benzyl (2-((S)-3-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)-2,6-dioxopiperidin-1-yl)acetyl)glycinate | 1246685-63-1

• 英文名称: benzyl (2-((S)-3-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)-2,6-dioxopiperidin-1-yl)acetyl)glycinate
• CAS: 1246685-63-1
• 化学式: C₃₀H₃₆N₄O₈
• 分子量: 580.638
• InChiKey: BDYZBNUQFVRLEY-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  160.21
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  benzyl (2-((S)-3-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)-2,6-dioxopiperidin-1-yl)acetyl)glycinate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以97.2%的产率得到(2-((S)-3-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)-2,6-dioxopiperidin-1-yl)acetyl)glycine
  参考文献：
  名称：

  Novel aminopeptidase N (APN/CD13) inhibitors derived from 3-phenylalanyl-N′-substituted-2,6-piperidinedione

  摘要：

  Aminopeptidase N (APN/CD13) over expressed on tumor cells, plays a critical role in tumor invasion, metastasis, and tumor angiogenesis. Here we described the design, synthesis and preliminary activity studies of novel APN inhibitors with 3-phenylalanyl-N '-substituted-2,6-piperidinedione scaffold. The results showed that compound 7c had the most potent inhibitory activity against APN with the IC50 value to 5.00 +/- 3.17 mu M, which could be used as the lead compound in the future for anticancer agent research. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.078
• 作为产物：
  描述：

  、 甘氨酸苄酯对甲苯磺酸盐 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 以0.87 g的产率得到benzyl (2-((S)-3-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)-2,6-dioxopiperidin-1-yl)acetyl)glycinate
  参考文献：
  名称：

  Novel aminopeptidase N (APN/CD13) inhibitors derived from 3-phenylalanyl-N′-substituted-2,6-piperidinedione

  摘要：

  Aminopeptidase N (APN/CD13) over expressed on tumor cells, plays a critical role in tumor invasion, metastasis, and tumor angiogenesis. Here we described the design, synthesis and preliminary activity studies of novel APN inhibitors with 3-phenylalanyl-N '-substituted-2,6-piperidinedione scaffold. The results showed that compound 7c had the most potent inhibitory activity against APN with the IC50 value to 5.00 +/- 3.17 mu M, which could be used as the lead compound in the future for anticancer agent research. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.078