5'-methylspiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one | 853751-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5'-methylspiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one
• 英文别名: 5'-methylspiro[1,3-dioxane-2,3'-1H-indole]-2'-one
• CAS: 853751-57-2
• 化学式: C₁₂H₁₃NO₃
• mdl: MFCD00617568
• 分子量: 219.24
• InChiKey: TVTLYVBDOGQTAV-UHFFFAOYSA-N

物化性质

• 溶解度：
  >32.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5'-methylspiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one 在 羟胺钾盐 、 四丁基溴化铵 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 7.5h， 生成 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 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 5.5h， 生成 5'-methylspiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one
  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

• Pyrimidoindolones and methods for using same
  申请人：Dollings Jeffrey Paul

  公开号：US20050250798A1

  公开（公告）日：2005-11-10

  Novel pyrimidoindolone compounds are disclosed. Methods of using the pyrimidoindolone compounds and compositions containing the compounds in the treatment and/or prevention of disease and other conditions related to inflammation, neurodegeneration, osteoarthritis and apoptosis are also disclosed.

  揭示了一种新型的嘧啶吲哚酮化合物。还揭示了使用这些嘧啶吲哚酮化合物的方法，以及包含这些化合物的组合物在治疗和/或预防与炎症、神经退行性疾病、骨关节炎和细胞凋亡相关的疾病和其他情况中的应用。
• PYRIMIDOINDOLONES AND METHODS FOR USING SAME
  申请人：Dollings Jeffrey Paul

  公开号：US20070270587A1

  公开（公告）日：2007-11-22

  Novel pyrimidoindolone compounds are disclosed. Methods of using the pyrimidoindolone compounds and compositions containing the compounds in the treatment and/or prevention of disease and other conditions related to inflammation, neurodegeneration, osteoarthritis and apoptosis are also disclosed.

  本发明揭示了新型嘧啶并吲哚酮类化合物。还揭示了使用这些嘧啶并吲哚酮类化合物和含有这些化合物的组合物在治疗和/或预防与炎症、神经退行性、骨关节炎和细胞凋亡等疾病和其他相关病症方面的方法。
• Synthesis of heteroaromatic N-β-glycosides of N-acetylglucosamine under phase transfer conditions: II. Indolin-2-one glycosaminides
  作者：V. O. Kur’yanov、T. A. Chupakhina、O. V. Shishkin、S. V. Shishkina、V. Ya. Chirva

  DOI：10.1134/s1068162008060137

  日期：2008.11

  Regioselective N-beta-glucosamination of various unsubstituted or C4-, C5-, or C6-monosubstituted indolin-2-ones under phase transfer conditions was studied. The regioselectivity was unambiguously proved by H-1 NMR spectroscopy and X-ray analysis. The presence of substituent at C7 of the aromatic ring leads to the formation of either a mixture of isomeric N-beta- and O-beta-D-glucosaminides, or only oxazoline and/or 2-acetamidoglycal irrespective of the reaction conditions.
• US7256198B2
  申请人：——

  公开号：US7256198B2

  公开（公告）日：2007-08-14