1-[(4-Methoxyphenyl)methyl]-5-nitroquinoxalin-2-one | 357637-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-[(4-Methoxyphenyl)methyl]-5-nitroquinoxalin-2-one
• CAS: 357637-47-9
• 化学式: C₁₆H₁₃N₃O₄
• 分子量: 311.297
• InChiKey: CJAXOJHZDJVVPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  87.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(4-Methoxyphenyl)methyl]-5-nitroquinoxalin-2-one 在 三氟甲磺酸 、 sodium hydride 、 三氟乙酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 苯甲醚 为溶剂， 生成 N-(2,6-Dimethylphenyl)-9-nitroimidazo-[1,5-a]quinoxalin-4-amine
  参考文献：
  名称：

  Synthesis and SAR of novel imidazoquinoxaline-Based Lck inhibitors: improvement of cell potency

  摘要：

  A series of anilino(imidazoquinoxaline) analogues bearing solubilizing side chains at the 6- and 7-positions of the fused phenyl ring has been prepared and evaluated for inhibition against Lck enzyme and of T-cell proliferation. Significant improvement of the cellular activity was achieved over the initial lead, compound 2. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00677-7
• 作为产物：
  描述：

  3-硝基邻苯二胺 在 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 1-[(4-Methoxyphenyl)methyl]-5-nitroquinoxalin-2-one
  参考文献：
  名称：

  Reaction of quinoxalin-2-ones with TosMIC reagent: synthesis of imidazo[1,5-a]quinoxalin-4-ones

  摘要：

  Imidazo[1,5-alpha ]quinoxalin-4-ones were prepared in four steps starting from 1,2-phenylenediamines using a new strategy for the construction of the ring system. A key step in this new method involves the reaction of quinoxalin-2-ones with TosMIC (tosylmethyl isocyanide). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00697-9

文献信息

• Reaction of quinoxalin-2-ones with TosMIC reagent: synthesis of imidazo[1,5-a]quinoxalin-4-ones
  作者：Ping Chen、Joel C. Barrish、Edwin Iwanowicz、James Lin、Mark S. Bednarz、Bang-Chi Chen

  DOI：10.1016/s0040-4039(01)00697-9

  日期：2001.6

  Imidazo[1,5-alpha ]quinoxalin-4-ones were prepared in four steps starting from 1,2-phenylenediamines using a new strategy for the construction of the ring system. A key step in this new method involves the reaction of quinoxalin-2-ones with TosMIC (tosylmethyl isocyanide). (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis and SAR of novel imidazoquinoxaline-Based Lck inhibitors: improvement of cell potency
  作者：Ping Chen、Edwin J. Iwanowicz、Derek Norris、Henry H. Gu、James Lin、Robert V. Moquin、Jagabandhu Das、John Wityak、Steven H. Spergel、Henry de Fex、Suhong Pang、Sydney Pitt、Ding Ren Shen、Gary L. Schieven、Joel C. Barrish

  DOI：10.1016/s0960-894x(02)00677-7

  日期：2002.11

  A series of anilino(imidazoquinoxaline) analogues bearing solubilizing side chains at the 6- and 7-positions of the fused phenyl ring has been prepared and evaluated for inhibition against Lck enzyme and of T-cell proliferation. Significant improvement of the cellular activity was achieved over the initial lead, compound 2. (C) 2002 Elsevier Science Ltd. All rights reserved.