(3R,4R)-methyl 1-(2-(3-(diisopropoxyphosphoryl)thiophen-2-ylthio)ethyl)-4-(3-hydroxy-3-(6-methoxyquinolin-4-yl)propyl)piperidine-3-carboxylate

• 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: (3R,4R)-methyl 1-(2-(3-(diisopropoxyphosphoryl)thiophen-2-ylthio)ethyl)-4-(3-hydroxy-3-(6-methoxyquinolin-4-yl)propyl)piperidine-3-carboxylate
• 英文别名: methyl (3R,4R)-1-[2-[3-di(propan-2-yloxy)phosphorylthiophen-2-yl]sulfanylethyl]-4-[3-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate
• 化学式: C₃₂H₄₅N₂O₇PS₂
• 分子量: 664.824
• InChiKey: UBBLJWZODGRWNO-NANLIHLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (3R,4R)-methyl 1-(2-(3-(diisopropoxyphosphoryl)thiophen-2-ylthio)ethyl)-4-(3-hydroxy-3-(6-methoxyquinolin-4-yl)propyl)piperidine-3-carboxylate 在 lithium hydroxide monohydrate 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 (3R,4R)-1-(2-(3-(diisopropoxyphosphoryl)thiophen-2-ylthio)ethyl)-4-((S)-3-hydroxy-3-(6-methoxyquinolin-4-yl)propyl)piperidine-3-carboxylic acid 、 (3R,4R)-1-(2-(3-(diisopropoxyphosphoryl)thiophen-2-ylthio)ethyl)-4-((R)-3-hydroxy-3-(6-methoxyquinolin-4-yl)propyl)piperidine-3-carboxylic acid
  参考文献：
  名称：

  Selenophene-Containing Inhibitors of Type IIA Bacterial Topoisomerases

  摘要：

  We investigated compounds related to the previously reported anti-staphyloccocal agent AVE6971 in an effort to attenuate inhibition of hERG potassium channel current that has been noted for this and related antibacterial drug classes. While most modifications of the original thiophene group compromised antibacterial activity, one selenophene analogue displayed (i) improved activity against the primary target enzyme DNA gyrase, (ii) similar activities against a panel of MRSA clinical isolates, and (iii) reduced hERG channel inhibition.

  DOI：

  10.1021/jm2002124
• 作为产物：
  描述：

  氯磷酸二异丙酯 在 sodium tetrahydroborate 、 sodium hydride 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 (3R,4R)-methyl 1-(2-(3-(diisopropoxyphosphoryl)thiophen-2-ylthio)ethyl)-4-(3-hydroxy-3-(6-methoxyquinolin-4-yl)propyl)piperidine-3-carboxylate
  参考文献：
  名称：

  Selenophene-Containing Inhibitors of Type IIA Bacterial Topoisomerases

  摘要：

  We investigated compounds related to the previously reported anti-staphyloccocal agent AVE6971 in an effort to attenuate inhibition of hERG potassium channel current that has been noted for this and related antibacterial drug classes. While most modifications of the original thiophene group compromised antibacterial activity, one selenophene analogue displayed (i) improved activity against the primary target enzyme DNA gyrase, (ii) similar activities against a panel of MRSA clinical isolates, and (iii) reduced hERG channel inhibition.

  DOI：

  10.1021/jm2002124

文献信息

• Selenophene-Containing Inhibitors of Type IIA Bacterial Topoisomerases
  作者：Jason A. Wiles、Avinash S. Phadke、Barton J. Bradbury、Michael J. Pucci、Jane A. Thanassi、Milind Deshpande

  DOI：10.1021/jm2002124

  日期：2011.5.12

  We investigated compounds related to the previously reported anti-staphyloccocal agent AVE6971 in an effort to attenuate inhibition of hERG potassium channel current that has been noted for this and related antibacterial drug classes. While most modifications of the original thiophene group compromised antibacterial activity, one selenophene analogue displayed (i) improved activity against the primary target enzyme DNA gyrase, (ii) similar activities against a panel of MRSA clinical isolates, and (iii) reduced hERG channel inhibition.