2-amino-8-[(tetrahydropyran-2-yloxy)methyl]-3H-phenoxazin-3-one | 1429632-39-2

• 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: 2-amino-8-[(tetrahydropyran-2-yloxy)methyl]-3H-phenoxazin-3-one
• 英文别名: 2-Amino-8-(oxan-2-yloxymethyl)phenoxazin-3-one；2-amino-8-(oxan-2-yloxymethyl)phenoxazin-3-one
• CAS: 1429632-39-2
• 化学式: C₁₈H₁₈N₂O₄
• 分子量: 326.352
• InChiKey: RGTZUWVBFSPLIR-UHFFFAOYSA-N

物化性质

• 沸点：
  502.9±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-8-[(tetrahydropyran-2-yloxy)methyl]-3H-phenoxazin-3-one 在 盐酸 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 22.0h， 生成 N-[8-(羟基甲基)-3-氧代吩恶嗪-2-基]乙酰胺
  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
• 作为产物：
  描述：

  4-羟基-3-硝基苄醇 在 sodium iodate 、 palladium 10% on activated carbon 、 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 38.17h， 生成 2-amino-8-[(tetrahydropyran-2-yloxy)methyl]-3H-phenoxazin-3-one
  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.