Acetic acid, 2-(1,3-dihydro-5-methyl-2-oxo-3-indolyl-3,2'-spiro-1,3-dioxane)-, methyl ester | 320741-50-2

• 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: Acetic acid, 2-(1,3-dihydro-5-methyl-2-oxo-3-indolyl-3,2'-spiro-1,3-dioxane)-, methyl ester
• 英文别名: methyl 2-(5'-methyl-2'-oxospiro[1,3-dioxane-2,3'-indole]-1'-yl)acetate
• CAS: 320741-50-2
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: UBCJDYPZSHUKFE-UHFFFAOYSA-N

物化性质

• 沸点：
  529.4±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid, 2-(1,3-dihydro-5-methyl-2-oxo-3-indolyl-3,2'-spiro-1,3-dioxane)-, methyl ester 在 羟胺钾盐 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以64.1%的产率得到N-hydroxy-2-(5'-methyl-2'-oxospiro[1,3-dioxane-2,3'-indole]-1'-yl)acetamide
  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：

  2-hydroxyimino-N-p-tolyl-acetamide 在 硫酸 、 四丁基溴化铵 、 potassium carbonate 、 对甲苯磺酸 、 potassium iodide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 11.5h， 生成 Acetic acid, 2-(1,3-dihydro-5-methyl-2-oxo-3-indolyl-3,2'-spiro-1,3-dioxane)-, methyl ester
  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

文献信息

• Novel indoline-2,3-dione derivatives as inhibitors of aminopeptidase N (APN)
  作者：Kang Jin、Xiaopan Zhang、Chunhua Ma、Yingying Xu、Yumei Yuan、Wenfang Xu

  DOI：10.1016/j.bmc.2012.06.024

  日期：2013.5

  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.