2-(7-bromo-3H-imidazo[4,5-c]quinolin-2-yl)benzonitrile | 1355478-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(7-bromo-3H-imidazo[4,5-c]quinolin-2-yl)benzonitrile
• CAS: 1355478-10-2
• 化学式: C₁₇H₉BrN₄
• 分子量: 349.189
• InChiKey: PHJMVHOGZUBLSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-溴-4-氯-3-硝基喹啉 在 sodium pyrosulfate 、 氨 、 铁粉 、 氯化铵 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.0h， 生成 2-(7-bromo-3H-imidazo[4,5-c]quinolin-2-yl)benzonitrile
  参考文献：
  名称：

  Synthesis and SAR study of imidazoquinolines as a novel structural class of microsomal prostaglandin E2 synthase-1 inhibitors

  摘要：

  The imidazoquinoline derivative 1 was found as a novel mPGES-1 inhibitor. Optimization of 1 led to the identification of the 2-chlorophenyl group at the C(2)-position and the quinolone structure at the C(4)-position. Compound 33, the most potent synthesized compound, showed excellent mPGES-1 inhibition (IC50 = 9.1 nM) with high selectivity (>1000-fold) over both COX-1 and COX-2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.015

文献信息

• Synthesis and SAR study of imidazoquinolines as a novel structural class of microsomal prostaglandin E2 synthase-1 inhibitors
  作者：Tomoya Shiro、Hirotada Takahashi、Keisuke Kakiguchi、Yoshifumi Inoue、Keiki Masuda、Hidetaka Nagata、Masanori Tobe

  DOI：10.1016/j.bmcl.2011.11.015

  日期：2012.1

  The imidazoquinoline derivative 1 was found as a novel mPGES-1 inhibitor. Optimization of 1 led to the identification of the 2-chlorophenyl group at the C(2)-position and the quinolone structure at the C(4)-position. Compound 33, the most potent synthesized compound, showed excellent mPGES-1 inhibition (IC50 = 9.1 nM) with high selectivity (>1000-fold) over both COX-1 and COX-2. (C) 2011 Elsevier Ltd. All rights reserved.