2-Amino-8-methylphenoxazin-3-one | 1429632-36-9

• 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-methylphenoxazin-3-one
• 英文别名: 2-amino-8-methylphenoxazin-3-one
• CAS: 1429632-36-9
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: YGECNMSWFYYIDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  64.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基苯酚 、 邻氨基对甲苯酚 在 sodium iodate 作用下， 以 水 、 丙酮 为溶剂， 反应 20.17h， 以35%的产率得到2-Amino-8-methylphenoxazin-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

• Phenoxazinone synthase-like catalytic activity of novel mono- and tetranuclear copper(<scp>ii</scp>) complexes with 2-benzylaminoethanol
  作者：Oksana V. Nesterova、Olena E. Bondarenko、Armando J. L. Pombeiro、Dmytro S. Nesterov

  DOI：10.1039/d0dt00222d

  日期：——

  compounds act as catalysts for the aerobic oxidation of o-aminophenol to the phenoxazinone chromophore (phenoxazinone synthase-like activity), with the maximum reaction rates of 4.0 × 10−7, 2.5 × 10−7 and 2.1 × 10−7 M s−1 for 1, 2 and 3, respectively, supported by the quantitative yield of the product after 24 h. The dependence of the reaction rates on catalyst concentrations is evidence of reaction orders

  三种新型配位化合物[Cu（ca）2（Hbae）2 ]（1），[Cu（va）2（Hbae）2 ]（2）和[Cu 4（va）4（bae）4 ]·H 2 O（3）是通过氯化铜（II）（1和2）或四氟硼酸盐（3）与CH 3 OH（1和3）或CH 3 CN（2）2-苄基氨基乙醇的自组装反应制备的。（Hbae）和肉桂酸（Hca，1）或戊酸（Hva，2和3）酸。晶体学分析表明1和2均具有单核晶体结构，其中复合分子是H键形成延伸的超分子链。的四核结构3是根据的Cu 4（μ 3 -O）4 }芯，其中，所述金属原子被μ结合在一起3个氧桥由2-苄基氨基乙醇形成整体立方烷状构造。1-3中的强氢键导致相邻分子连接成一维链。浓度依赖的ESI-MS研究揭示了在1–3溶液中二核，三核和四核物种之间的平衡。所有三种化合物作为催化剂用于的有氧氧化Ò氨基苯酚至phenoxazinone发色团（phenoxazinone合酶样活性），具有4
• 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.