6-(3-吡啶基氧基)-1-己醇 | 91067-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-(3-吡啶基氧基)-1-己醇
• 中文别名: 1-己醇,6-(3-吡啶氧基)-
• 英文名称: 6-(pyridin-3-yloxy)-hexan-1-ol
• 英文别名: 6-Pyridin-3-yloxyhexan-1-ol
• CAS: 91067-10-6
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: NISMFYWISMHLDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(3-吡啶基氧基)-1-己醇 在 silica gel 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 6-(pyridin-3-yloxy)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
• 作为产物：
  描述：

  3-羟基吡啶 、 6-氯-1-己醇 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以66%的产率得到6-(3-吡啶基氧基)-1-己醇
  参考文献：
  名称：

  化学酶法合成和对2-和3-羟基吡啶衍生物的生物学评价墨西哥利什曼原虫

  摘要：

  合成了一系列的2-和3-羟基吡啶的羟烷基和酰氧基烷基衍生物，并评价了它们作为原生动物利什曼原虫的生长抑制剂的生物学活性。通过化学酶学方法在两个反应步骤中获得了三十种新化合物。研究了酶促反应中各种反应参数的影响，如酶的来源，酰化剂/底物的比例，酶/底物的比例，溶剂和温度等。一些被评估的化合物显示出显着的活性，如墨西哥利什曼原虫生长抑制剂，使用乙酰化衍生物可获得最佳效果。酶法所显示的优点，例如温和的反应条件和对环境的低影响，使生物催化成为制备取代吡啶的这些衍生物的便捷方法，并可用作潜在的抗寄生虫剂。

  DOI：

  10.1016/j.bmc.2012.06.028

文献信息

• Design, Synthesis, and Biological Evaluation of <i>N</i>-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection
  作者：Wenquan Yu、Tina Gill、Lijuan Wang、Yanming Du、Hong Ye、Xiaowang Qu、Ju-Tao Guo、Andrea Cuconati、Kang Zhao、Timothy M. Block、Xiaodong Xu、Jinhong Chang

  DOI：10.1021/jm300171v

  日期：2012.7.12

  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%).
• Chemoenzymatic synthesis and biological evaluation of 2- and 3-hydroxypyridine derivatives against Leishmania mexicana
  作者：Guadalupe García Liñares、Gonzalo Parraud、Carlos Labriola、Alicia Baldessari

  DOI：10.1016/j.bmc.2012.06.028

  日期：2012.8

  temperature, was studied. Some of the evaluated compounds showed a remarkable activity as Leishmania mexicana growth inhibitors, obtaining the best results with the acetylated derivatives. The advantages showed by the enzymatic methodology, such as mild reaction conditions and low environmental impact, make the biocatalysis a convenient way to prepare these derivatives of substituted pyridines with application

  合成了一系列的2-和3-羟基吡啶的羟烷基和酰氧基烷基衍生物，并评价了它们作为原生动物利什曼原虫的生长抑制剂的生物学活性。通过化学酶学方法在两个反应步骤中获得了三十种新化合物。研究了酶促反应中各种反应参数的影响，如酶的来源，酰化剂/底物的比例，酶/底物的比例，溶剂和温度等。一些被评估的化合物显示出显着的活性，如墨西哥利什曼原虫生长抑制剂，使用乙酰化衍生物可获得最佳效果。酶法所显示的优点，例如温和的反应条件和对环境的低影响，使生物催化成为制备取代吡啶的这些衍生物的便捷方法，并可用作潜在的抗寄生虫剂。