2-(2-piperidinyl)tricyclo[3.3.1.1^3,7]decan-2-ol | 259228-61-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(2-piperidinyl)tricyclo[3.3.1.1^3,7]decan-2-ol
• 英文别名: 2-(2-piperidinyl)-2-adamantanol；2-Piperidin-2-yladamantan-2-ol
• CAS: 259228-61-0
• 化学式: C₁₅H₂₅NO
• 分子量: 235.37
• InChiKey: BZHUMCQXPNKZAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-piperidinyl)tricyclo[3.3.1.1^3,7]decan-2-ol 在 氢氧化钾 、 sodium tetrahydroborate 、 氯化亚砜 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 62.0h， 生成 2-Adamantan-2-yl-piperidine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  2-（2-金刚烷基）哌啶的合成和结构抗流感病毒使用NMR光谱学和分子建模相结合的活性关系研究。

  摘要：

  合成2-（2-金刚烷基）哌啶13和15a-c，并评估其抗流感病毒A和B的活性。母体NH化合物13对H2N2流感A的活性比金刚烷胺和金刚烷胺高3-4倍。13的N-烷基化导致衍生物15a-c缺乏生物活性。从计算化学和NMR光谱学的结合推论，这种生物活性的显着降低可能归因于NH和N-烷基哌啶之间的构象性质不同。

  DOI：

  10.1016/s0960-894x(99)00631-9
• 作为产物：
  描述：

  2-吡啶基锂 在 platinum(IV) oxide 氢气 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 生成 2-(2-piperidinyl)tricyclo[3.3.1.1^3,7]decan-2-ol
  参考文献：
  名称：

  2-（2-金刚烷基）哌啶的合成和结构抗流感病毒使用NMR光谱学和分子建模相结合的活性关系研究。

  摘要：

  合成2-（2-金刚烷基）哌啶13和15a-c，并评估其抗流感病毒A和B的活性。母体NH化合物13对H2N2流感A的活性比金刚烷胺和金刚烷胺高3-4倍。13的N-烷基化导致衍生物15a-c缺乏生物活性。从计算化学和NMR光谱学的结合推论，这种生物活性的显着降低可能归因于NH和N-烷基哌啶之间的构象性质不同。

  DOI：

  10.1016/s0960-894x(99)00631-9

文献信息

• Synthesis, conformational characteristics and anti-influenza virus A activity of some 2-adamantylsubstituted azacycles
  作者：Despina Setaki、Dimitris Tataridis、George Stamatiou、Antonios Kolocouris、George B. Foscolos、George Fytas、Nicolas Kolocouris、Elizaveta Padalko、Johan Neyts、Erik De Clercq

  DOI：10.1016/j.bioorg.2006.05.004

  日期：2006.10

  The broad-spectrum antiviral activity of 2-(2-adamantyl)piperidines 11, 13a,b, and 15, 3-(2-adamantyl)pyrrolidines 27, 21a-g and 2-(2-adamantylmethyl)piperidines 30, 32a-c, and 35a-d was examined. Several compounds in the new series were potent against influenza A H3N2 virus. When 1-aminoethyl pharmacophore group of 2-rimantadine 4 (2-isomer of rimantadine) is included into a saturated nitrogen heterocycle, see compound 11, potency was retained. The diamine derivatives 21e-g and particularly 35a-c possessing three pharmocophoric groups, that is, the adamantyl and the two amine groups, exhibited high potency. The new compounds did not afford specific activity at non-toxic concentrations against any of the other viruses tested. According to NMR spectroscopy and molecular mechanics calculations it is striking that the parent structures 11 and 27 adopt a fixed trans conformation around C2-C2' bond. In the parent amines, which proved to be active compounds, the distance between nitrogen and adamantyl pharmacophoric groups was different; N-C2' distance is 3.7, 3.8 angstrom for 27, 30 and 2.5 angstrom for 11 suggesting that M2 receptor site can accommodate different in size and orientation lipophilic cages. (c) 2006 Elsevier Inc. All rights reserved.
• 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.