4-(tricyclo[3.3.1.13,7]dec-1-yl)-4-nitropentanoic acid | 888030-22-6

• 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-(tricyclo[3.3.1.13,7]dec-1-yl)-4-nitropentanoic acid
• 英文别名: 4-(tricyclo[3.3.1.1^3,7]dec-1-yl)-4-nitropentanoic acid
• CAS: 888030-22-6
• 化学式: C₁₅H₂₃NO₄
• 分子量: 281.352
• InChiKey: LFUUMIQLCIPKMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  80.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(tricyclo[3.3.1.13,7]dec-1-yl)-4-nitropentanoic acid 在 盐酸 、 lithium aluminium tetrahydride 、 氢气 、 镍 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 25.0~75.0 ℃ 、344.74 kPa 条件下， 反应 80.0h， 生成 2-(tricyclo[3.3.1.1^3,7]dec-1-yl)-N,2-dimethylpyrrolidine hydrochloride
  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：

  4-Adamantan-1-yl-4-nitro-pentanoic acid ethyl ester 在 sodium hydroxide 作用下， 以 various solvents 为溶剂， 反应 3.0h， 以14.51 g的产率得到4-(tricyclo[3.3.1.13,7]dec-1-yl)-4-nitropentanoic acid
  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