6-phenylimidazo[1,2-a]pyrazine | 1614215-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡嗪类
• 英文名称: 6-phenylimidazo[1,2-a]pyrazine
• 英文别名: 6-Phenylimidazo [1,2-a]pyrazin
• CAS: 1614215-41-6
• 化学式: C₁₂H₉N₃
• 分子量: 195.224
• InChiKey: UCCKLPXHRWSBAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 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：

  6-phenylimidazo[1,2-a]pyrazine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-bromo-6-phenylimidazo[1,2-a]pyrazine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 3-(imidazo[1,2-a]pyrazin-3-ylethynyl)-2-methylbenzamides as potent and selective pan-tropomyosin receptor kinase (TRK) inhibitors

  摘要：

  A series of 3-(imidazo[1,2-a]pyrazin-3-ylethynyl)-2-methylbenzamides was designed and synthesized as new tropomyosin receptor kinases (Trks) inhibitors by utilizing a structure-guided optimization strategy. One of the most potent compounds 90 suppressed TrkA/B/C with IC50 values of 2.65, 10.47 and 2.95 nM, respectively. The compound dose-dependently inhibited brain-derived neurotrophic factor (BDNF)-mediated TrkB activation and suppressed migration and invasion of SH-SY5Y-TrkB neuroblastoma cells expressing high level of TrkB. Inhibitor 90 also inhibited the proliferation of SH-SY5Y-TrkB cells with an IC50 value of 58 nM, which was comparable to that of an US FDA recently approved drug LOXO-101. Compound 90 may serve as a new lead compound for further anti-cancer drug discovery. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.06.064
• 作为产物：
  描述：

  1-(2-phenylethynyl)-1H-imidazole-2-carbaldehyde 在 氨 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以76%的产率得到6-phenylimidazo[1,2-a]pyrazine
  参考文献：
  名称：

  探索1-炔基咪唑的合成用途：区域控制环化成各种咪唑和咪唑

  摘要：

  涉及炔烃的区域控制环化可用于形成各种杂环系统。在这里，我们报告模型1-alkynylimidazoles参与分子内加氢烷氧基化和加氢胺化反应，从而导致各种咪唑并咪唑环系统的参与。在许多情况下，可以通过反应条件的变化来控制对5 -exo-dig或6 -endo-dig环化反应的偏好。这项工作确立了1-炔基咪唑作为多种稠合咪唑杂环的合成中的通用中间体。

  DOI：

  10.1016/j.tet.2014.04.099

文献信息

• Inhibitors of bruton's tyrosine kinase
  申请人：Kondru Rama K.

  公开号：US20100016302A1

  公开（公告）日：2010-01-21

  This application discloses 6-Phenyl-imidazo[1,2-a]pyrazine derivatives according to generic Formulae I-V: wherein, variables Q, R, Y 1 , Y 2 , Y 3 , Y 4 , n, and m are defined as described herein, which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with excessive Btk activity. The compounds are further useful to treat inflammatory and auto immune diseases associated with aberrant B-cell proliferation such as rheumatoid arthritis. Also disclosed are compositions comprising compounds of Formulae I-V and at least one carrier, diluent or excipient.

  该应用程序根据通用公式I-V 揭示了6-苯基咪唑并[1,2-a]吡嗪衍生物： 其中，变量Q、R、Y1、Y2、Y3、Y4、n 和m 如本文所述定义，这些衍生物抑制Btk。本文所披露的化合物可用于调节Btk 的活性并治疗与过度Btk 活性相关的疾病。这些化合物进一步可用于治疗与异常B细胞增殖相关的炎症和自身免疫疾病，如类风湿性关节炎。还披露了包含公式I-V 化合物和至少一种载体、稀释剂或赋形剂的组合物。
• NOVEL PHENYLIMIDAZOPYRAZINES
  申请人：F.Hoffmann-La Roche AG

  公开号：EP2307418A1

  公开（公告）日：2011-04-13
• 新規なフェニルイミダゾピラジン類
  申请人：エフ.ホフマン−ラ ロシュ アーゲー

  公开号：JP5341187B2

  公开（公告）日：2011-11-10
• US8426409B2
  申请人：——

  公开号：US8426409B2

  公开（公告）日：2013-04-23
• [EN] NOVEL PHENYLIMIDAZOPYRAZINES<br/>[FR] NOUVELLES PHÉNYLIMIDAZOPYRAZINES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2010006970A1

  公开（公告）日：2010-01-21

  6-Phenyl-imidazo[l,2-a]pyrazine derivatives according to generic Formulae I-V: wherein variables Q, R, Y1, Y2, Y3, Y4, n, and m are defined as described herein, which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with excessive Btk activity. The compounds are further useful to treat inflammatory and auto immune diseases associated with aberrant B-cell proliferation such as rheumatoid arthritis. Also disclosed are compositions comprising compounds of Formulae I-V and at least one carrier, diluent or excipient.