4-氯咪唑并[1,5-a]喹喔啉 | 221025-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 4-氯咪唑并[1,5-a]喹喔啉
• 英文名称: 6-chloroimidazo[1,5-a]quinoxaline
• 英文别名: 4-chloroimidazo[1,5-a]quinoxaline
• CAS: 221025-38-3
• 化学式: C₁₀H₆ClN₃
• mdl: MFCD26936260
• 分子量: 203.631
• InChiKey: UFFBCELPRQKXDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯-N-甲基苯胺 、 4-氯咪唑并[1,5-a]喹喔啉 生成 N-(2-Chlorophenyl)-N-methylimidazo[1,5-a]quinoxalin-4-amine
  参考文献：
  名称：

  Discovery and initial SAR of imidazoquinoxalines as inhibitors of the Src-family kinase p56Lck

  摘要：

  We have identified a novel series of 1,5-imidizoquinoxalines as inhibitors of Lck with excellent potency (IC(50)s less than or equal to 5 nM) as well as good cellular activity against T-cell proliferation (IC(50)s < 1 muM). Structure-activity studies demonstrate the requirement for the core heterocycle in addition to an optimal 2.6-disubstituted aniline group. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00191-9
• 作为产物：
  描述：

  N-(2-fluoroanilino)-1H-imidazole-4-carboxamide 在 sodium hydride 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 48.25h， 生成 4-氯咪唑并[1,5-a]喹喔啉
  参考文献：
  名称：

  咪唑并[1,2- a ]吡嗪，咪唑并[1,5- a ]喹喔啉和吡唑并[1,5- a ]喹喔啉衍生物作为IKK1和IKK2抑制剂

  摘要：

  转录核因子NF-κB在慢性和急性炎症性疾病中起关键作用。在抑制NF-κB的几种不同策略中，IKK抑制剂的开发似乎是制药业考虑的最有效方法之一。在以前的研究中，在一系列咪唑并[1,2- a ]喹喔啉衍生物中突出了两种潜在的IKK2抑制剂。为了增强该活性，我们在此提出基于咪唑并[1,2- a ]吡嗪，咪唑并[1,5- a ]喹喔啉或吡唑并[1,5- a ]喹喔啉的二十一种新化合物的合成。结构。还测试了它们抑制IKK1和IKK2活性的潜力。

  DOI：

  10.1016/j.ejmech.2017.07.021

文献信息

• In vitro and in vivo anti-tumoral activities of imidazo[1,2-a]quinoxaline, imidazo[1,5-a]quinoxaline, and pyrazolo[1,5-a]quinoxaline derivatives
  作者：Georges Moarbess、Carine Deleuze-Masquefa、Vanessa Bonnard、Stéphanie Gayraud-Paniagua、Jean-Rémi Vidal、Françoise Bressolle、Frédéric Pinguet、Pierre-Antoine Bonnet

  DOI：10.1016/j.bmc.2008.05.022

  日期：2008.7.1

  Imidazoquinoxaline and pyrazoloquinoxaline derivatives, analogues of imiquimod, were synthesized, and their in vitro cytotoxic and pharmacodynamic activities were evaluated. In vitro cytotoxicity studies were assessed against melanoma (A375, M4Be, RPMI-7591), colon (LS174T), breast (MCF7), and lymphoma (Raji) human cancer cell lines. In vivo studies were carried out in M4Be xenografted athymic mice. EAPB0103, EAPB0201, EAPB0202, and EAPB0203 showed significant in vitro activities against A375 compared to fotemustine and imiquimod used as references. These compounds were 6-110 and 2-45 times more active than fotemustine and imiquimod, respectively. EAPB0203 bearing phenethyl as substituent at position 1 and methylamine at position 4 showed the highest activity. EAPB0203 has also a more potent cytotoxic activity than imiquimod and fotemustine in M4Be and RPMI-7591 and interesting cytotoxic activity in other tumor cell lines tested. In vivo, EAPB0203 treatment schedules caused a significant decrease in tumor size compared to vehicle control and fotemustine treatments. (c) 2008 Elsevier Ltd. All rights reserved.
• US6235740B1
  申请人：——

  公开号：US6235740B1

  公开（公告）日：2001-05-22
• US6239133B1
  申请人：——

  公开号：US6239133B1

  公开（公告）日：2001-05-29
• Imidazo[1,2-a]pyrazine, Imidazo[1,5-a]quinoxaline and Pyrazolo[1,5-a]quinoxaline derivatives as IKK1 and IKK2 inhibitors
  作者：Cindy Patinote、Nour Bou Karroum、Georges Moarbess、Carine Deleuze-Masquefa、Kamel Hadj-Kaddour、Pierre Cuq、Mona Diab-Assaf、Issam Kassab、Pierre-Antoine Bonnet

  DOI：10.1016/j.ejmech.2017.07.021

  日期：2017.9

  former study, two potential IKK2 inhibitors have been highlighted among a series of imidazo[1,2-a]quinoxaline derivatives. In order to enhance this activity, we present herein the synthesis of twenty-one new compounds based on the imidazo[1,2-a]pyrazine, imidazo[1,5-a]quinoxaline or pyrazolo[1,5-a]quinoxaline structures. Their potential to inhibit IKK1 and IKK2 activities is also tested.

  转录核因子NF-κB在慢性和急性炎症性疾病中起关键作用。在抑制NF-κB的几种不同策略中，IKK抑制剂的开发似乎是制药业考虑的最有效方法之一。在以前的研究中，在一系列咪唑并[1,2- a ]喹喔啉衍生物中突出了两种潜在的IKK2抑制剂。为了增强该活性，我们在此提出基于咪唑并[1,2- a ]吡嗪，咪唑并[1,5- a ]喹喔啉或吡唑并[1,5- a ]喹喔啉的二十一种新化合物的合成。结构。还测试了它们抑制IKK1和IKK2活性的潜力。
• Discovery and initial SAR of imidazoquinoxalines as inhibitors of the Src-family kinase p56Lck
  作者：Ping Chen、Derek Norris、Edwin J. Iwanowicz、Steven H. Spergel、James Lin、Henry H. Gu、Zhongqi Shen、John Wityak、Tai-An Lin、Suhong Pang、Henry F. De Fex、Sidney Pitt、Ding Ren Shen、Arthur M. Doweyko、Donna A. Bassolino、Jacques Y. Roberge、Michael A. Poss、Bang-Chi Chen、Gary L. Schieven、Joel C. Barrish

  DOI：10.1016/s0960-894x(02)00191-9

  日期：2002.5

  We have identified a novel series of 1,5-imidizoquinoxalines as inhibitors of Lck with excellent potency (IC(50)s less than or equal to 5 nM) as well as good cellular activity against T-cell proliferation (IC(50)s < 1 muM). Structure-activity studies demonstrate the requirement for the core heterocycle in addition to an optimal 2.6-disubstituted aniline group. (C) 2002 Published by Elsevier Science Ltd.