methyl 2-amino-8-(hydroxymethyl)-3-oxo-3H-phenoxazine-1-carboxylate | 1429632-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: methyl 2-amino-8-(hydroxymethyl)-3-oxo-3H-phenoxazine-1-carboxylate
• 英文别名: Methyl 2-amino-8-(hydroxymethyl)-3-oxophenoxazine-1-carboxylate；methyl 2-amino-8-(hydroxymethyl)-3-oxophenoxazine-1-carboxylate
• CAS: 1429632-42-7
• 化学式: C₁₅H₁₂N₂O₅
• 分子量: 300.271
• InChiKey: GDIUIESEBJVCEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-羟基-2-硝基苯甲酸 在 盐酸 、 sodium iodate 、 palladium 10% on activated carbon 、 氢气 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 30.17h， 生成 methyl 2-amino-8-(hydroxymethyl)-3-oxo-3H-phenoxazine-1-carboxylate
  参考文献：
  名称：

  Aminophenoxazinones as Inhibitors of Indoleamine 2,3-Dioxygenase (IDO). Synthesis of Exfoliazone and Chandrananimycin A

  摘要：

  A range of 2-aminophenoxazin-3-ones has been prepared by oxidative cyclocondensation of 2-aminophenols, including the natural products exfoliazone and chandrananimycin A, both synthesized for the first time. The compounds were evaluated for their ability to inhibit indoleamine 2,3-dioxygenase. Compounds containing additional electron-withdrawing carboxylate groups, such as cinnabarinic acid, showed modest inhibitory activity with a dose response.

  DOI：

  10.1021/jm400049z

文献信息

• Aminophenoxazinones as Inhibitors of Indoleamine 2,3-Dioxygenase (IDO). Synthesis of Exfoliazone and Chandrananimycin A
  作者：Raffaele Pasceri、David Siegel、David Ross、Christopher J. Moody

  DOI：10.1021/jm400049z

  日期：2013.4.25

  A range of 2-aminophenoxazin-3-ones has been prepared by oxidative cyclocondensation of 2-aminophenols, including the natural products exfoliazone and chandrananimycin A, both synthesized for the first time. The compounds were evaluated for their ability to inhibit indoleamine 2,3-dioxygenase. Compounds containing additional electron-withdrawing carboxylate groups, such as cinnabarinic acid, showed modest inhibitory activity with a dose response.