2-(2-chlorophenyl)-7-(n-pentyl)imidazo[4,5-c]quinolin-4(5H)-one | 1436688-28-6

• 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-(2-chlorophenyl)-7-(n-pentyl)imidazo[4,5-c]quinolin-4(5H)-one
• 英文别名: 2-(2-Chlorophenyl)-7-pentyl-3,5-dihydroimidazo[4,5-c]quinolin-4-one；2-(2-chlorophenyl)-7-pentyl-3,5-dihydroimidazo[4,5-c]quinolin-4-one
• CAS: 1436688-28-6
• 化学式: C₂₁H₂₀ClN₃O
• 分子量: 365.862
• InChiKey: JULNGCZCLLQCAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  7-bromo-2-(2-chlorophenyl)imidazo[4,5-c]quinolin-4(5H)-one 、 戊基溴化锌 在 二(三叔丁基膦)钯 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 0.5h， 以57%的产率得到2-(2-chlorophenyl)-7-(n-pentyl)imidazo[4,5-c]quinolin-4(5H)-one
  参考文献：
  名称：

  7-Phenyl-imidazoquinolin-4(5H)-one derivatives as selective and orally available mPGES-1 inhibitors

  摘要：

  To identify compounds with strong mPGES-1 inhibitory activity and clear in vitro ADME profile, we optimized the lead compound 1 by carrying our substitutions at the C(7)-and C(8)-positions. Replacement of the bromine atom of 1 with various substituents led to identification of the phenyl group as the best C(7)-substituent giving strong inhibitory activity with good in vitro ADME profile. Further SAR examination on both the C(2)-and the C(7)-phenyl groups provided compound 39 as the best candidate for further development. Compound 39 exhibited strong mPGES-1 inhibitory activity (IC50 = 4.1 nM), potent cell-based functional activity (IC50 = 33 nM) with good mPGES-1 selectivity (over 700-fold), excellent in vitro ADME profile, and good oral absorption in rat PK study. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.069

文献信息

• 7-Phenyl-imidazoquinolin-4(5H)-one derivatives as selective and orally available mPGES-1 inhibitors
  作者：Tomoya Shiro、Keisuke Kakiguchi、Hirotada Takahashi、Hidetaka Nagata、Masanori Tobe

  DOI：10.1016/j.bmc.2013.03.069

  日期：2013.6

  To identify compounds with strong mPGES-1 inhibitory activity and clear in vitro ADME profile, we optimized the lead compound 1 by carrying our substitutions at the C(7)-and C(8)-positions. Replacement of the bromine atom of 1 with various substituents led to identification of the phenyl group as the best C(7)-substituent giving strong inhibitory activity with good in vitro ADME profile. Further SAR examination on both the C(2)-and the C(7)-phenyl groups provided compound 39 as the best candidate for further development. Compound 39 exhibited strong mPGES-1 inhibitory activity (IC50 = 4.1 nM), potent cell-based functional activity (IC50 = 33 nM) with good mPGES-1 selectivity (over 700-fold), excellent in vitro ADME profile, and good oral absorption in rat PK study. (C) 2013 Elsevier Ltd. All rights reserved.