6-((3,4-dimethylcyclohexyl)oxy)hexanal | 1383153-65-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-((3,4-dimethylcyclohexyl)oxy)hexanal
• CAS: 1383153-65-8
• 化学式: C₁₄H₂₆O₂
• 分子量: 226.359
• InChiKey: NUXYHRNMRZAFEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-脱氧野尻霉素 、 6-((3,4-dimethylcyclohexyl)oxy)hexanal 在 溶剂黄146 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 25.0h， 以87%的产率得到(2R,3R,4R,5S)-1-(6-((3,4-dimethylcyclohexyl)oxy)hexyl)-2-(hydroxymethyl)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-(苄氧基)-1-己醇 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 silica gel 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.5h， 生成 6-((3,4-dimethylcyclohexyl)oxy)hexanal
  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