1-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-piperazine-2,6-dione | 1421691-43-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-piperazine-2,6-dione
• 英文别名: 1-[3-(2-Oxo-pyrrolidin-1-yl)-propyl]-piperazine-2,6-dione；1-[3-(2-oxopyrrolidin-1-yl)propyl]piperazine-2,6-dione
• CAS: 1421691-43-1
• 化学式: C₁₁H₁₇N₃O₃
• 分子量: 239.274
• InChiKey: PFOVYUUUCNZYBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吲哚-2-羧酸 、 1-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-piperazine-2,6-dione 反应 0.12h， 以83%的产率得到4-(1H-indole-2-carbonyl)-1-[3-(2-oxopyrrolidin-1-yl)-propyl]-piperazine-2,6-dione
  参考文献：
  名称：

  Efficient synthesis of piperazine-2,6-dione and 4-(1H-indole-2-carbonyl)piperazine-2,6-dione derivatives and their evaluation for anticancer activity

  摘要：

  Condensation of iminodiacetic acid 1 with various amines i.e., cyclohexanamine, 1-(3-aminopropyl)imidazole, pyridin-2-ylmethanamine, pyridin-3-ylmethanamine, pyridin-4-ylmethanamine, 2-morpholinoethanamine, thiophen-2-ylmethanamine, 2-(thiophen-2-yl)ethanamine, furan-2-ylmethanamine, 2-(pyrrolidin-1-yl)ethanamine, and 1-(3-aminopropyl) pyrrolidin-2-one 2a-k under microwave irradiation gave the corresponding piperazine-2,6-dione derivatives 3a-k in quantitative yields. Piperazine-2,6-dione derivatives 3a-k on condensation with 1H-indole-2-carboxylic acid under microwave irradiation gave the corresponding 4-(1H-indole-2-carbonyl)piperazine-2,6-dione derivatives 4a-k in quantitative yields. All the synthesized compounds (3a-k & 4a-k) were purified by crystallization and characterized by spectroscopic means. On screening at a concentration of 10 mu M, compounds 3k, 4e, 4i breast (T47D), 4j lung (NCI H-522), 3i colon (HCT-15), 4e ovary (PA-1), and 4g liver (HepG-2) exhibited good anticancer activity.

  DOI：

  10.1007/s00044-012-0438-7
• 作为产物：
  描述：

  1-(3-氨基丙基)-2-吡咯烷酮 、 亚氨基二乙酸 反应 0.05h， 以94%的产率得到1-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-piperazine-2,6-dione
  参考文献：
  名称：

  Efficient synthesis of piperazine-2,6-dione and 4-(1H-indole-2-carbonyl)piperazine-2,6-dione derivatives and their evaluation for anticancer activity

  摘要：

  Condensation of iminodiacetic acid 1 with various amines i.e., cyclohexanamine, 1-(3-aminopropyl)imidazole, pyridin-2-ylmethanamine, pyridin-3-ylmethanamine, pyridin-4-ylmethanamine, 2-morpholinoethanamine, thiophen-2-ylmethanamine, 2-(thiophen-2-yl)ethanamine, furan-2-ylmethanamine, 2-(pyrrolidin-1-yl)ethanamine, and 1-(3-aminopropyl) pyrrolidin-2-one 2a-k under microwave irradiation gave the corresponding piperazine-2,6-dione derivatives 3a-k in quantitative yields. Piperazine-2,6-dione derivatives 3a-k on condensation with 1H-indole-2-carboxylic acid under microwave irradiation gave the corresponding 4-(1H-indole-2-carbonyl)piperazine-2,6-dione derivatives 4a-k in quantitative yields. All the synthesized compounds (3a-k & 4a-k) were purified by crystallization and characterized by spectroscopic means. On screening at a concentration of 10 mu M, compounds 3k, 4e, 4i breast (T47D), 4j lung (NCI H-522), 3i colon (HCT-15), 4e ovary (PA-1), and 4g liver (HepG-2) exhibited good anticancer activity.

  DOI：

  10.1007/s00044-012-0438-7

文献信息

• Efficient synthesis of piperazine-2,6-dione and 4-(1H-indole-2-carbonyl)piperazine-2,6-dione derivatives and their evaluation for anticancer activity
  作者：Sandeep Kumar、Nikhil Kumar、Partha Roy、Sham M. Sondhi

  DOI：10.1007/s00044-012-0438-7

  日期：2013.10

  Condensation of iminodiacetic acid 1 with various amines i.e., cyclohexanamine, 1-(3-aminopropyl)imidazole, pyridin-2-ylmethanamine, pyridin-3-ylmethanamine, pyridin-4-ylmethanamine, 2-morpholinoethanamine, thiophen-2-ylmethanamine, 2-(thiophen-2-yl)ethanamine, furan-2-ylmethanamine, 2-(pyrrolidin-1-yl)ethanamine, and 1-(3-aminopropyl) pyrrolidin-2-one 2a-k under microwave irradiation gave the corresponding piperazine-2,6-dione derivatives 3a-k in quantitative yields. Piperazine-2,6-dione derivatives 3a-k on condensation with 1H-indole-2-carboxylic acid under microwave irradiation gave the corresponding 4-(1H-indole-2-carbonyl)piperazine-2,6-dione derivatives 4a-k in quantitative yields. All the synthesized compounds (3a-k & 4a-k) were purified by crystallization and characterized by spectroscopic means. On screening at a concentration of 10 mu M, compounds 3k, 4e, 4i breast (T47D), 4j lung (NCI H-522), 3i colon (HCT-15), 4e ovary (PA-1), and 4g liver (HepG-2) exhibited good anticancer activity.