo antitumor activity was found with the murine P388 leukemia test system. Drug transport studies were done in an attempt to trace the biological fate of the analogues.

  DOI：

  10.1021/jm00137a008
• 作为产物：
  描述：

  马来酰亚胺 、 苯硒酚 以 乙醚 为溶剂， 反应 2.0h， 以81%的产率得到3-(phenylseleno)-2,5-pyrrolidinedione
  参考文献：
  名称：

  Showdomycin analogs: synthesis and antitumor evaluation

  摘要：

  The synthesis of N-beta-D-ribofuranosyl derivatives of maleimide, 3-methylmaleimide, and 3-chloromaleimide was accomplished in three steps from ribosylamine. The synthetic ribosides can be considered N-nucleoside analogues of showdomycin, which is an antitumor antibiotic of the C-nucleoside type. Although the three analogues were cytotoxic to cultured L1210 cells, no in vivo antitumor activity was found with the murine P388 leukemia test system. Drug transport studies were done in an attempt to trace the biological fate of the analogues.

  DOI：

  10.1021/jm00137a008

文献信息

• Showdomycin analogs: synthesis and antitumor evaluation
  作者：Naganori Numao、Hiromichi Hemmi、Saulius A. Naujokaitis、Marco Rabinovitz、John A. Beisler

  DOI：10.1021/jm00137a008

  日期：1981.5

  The synthesis of N-beta-D-ribofuranosyl derivatives of maleimide, 3-methylmaleimide, and 3-chloromaleimide was accomplished in three steps from ribosylamine. The synthetic ribosides can be considered N-nucleoside analogues of showdomycin, which is an antitumor antibiotic of the C-nucleoside type. Although the three analogues were cytotoxic to cultured L1210 cells, no in vivo antitumor activity was found with the murine P388 leukemia test system. Drug transport studies were done in an attempt to trace the biological fate of the analogues.