HCl | 1355478-15-7

• 英文名称: HCl
• CAS: 1355478-15-7
• 化学式: C₁₆H₈BrCl₂N₃
• 分子量: 393.07
• InChiKey: QMUQOBMTBNHEBK-UHFFFAOYSA-N

物化性质

• 沸点：
  595.2±60.0 °C(Predicted)
• 密度：
  1.725±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.57
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  HCl 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 以89%的产率得到7-bromo-2-(2-chlorophenyl)imidazo[4,5-c]quinolin-4(5H)-one
  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
• 作为产物：
  描述：

  7-溴喹啉-3,4-二胺 在 sodium pyrosulfate 、 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 HCl
  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 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.