7,8-Dimethoxy-5H-imidazo[1,5-a]quinoxalin-4-one | 221068-29-7

• 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: 7,8-Dimethoxy-5H-imidazo[1,5-a]quinoxalin-4-one
• CAS: 221068-29-7
• 化学式: C₁₂H₁₁N₃O₃
• mdl: MFCD27414834
• 分子量: 245.238
• InChiKey: IZMUQGJWBDCVJO-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C
• 沸点：
  356.1±42.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7,8-Dimethoxy-5H-imidazo[1,5-a]quinoxalin-4-one 在 三溴化硼 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 N-(2-Chloro-6-methylphenyl)[1,3]dioxolo[4,5-g]imidazo[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：

  1,2-二氨基-4,5-二甲氧基苯 在 三氟甲磺酸 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 苯甲醚 、 甲苯 为溶剂， 生成 7,8-Dimethoxy-5H-imidazo[1,5-a]quinoxalin-4-one
  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

文献信息

• A New Strategy for the Construction of the Imidazo[1,5-<i>a</i>]quinoxalin-4-one Ring System and Its Application to the Efficient Synthesis of BMS-238497, a Novel and Potent Lck Inhibitor
  作者：Bang-Chi Chen、Rulin Zhao、Mark S. Bednarz、Bei Wang、Joseph E. Sundeen、Joel C. Barrish

  DOI：10.1021/jo0355348

  日期：2004.2.1

  ring system. The new method involves condensation of o-nitroaniline with glyoxylate in methanol followed by treatment of the resulting α-(o-nitroanilino)-α-methoxy acetate with tosylmethyl isocyanide (TosMIC) reagent to give 1-(o-nitrophenyl)imidazole-5-carboxylate. Reductive cyclization of the nitro imidazole carboxylate afforded imidazo[1,5-a]quinoxalin-4-one in three steps and 60% overall yield. The

  为构建咪唑并[1,5 - a ]喹喔啉-4-一环系统开发了一种新的有效策略。新方法涉及将邻硝基苯胺与乙醛酸酯在甲醇中缩合，然后用甲苯磺酰基甲基异氰化物（TosMIC）试剂处理所得的α-（邻硝基苯胺基）-α-甲氧基乙酸酯，得到1-（邻硝基苯基）咪唑-5 -羧酸盐。硝基咪唑羧酸盐的还原环化以三个步骤提供咪唑并[1,5 - a ]喹喔啉-4-酮，总产率为60％。该新方法已成功应用于合成新型有效的Lck抑制剂BMS-238497。
• 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.
• US6235740B1
  申请人：——

  公开号：US6235740B1

  公开（公告）日：2001-05-22
• 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.