4-Adamantan-1-yl-4-nitro-pentanoic acid ethyl ester | 888030-21-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-Adamantan-1-yl-4-nitro-pentanoic acid ethyl ester
• CAS: 888030-21-5
• 化学式: C₁₇H₂₇NO₄
• 分子量: 309.406
• InChiKey: JLOYERANJOJQCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-Adamantan-1-yl-4-nitro-pentanoic acid ethyl ester 在 盐酸 、 sodium hydroxide 作用下， 以 various solvents 为溶剂， 反应 6.0h， 生成 4-(tricyclo[3.3.1.13,7]dec-1-yl)-4-nitropentanoic acid methyl ester
  参考文献：
  名称：

  Heterocyclic rimantadine analogues with antiviral activity

  摘要：

  2-(1-Adamantyl)-2-methyl-pyrrolidines 3 and 4, 2-(1-adamatityl)-2-methyl-azetidines 5 and 6, and 2-(1-adamantyl)-2-methyl-aziridines 7 and 8 were synthesized and tested for their antiviral activity against influenza A. Parent molecules 3, 5, and 7 contain the alpha-methyl-1-adimantan-methanamine 2 pharmacophoric moiety (rimantadine). The ring size effect on anti-influenza A activity was investigated. Pyrrolidine 3 was the most potent anti-influenza virus A compound, 9-fold more potent than rimantadine 2, 27-fold more potent than amantadine 1, and 22-fold more potent than ribavirin. Azetidines 5 and 6 were both markedly active against influenza A H2N2 virus, 10- to 20-fold more potent than amantadine. Aziridine 7 was almost devoid of any activity against H2N2 virus but exhibited borderline activity against H3N2 influenza A strain. Thus, it appears that changing the five-, to four- to a three-membered ring results in a drop of activity against influenza A virus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.056
• 作为产物：
  描述：

  1-金刚烷乙胺 在 苄基三甲基氢氧化铵 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 1,2-二氯乙烷 、 叔丁醇 为溶剂， 反应 6.0h， 生成 4-Adamantan-1-yl-4-nitro-pentanoic acid ethyl ester
  参考文献：
  名称：

  Heterocyclic rimantadine analogues with antiviral activity

  摘要：

  2-(1-Adamantyl)-2-methyl-pyrrolidines 3 and 4, 2-(1-adamatityl)-2-methyl-azetidines 5 and 6, and 2-(1-adamantyl)-2-methyl-aziridines 7 and 8 were synthesized and tested for their antiviral activity against influenza A. Parent molecules 3, 5, and 7 contain the alpha-methyl-1-adimantan-methanamine 2 pharmacophoric moiety (rimantadine). The ring size effect on anti-influenza A activity was investigated. Pyrrolidine 3 was the most potent anti-influenza virus A compound, 9-fold more potent than rimantadine 2, 27-fold more potent than amantadine 1, and 22-fold more potent than ribavirin. Azetidines 5 and 6 were both markedly active against influenza A H2N2 virus, 10- to 20-fold more potent than amantadine. Aziridine 7 was almost devoid of any activity against H2N2 virus but exhibited borderline activity against H3N2 influenza A strain. Thus, it appears that changing the five-, to four- to a three-membered ring results in a drop of activity against influenza A virus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.056