5-(2,6-dichloro-3-nitrobenzyloxy)isoquinoline | 206882-37-3

• 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-(2,6-dichloro-3-nitrobenzyloxy)isoquinoline
• 英文别名: 5-[(2,6-Dichloro-3-nitrophenyl)methoxy]isoquinoline
• CAS: 206882-37-3
• 化学式: C₁₆H₁₀Cl₂N₂O₃
• 分子量: 349.173
• InChiKey: QSMAJKFOFOXXHD-UHFFFAOYSA-N

物化性质

• 沸点：
  538.7±45.0 °C(Predicted)
• 密度：
  1.471±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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-acetamido-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
• 作为产物：
  描述：

  2,6‐dichloro‐3‐nitrobenzyl methanesulfonate 、 5-羟基异喹啉 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到5-(2,6-dichloro-3-nitrobenzyloxy)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

文献信息

• Discovery of a novel benzyloxyisoquinoline derivative with potent anti-Helicobacter pylori activity
  作者：Yoshiki Yoshida、David Barrett、Hidenori Azami、Chizu Morinaga、Yoshimi Matsumoto、Hisashi Takasugi

  DOI：10.1016/s0960-894x(98)00335-7

  日期：1998.7

  The synthesis and in vitro optimization of the anti-Helicobacter pylori activity of a novel series of benzyloxyisoquinoline derivatives discovered by a random screening process, are described. FR180102 (7f), having a 3-acetamido-2,6-dichlorobenzyl moiety, was found to have extremely potent activity against H. pylori and no effect against a series of common Gram-positive and Gram-negative bacteria.

  描述了通过随机筛选方法发现的一系列新的苄氧基异喹啉衍生物的抗幽门螺杆菌活性的合成和体外优化。发现具有3-乙酰氨基-2，6-二氯苄基部分的FR180102（7f）对幽门螺杆菌具有极强的活性，对一系列常见的革兰氏阳性和革兰氏阴性细菌没有作用。
• JPH1087629A
  申请人：——

  公开号：JPH1087629A

  公开（公告）日：1998-04-07
• Studies on Anti-Helicobacter pylori Agents. Part 1: Benzyloxyisoquinoline Derivatives
  作者：Yoshiki Yoshida、David Barrett、Hidenori Azami、Chizu Morinaga、Satoru Matsumoto、Yoshimi Matsumoto、Hisashi Takasugi

  DOI：10.1016/s0968-0896(99)00203-5

  日期：1999.11

  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.