7-methoxy-5H-imidazo[1,5-a]quinoxalin-4-one | 357637-61-7

• 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: 7-methoxy-5H-imidazo[1,5-a]quinoxalin-4-one
• CAS: 357637-61-7
• 化学式: C₁₁H₉N₃O₂
• 分子量: 215.211
• InChiKey: WVCWCBKPFSLVIY-UHFFFAOYSA-N

物化性质

• 沸点：
  325.0±35.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-methoxy-5H-imidazo[1,5-a]quinoxalin-4-one 在 硝酸铵 、 硫酸 、 吡啶盐酸盐 、 三氯氧磷 作用下， 以 戊醇 为溶剂， 生成
  参考文献：
  名称：

  咪唑并[1,5- a ]喹喔啉类药物是不可逆的BTK抑制剂，用于治疗类风湿关节炎

  摘要：

  合成了咪唑并[1,5- a ]喹喔啉，它们起不可逆的布鲁顿酪氨酸激酶（BTK）抑制剂的作用。介绍了该系列化合物的合成和SAR以及与ITK酶的守门员变体复合的前导化合物36的X射线晶体结构。铅化合物在临床前RA模型中显示出良好的体内功效。

  DOI：

  10.1016/j.bmcl.2011.09.008
• 作为产物：
  描述：

  7-methoxy-3,4-dihydro-1H-quinoxalin-2-one 在 sodium hydroxide 、 三氟甲磺酸 、 双氧水 、 sodium hydride 、 苯甲醚 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 7-methoxy-5H-imidazo[1,5-a]quinoxalin-4-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

• 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.
• A Van Leusen deprotection-cyclization strategy as a fast entry into two imidazoquinoxaline families
  作者：Fabio De Moliner、Christopher Hulme

  DOI：10.1016/j.tetlet.2012.08.072

  日期：2012.10

  A concise synthesis of two pharmacologically relevant classes of molecules possessing the imidazoquinoxaline core is reported. The protocol involves use of 1,2-phenylenediamines and glyoxylic acid derivatives, namely ethyl glyoxylate or benzylglyoxamide, along with tosylmethylisocyanides in a microwave-assisted Van Leusen three-component condensation. Subsequent unmasking (Boc removal) of an internal amino-nucleophile promotes deprotection and cyclization that take place either spontaneously in a one-pot fashion to give 8 or upon acidic treatment under microwave irradiation after isolation of the imidazole intermediate to give 11. Of note, a tricyclic framework is hence assembled by means of a rapid and straightforward method with a high bond-forming efficiency. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.
• Imidazo[1,5-a]quinoxalines as irreversible BTK inhibitors for the treatment of rheumatoid arthritis
  作者：Kyung-Hee Kim、Andreas Maderna、Mark E. Schnute、Martin Hegen、Shashi Mohan、Joy Miyashiro、Laura Lin、Evelyn Li、Sean Keegan、Jennifer Lussier、Christopher Wrocklage、Cheryl L. Nickerson-Nutter、Arthur J. Wittwer、Holly Soutter、Nicole Caspers、Seungil Han、Ravi Kurumbail、Kyri Dunussi-Joannopoulos、John Douhan、Allan Wissner

  DOI：10.1016/j.bmcl.2011.09.008

  日期：2011.11

  Imidazo[1,5-a]quinoxalines were synthesized that function as irreversible Bruton’s tyrosine kinase (BTK) inhibitors. The syntheses and SAR of this series of compounds are presented as well as the X-ray crystal structure of the lead compound 36 in complex with a gate-keeper variant of ITK enzyme. The lead compound showed good in vivo efficacy in preclinical RA models.

  合成了咪唑并[1,5- a ]喹喔啉，它们起不可逆的布鲁顿酪氨酸激酶（BTK）抑制剂的作用。介绍了该系列化合物的合成和SAR以及与ITK酶的守门员变体复合的前导化合物36的X射线晶体结构。铅化合物在临床前RA模型中显示出良好的体内功效。