2-(1-adamantyl)-2-methyl-pyrrolidine | 888030-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-(1-adamantyl)-2-methyl-pyrrolidine
• 英文别名: 2-(1-Adamantyl)-2-methylpyrrolidine
• CAS: 888030-31-7
• 化学式: C₁₅H₂₅N
• 分子量: 219.37
• InChiKey: JQQSEBALQVRCLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1-adamantyl)-2-methyl-pyrrolidine 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 48.0h， 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 盐酸 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 氢气 、 镍 作用下， 以 四氢呋喃 、 乙醇 、 various solvents 为溶剂， 50.0~80.0 ℃ 、344.74 kPa 条件下， 反应 35.0h， 生成 2-(1-adamantyl)-2-methyl-pyrrolidine
  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

文献信息

• Compositions and kits for treating influenza
  申请人：Adamas Pharmaceuticals, Inc.

  公开号：EP2450040A2

  公开（公告）日：2012-05-09

  Compositions, kits and methods are provided for the treatment or prophylaxis of influenza

  提供了用于治疗或预防流感的组合物、试剂盒和方法
• Synthetic catalase/superoxide dismutase mimetics and methods for treating viral infections
  申请人：THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH & HUMAN SERVICES

  公开号：US10683316B2

  公开（公告）日：2020-06-16

  The invention provides for the treatment of disorders related to viral infection, using salen manganese compounds.

  本发明利用沙林锰化合物治疗与病毒感染有关的疾病。
• COMPOSITIONS AND KITS FOR TREATING INFLUENZA
  申请人：Adamas Pharmaceuticals, Inc.

  公开号：EP2142192B1

  公开（公告）日：2012-02-15
• METHODS FOR SCREENING SUBSTANCES CAPABLE OF MODULATING THE REPLICATION OF AN INFLUENZA VIRUS
  申请人：Institut National de la Santé et de la Recherche Médicale (INSERM)

  公开号：EP2710381A2

  公开（公告）日：2014-03-26
• ANTIVIRAL THERAPIES WITH PHOSPHOLIPASE D INHIBITORS
  申请人：Vanderbilt University

  公开号：EP2760447A1

  公开（公告）日：2014-08-06