methyl (2-(5-bromo-2-oxospiro[indoline-3,2'-[1,3]dioxolan]-1-yl)acetyl)-L-valinate | 1446416-51-8

• 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: methyl (2-(5-bromo-2-oxospiro[indoline-3,2'-[1,3]dioxolan]-1-yl)acetyl)-L-valinate
• CAS: 1446416-51-8
• 化学式: C₁₈H₂₁BrN₂O₆
• 分子量: 441.279
• InChiKey: IWVPGDUZADOVCW-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (2-(5-bromo-2-oxospiro[indoline-3,2'-[1,3]dioxolan]-1-yl)acetyl)-L-valinate 在 羟胺钾盐 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以48.4%的产率得到2-(2-(5'-bromo-2'-oxospiro[[1,3]dioxolane-2,3'-indoline]-1'-yl)acetamido)-N-hydroxy-3-methylbutanamide
  参考文献：
  名称：

  Novel indoline-2,3-dione derivatives as inhibitors of aminopeptidase N (APN)

  摘要：

  Aminopeptidase N (APN/CD13), as a zinc-containing ectoenzyme, plays a critical role in the process of tumor angiogenesis, invasion and metastasis. Through the docking-based virtual screening of chemical databases and the further activity assay, we discovered that compound 10c exhibits potent and selective inhibitory ability towards APN. In addition, a series of indoline-2,3-dione derivates have been designed and synthesized as APN inhibitors. The results of preliminary activity evaluation showed that compound 12a (IC50 = 0.074 +/- 0.0026 mu M) exhibited the best inhibitory activity against APN, which could be used for further anticancer agent research. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.06.024
• 作为产物：
  描述：

  4-溴苯胺 在 N-甲基吗啉 、 盐酸 、 硫酸 、 盐酸羟胺 、 四丁基溴化铵 、 potassium carbonate 、 对甲苯磺酸 、 sodium sulfate 、 potassium iodide 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 27.0h， 生成 methyl (2-(5-bromo-2-oxospiro[indoline-3,2'-[1,3]dioxolan]-1-yl)acetyl)-L-valinate
  参考文献：
  名称：

  Novel indoline-2,3-dione derivatives as inhibitors of aminopeptidase N (APN)

  摘要：

  Aminopeptidase N (APN/CD13), as a zinc-containing ectoenzyme, plays a critical role in the process of tumor angiogenesis, invasion and metastasis. Through the docking-based virtual screening of chemical databases and the further activity assay, we discovered that compound 10c exhibits potent and selective inhibitory ability towards APN. In addition, a series of indoline-2,3-dione derivates have been designed and synthesized as APN inhibitors. The results of preliminary activity evaluation showed that compound 12a (IC50 = 0.074 +/- 0.0026 mu M) exhibited the best inhibitory activity against APN, which could be used for further anticancer agent research. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.06.024