4-(alpha,beta)-羟基金刚乙胺 | 117821-36-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-(alpha,beta)-羟基金刚乙胺
• 英文名称: 1-(1-aminoethyl)-4-adamantanol
• 英文别名: p-Hydroxyrimantadine；5-(1-aminoethyl)adamantan-2-ol
• CAS: 117821-36-0；133908-83-5
• 化学式: C₁₂H₂₁NO
• 分子量: 195.305
• InChiKey: IKZHOAXNYUBUDD-UHFFFAOYSA-N

物化性质

• 沸点：
  305.7±15.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-金刚烷酮-5-甲酸 在 吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 盐酸羟胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 22.0h， 生成 4-(alpha,beta)-羟基金刚乙胺
  参考文献：
  名称：

  Synthesis and antiviral activity of metabolites of rimantadine

  摘要：

  The hydroxy metabolites of rimantadine (3-5) were synthesized and compared to amantadine (1) and rimantadine (2) for their ability to inhibit the replication of influenza viruses in vitro. All three metabolites were inhibitory to wild-type influenza A viruses (H3N2 and H1N1). In particular, 2-hydroxyrimantadine (3) showed similar activity to amantadine, but the 3- and 4-hydroxy metabolites (4 and 5, respectively), both of which are found in rimantadine-treated patients, showed only modest inhibitory activity. A rimantadine-resistant isolate of influenza A virus exhibited cross-resistance to amantadine and to each of the metabolites 3-5. None of the compounds were effective against influenza B virus.

  DOI：

  10.1021/jm00169a029

文献信息

• US8088918B2
  申请人：——

  公开号：US8088918B2

  公开（公告）日：2012-01-03
• Synthesis and antiviral activity of metabolites of rimantadine
  作者：Percy S. Manchand、Richard L. Cerruti、Joseph A. Martin、Christopher H. Hill、John H. Merrett、Elizabeth Keech、Robert B. Belshe、Edward V. Connell、Iain S. Sim

  DOI：10.1021/jm00169a029

  日期：1990.7

  The hydroxy metabolites of rimantadine (3-5) were synthesized and compared to amantadine (1) and rimantadine (2) for their ability to inhibit the replication of influenza viruses in vitro. All three metabolites were inhibitory to wild-type influenza A viruses (H3N2 and H1N1). In particular, 2-hydroxyrimantadine (3) showed similar activity to amantadine, but the 3- and 4-hydroxy metabolites (4 and 5, respectively), both of which are found in rimantadine-treated patients, showed only modest inhibitory activity. A rimantadine-resistant isolate of influenza A virus exhibited cross-resistance to amantadine and to each of the metabolites 3-5. None of the compounds were effective against influenza B virus.