1-(2-aminoethyl)tricyclo[3.3.1.1(3,7)]decan-2-ol | 1257334-41-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-aminoethyl)tricyclo[3.3.1.1(3,7)]decan-2-ol
• 英文别名: 1-(2-Aminoethyl)adamantan-2-ol
• CAS: 1257334-41-0
• 化学式: C₁₂H₂₁NO
• 分子量: 195.305
• InChiKey: DGCFRHFPJKCHTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(2-aminoethyl)tricyclo[4.3.1.0(3,8)]decan-4-ol 在 硫酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以96%的产率得到1-(2-aminoethyl)tricyclo[3.3.1.1(3,7)]decan-2-ol
  参考文献：
  名称：

  Design and synthesis of bioactive adamantanaminoalcohols and adamantanamines

  摘要：

  Adamantanamines 16, 18, 21, 24, 27, 28, 30, 32, 35, 36, 37, 40, 46 and 48 were synthesized and tested for anti-influenza A virus and trypanocidal activity. The stereoelectronic requirements for optimal antiviral and trypanocidal potency were investigated. The effect of introducing a hydroxyl group close to the amino group on this class of compounds was examined for the first time. Aminoalcohol 24 proved to be the most active of the compounds tested against influenza A virus, being 6-fold more active than amantadine, equipotent to rimantadine and 26-fold more potent than ribavirin. Aminoalcohols 36 and 37 were found to have considerable activity against bloodstream forms of the African trypanosome, Trypanosoma brucei, being almost 10 times more potent than rimantadine. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.009

文献信息

• Design and synthesis of bioactive adamantanaminoalcohols and adamantanamines
  作者：Grigoris Zoidis、Nicolas Kolocouris、John M. Kelly、S. Radhika Prathalingam、Lieve Naesens、Erik De Clercq

  DOI：10.1016/j.ejmech.2010.08.009

  日期：2010.11

  Adamantanamines 16, 18, 21, 24, 27, 28, 30, 32, 35, 36, 37, 40, 46 and 48 were synthesized and tested for anti-influenza A virus and trypanocidal activity. The stereoelectronic requirements for optimal antiviral and trypanocidal potency were investigated. The effect of introducing a hydroxyl group close to the amino group on this class of compounds was examined for the first time. Aminoalcohol 24 proved to be the most active of the compounds tested against influenza A virus, being 6-fold more active than amantadine, equipotent to rimantadine and 26-fold more potent than ribavirin. Aminoalcohols 36 and 37 were found to have considerable activity against bloodstream forms of the African trypanosome, Trypanosoma brucei, being almost 10 times more potent than rimantadine. (C) 2010 Elsevier Masson SAS. All rights reserved.