4-(((1r,4r)-4-hydroxycyclohexyl)amino)imidazo[1,2-a]quinoxaline-7-carboxylic acid | 1452864-22-0

• 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: 4-(((1r,4r)-4-hydroxycyclohexyl)amino)imidazo[1,2-a]quinoxaline-7-carboxylic acid
• CAS: 1452864-22-0
• 化学式: C₁₇H₁₈N₄O₃
• 分子量: 326.355
• InChiKey: WFGPBNFFYVTNIS-HAQNSBGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  99.75
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  苄脲 、 4-(((1r,4r)-4-hydroxycyclohexyl)amino)imidazo[1,2-a]quinoxaline-7-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-benzyl-4-(((1r,4r)-4-hydroxycyclohexyl)amino)imidazo[1,2-a]quinoxaline-7-carboxamide
  参考文献：
  名称：

  Hit-to-lead optimization and kinase selectivity of imidazo[1,2-a]quinoxalin-4-amine derived JNK1 inhibitors

  摘要：

  As the result of a rhJNK1 HTS, the imidazo[1,2-a]quinoxaline 1 was identified as a 1.6 mu M rhJNK1 inhibitor. Optimization of this compound lead to AX13587 (rhJNK1 IC50 = 160 nM) which was co-crystallized with JNK1 to identify key molecular interactions. Kinase profiling against 125+ kinases revealed AX13587 was an inhibitor of JNK, MAST3, and MAST4 whereas its methylene homolog AX14373 (native JNK1 IC50 = 47 nM) was a highly specific JNK inhibitor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.087
• 作为产物：
  描述：

  ethyl 1-(4-(methoxycarbonyl)-2-nitrophenyl)-1H-imidazole-2-carboxylate 在 铁粉 、 N,N-二甲基苯胺 、 三乙胺 、 potassium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 13.0h， 生成 4-(((1r,4r)-4-hydroxycyclohexyl)amino)imidazo[1,2-a]quinoxaline-7-carboxylic acid
  参考文献：
  名称：

  Hit-to-lead optimization and kinase selectivity of imidazo[1,2-a]quinoxalin-4-amine derived JNK1 inhibitors

  摘要：

  As the result of a rhJNK1 HTS, the imidazo[1,2-a]quinoxaline 1 was identified as a 1.6 mu M rhJNK1 inhibitor. Optimization of this compound lead to AX13587 (rhJNK1 IC50 = 160 nM) which was co-crystallized with JNK1 to identify key molecular interactions. Kinase profiling against 125+ kinases revealed AX13587 was an inhibitor of JNK, MAST3, and MAST4 whereas its methylene homolog AX14373 (native JNK1 IC50 = 47 nM) was a highly specific JNK inhibitor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.087

文献信息

• Hit-to-lead optimization and kinase selectivity of imidazo[1,2-a]quinoxalin-4-amine derived JNK1 inhibitors
  作者：Bei Li、Oana M. Cociorva、Tyzoon Nomanbhoy、Helge Weissig、Qiang Li、Kai Nakamura、Marek Liyanage、Melissa C. Zhang、Ann Y. Shih、Arwin Aban、Yi Hu、Julia Cajica、Lan Pham、John W. Kozarich、Kevin R. Shreder

  DOI：10.1016/j.bmcl.2013.06.087

  日期：2013.9

  As the result of a rhJNK1 HTS, the imidazo[1,2-a]quinoxaline 1 was identified as a 1.6 mu M rhJNK1 inhibitor. Optimization of this compound lead to AX13587 (rhJNK1 IC50 = 160 nM) which was co-crystallized with JNK1 to identify key molecular interactions. Kinase profiling against 125+ kinases revealed AX13587 was an inhibitor of JNK, MAST3, and MAST4 whereas its methylene homolog AX14373 (native JNK1 IC50 = 47 nM) was a highly specific JNK inhibitor. (C) 2013 Elsevier Ltd. All rights reserved.