6-(2-Methoxyphenoxy)hexan-1-ol | 1383151-31-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-(2-Methoxyphenoxy)hexan-1-ol
• CAS: 1383151-31-2
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: KHNAQNYSXNBFKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  341.0±22.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(2-Methoxyphenoxy)hexan-1-ol 在 silica gel 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成 (2R,3R,4R,5S)-2-(hydroxymethyl)-1-(6-(2-methoxyphenoxy)hexyl)piperidine-3,4,5-triol
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of N-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection

  摘要：

  We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENY) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENY in BHK cells of 6.5 mu M, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 mu M) against DENY infection, while maintaining low cytotoxicity (CC50 > 500 mu M, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 +/- 4%).

  DOI：

  10.1021/jm300171v
• 作为产物：
  描述：

  6-溴正己醇 、 木榴油 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 6-(2-Methoxyphenoxy)hexan-1-ol
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of N-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection

  摘要：

  We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENY) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENY in BHK cells of 6.5 mu M, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 mu M) against DENY infection, while maintaining low cytotoxicity (CC50 > 500 mu M, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 +/- 4%).

  DOI：

  10.1021/jm300171v

文献信息

• Vernetzbare, photoaktive Silanderivate
  申请人：Rolic AG

  公开号：EP0844248A2

  公开（公告）日：1998-05-27

  Die Erfindung betrifft neue vernetzbare, photoaktive Silan Derivate und Mischungen mit 3-Aryl-acrylsäureestern und -amiden, sowie deren Verwendung als Orientierungsschichten für Flüssigkristalle und zum Aufbau unstrukturierter bzw. strukturierter optischer Elemente und Mehrschichtsysteme.

  本发明涉及新的可交联光活性硅烷衍生物和与 3-芳基丙烯酸酯和酰胺的混合物，以及它们作为液晶定向层和用于构建非结构化或结构化光学元件和多层系统的用途。