ethyl 1'-methylspiro[adamantane-2,2'-piperazine]-4'-carboxylate | 1312935-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: ethyl 1'-methylspiro[adamantane-2,2'-piperazine]-4'-carboxylate
• CAS: 1312935-63-9
• 化学式: C₁₇H₂₈N₂O₂
• 分子量: 292.422
• InChiKey: TYTKVFRIRLKCDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  32.78
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 1'-methylspiro[adamantane-2,2'-piperazine]-4'-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到1,4-dimethylspiro[piperazine-2,2'-tricyclo[3.3.1.1(3,7)]decane]
  参考文献：
  名称：

  Influence of an additional amino group on the potency of aminoadamantanes against influenza virus A. II – Synthesis of spiropiperazines and in vitro activity against influenza A H3N2 virus

  摘要：

  Spiro[piperidine-2,2'-adamantane] 4 is one of the most potent synthetic anti-influenza A aminoadamantanes or other cage structure amines tested so far. Based on previous results Tataridis et al. (2007) [5h] which demonstrate the boost of in vitro potency by the presence of an additional amino group, we examined whether the incorporation of a second amino group into this heterocycle would increase the anti-influenza A virus activity. The new synthetic molecules 5-7 are capable of forming two hydrogen bonds within the receptor. We identified the diamino derivatives 5 and 6, which are active against influenza A H3N2 virus although less potent than amantadine and its equipotent spiropiperidine 4. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2010.09.001
• 作为产物：
  描述：

  1-methylspiro[piperazine-2,2'-tricyclo[3.3.1.1(3,7)]decane] 、 氯甲酸乙酯 在 三乙胺 作用下， 以 乙醚 为溶剂， 以62%的产率得到ethyl 1'-methylspiro[adamantane-2,2'-piperazine]-4'-carboxylate
  参考文献：
  名称：

  Influence of an additional amino group on the potency of aminoadamantanes against influenza virus A. II – Synthesis of spiropiperazines and in vitro activity against influenza A H3N2 virus

  摘要：

  Spiro[piperidine-2,2'-adamantane] 4 is one of the most potent synthetic anti-influenza A aminoadamantanes or other cage structure amines tested so far. Based on previous results Tataridis et al. (2007) [5h] which demonstrate the boost of in vitro potency by the presence of an additional amino group, we examined whether the incorporation of a second amino group into this heterocycle would increase the anti-influenza A virus activity. The new synthetic molecules 5-7 are capable of forming two hydrogen bonds within the receptor. We identified the diamino derivatives 5 and 6, which are active against influenza A H3N2 virus although less potent than amantadine and its equipotent spiropiperidine 4. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2010.09.001