O-5-isoquinolyl dimethylthiocarbamate | 258842-77-2

• 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: O-5-isoquinolyl dimethylthiocarbamate
• 英文别名: 5-(N,N-dimethylthiocarbamate)-O-isoquinoline；O-isoquinolin-5-yl N,N-dimethylcarbamothioate
• CAS: 258842-77-2
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: KKSTZQYWULNPJW-UHFFFAOYSA-N

物化性质

• 沸点：
  360.337±34.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.249±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-5-isoquinolyl dimethylthiocarbamate 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 5-(3-acetamido-2,6-dichlorobenzylthio)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：

  二甲氨基硫代甲酰氯 、 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76%的产率得到O-5-isoquinolyl dimethylthiocarbamate
  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

• WO2006/103120
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.