| 913336-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• CAS: 913336-02-4
• 化学式: C₁₈H₂₈BrNO
• 分子量: 354.33
• InChiKey: IEDCLZDZQSTRQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Synthesis, conformational characteristics and anti-influenza virus A activity of some 2-adamantylsubstituted azacycles

  摘要：

  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.

  DOI：

  10.1016/j.bioorg.2006.05.004
• 作为产物：
  描述：

  在 platinum(IV) oxide 氢气 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  Synthesis, conformational characteristics and anti-influenza virus A activity of some 2-adamantylsubstituted azacycles

  摘要：

  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.

  DOI：

  10.1016/j.bioorg.2006.05.004