5-(3-acetylmethylacetamido-2,6-dichlorobenzyloxy)isoquinoline | 206884-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5-(3-acetylmethylacetamido-2,6-dichlorobenzyloxy)isoquinoline
• 英文别名: N-[2,4-dichloro-3-(isoquinolin-5-yloxymethyl)phenyl]-3-oxobutanamide
• CAS: 206884-32-4
• 化学式: C₂₀H₁₆Cl₂N₂O₃
• 分子量: 403.265
• InChiKey: MGNYVOVBJBNTND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲氧基胺盐酸盐 、 5-(3-acetylmethylacetamido-2,6-dichlorobenzyloxy)isoquinoline 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以69%的产率得到5-{2,6-dichloro-3-(3-methoxyimino-1-butanoylamino)benzyloxy}isoquinoline
  参考文献：
  名称：

  Studies on Anti-Helicobacter pylori Agents. Part 1: Benzyloxyisoquinoline Derivatives

  摘要：

  The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of benzyloxyisoquinoline derivatives that was discovered by a random screening process, are described. In the in vitro assay, compound 10c containing a 3-acetamido-2,6-dichlorobenzyl substituent was found to have extremely potent activity against H. pylori and no activity against other common bacteria. The anti-H. pylori activity of 10c was superior to that of amoxicillin (AMPC) (1) and clarithromycin (CAM) (2), However, 10c did not show in vivo efficacy in a mouse infection model; a feature attributed to the lack of strong bactericidal activity at short contact times. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00203-5
• 作为产物：
  描述：

  5-(2,6-dichloro-3-nitrobenzyloxy)isoquinoline 在 三氯化铁 、 一水合肼 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 生成 5-(3-acetylmethylacetamido-2,6-dichlorobenzyloxy)isoquinoline
  参考文献：
  名称：

  Studies on Anti-Helicobacter pylori Agents. Part 1: Benzyloxyisoquinoline Derivatives

  摘要：

  The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of benzyloxyisoquinoline derivatives that was discovered by a random screening process, are described. In the in vitro assay, compound 10c containing a 3-acetamido-2,6-dichlorobenzyl substituent was found to have extremely potent activity against H. pylori and no activity against other common bacteria. The anti-H. pylori activity of 10c was superior to that of amoxicillin (AMPC) (1) and clarithromycin (CAM) (2), However, 10c did not show in vivo efficacy in a mouse infection model; a feature attributed to the lack of strong bactericidal activity at short contact times. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00203-5