7-bromo-2-(2-chlorophenyl)-N,N-dimethyl-3H-imidazo[4,5-c]quinolin-4-amine | 1428442-97-0

• 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: 7-bromo-2-(2-chlorophenyl)-N,N-dimethyl-3H-imidazo[4,5-c]quinolin-4-amine
• CAS: 1428442-97-0
• 化学式: C₁₈H₁₄BrClN₄
• 分子量: 401.693
• InChiKey: LFPFNTSUIHOZFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  HCl 、 二甲胺 以 四氢呋喃 为溶剂， 反应 0.5h， 以99%的产率得到7-bromo-2-(2-chlorophenyl)-N,N-dimethyl-3H-imidazo[4,5-c]quinolin-4-amine
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted imidazoquinoline derivatives as mPGES-1 inhibitors

  摘要：

  We have Previously reported 7-bromo-2-(2-chrolophenyl)-imidazoquinolin-4(5H)-one (1) as a novel potent mPGES-1 inhibitor. To clarify the essential functional groups of 1 for inhibition of mPGES-1, we investigated this compound structure-activity relationship following substitution at the C(4)-position and N-alkylation at the N(1)-, the N(3)-, and the N(5)-positions of I. To prepare the target compounds, we established a good methodology for selective N-alkylation of the imidazoquinolin-4-one, that is, selective alkylation of 1 at the N(3)- and N(5)-positions was achieved by use of an appropriate base and introduction of a protecting group at the nitrogen atom in the imidazole part, respectively. Replacement of the C(4)-oxo group with nitrogen- or sulfur- linked substituents gave decreased inhibitory activity for mPGES-1, and introduction of alkyl groups on the nitrogen atom at the N(1)-, the N(3)-, and the N(5)-positions resulted in even larger loss of inhibitory activity. These results revealed that the C(4)-oxo group, and the hydrogen atoms at the N(5)-position and the imidazole part were the best substituents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.018

文献信息

• Synthesis and biological evaluation of substituted imidazoquinoline derivatives as mPGES-1 inhibitors
  作者：Tomoya Shiro、Keisuke Kakiguchi、Hirotada Takahashi、Hidetaka Nagata、Masanori Tobe

  DOI：10.1016/j.bmc.2013.01.018

  日期：2013.4

  We have Previously reported 7-bromo-2-(2-chrolophenyl)-imidazoquinolin-4(5H)-one (1) as a novel potent mPGES-1 inhibitor. To clarify the essential functional groups of 1 for inhibition of mPGES-1, we investigated this compound structure-activity relationship following substitution at the C(4)-position and N-alkylation at the N(1)-, the N(3)-, and the N(5)-positions of I. To prepare the target compounds, we established a good methodology for selective N-alkylation of the imidazoquinolin-4-one, that is, selective alkylation of 1 at the N(3)- and N(5)-positions was achieved by use of an appropriate base and introduction of a protecting group at the nitrogen atom in the imidazole part, respectively. Replacement of the C(4)-oxo group with nitrogen- or sulfur- linked substituents gave decreased inhibitory activity for mPGES-1, and introduction of alkyl groups on the nitrogen atom at the N(1)-, the N(3)-, and the N(5)-positions resulted in even larger loss of inhibitory activity. These results revealed that the C(4)-oxo group, and the hydrogen atoms at the N(5)-position and the imidazole part were the best substituents. (C) 2013 Elsevier Ltd. All rights reserved.