5‐((3r,5r,7r)‐adamantan‐1‐yl)piperazin‐2‐one | 924912-05-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5‐((3r,5r,7r)‐adamantan‐1‐yl)piperazin‐2‐one
• 英文别名: 5-(1-Adamantyl)piperazin-2-one
• CAS: 924912-05-0
• 化学式: C₁₄H₂₂N₂O
• 分子量: 234.341
• InChiKey: UYCJTZPUBLBMTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5‐((3r,5r,7r)‐adamantan‐1‐yl)piperazin‐2‐one 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 29.5h， 生成 3-Adamantan-1-yl-4-methyl-piperazine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Influence of an additional 2-amino substituent of the 1-aminoethyl pharmacophore group on the potency of rimantadine against influenza virus A

  摘要：

  We examined whether the incorporation of a second amino group into the 1-aminoethyl pharmacophore of rimantadine 2 and into the piperidine pharmacophore of the heterocyclic rimantadine 4 was compatible with anti-influenza virus A activity. The new synthetic molecules are capable of forming two hydrogen bonds within the receptor. We identified molecules 8 and 16, bearing the adamantyl and 1,2-diaminoethyl groups, which are equipotent to rimantadine 2 bearing the adamantyl and I-aminoethyl pharmacophore groups. Interestingly, diamino compound 16 is a 4-fold more potent inhibitor than its parent monoamino, heterocyclic rimantadine 4 propably because of additional hydrogen bonding interactions with the M2 protein receptor. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.092
• 作为产物：
  描述：

  1-金刚烷甲醛 在 platinum(IV) oxide 盐酸 、 氢气 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 54.0h， 生成 5‐((3r,5r,7r)‐adamantan‐1‐yl)piperazin‐2‐one
  参考文献：
  名称：

  Influence of an additional 2-amino substituent of the 1-aminoethyl pharmacophore group on the potency of rimantadine against influenza virus A

  摘要：

  We examined whether the incorporation of a second amino group into the 1-aminoethyl pharmacophore of rimantadine 2 and into the piperidine pharmacophore of the heterocyclic rimantadine 4 was compatible with anti-influenza virus A activity. The new synthetic molecules are capable of forming two hydrogen bonds within the receptor. We identified molecules 8 and 16, bearing the adamantyl and 1,2-diaminoethyl groups, which are equipotent to rimantadine 2 bearing the adamantyl and I-aminoethyl pharmacophore groups. Interestingly, diamino compound 16 is a 4-fold more potent inhibitor than its parent monoamino, heterocyclic rimantadine 4 propably because of additional hydrogen bonding interactions with the M2 protein receptor. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.092

文献信息

• Influence of an additional 2-amino substituent of the 1-aminoethyl pharmacophore group on the potency of rimantadine against influenza virus A
  作者：Dimitrios Tataridis、George Fytas、Antonios Kolocouris、Christos Fytas、Nicolas Kolocouris、George B. Foscolos、Elizaveta Padalko、Johan Neyts、Erik De Clercq

  DOI：10.1016/j.bmcl.2006.10.092

  日期：2007.2

  We examined whether the incorporation of a second amino group into the 1-aminoethyl pharmacophore of rimantadine 2 and into the piperidine pharmacophore of the heterocyclic rimantadine 4 was compatible with anti-influenza virus A activity. The new synthetic molecules are capable of forming two hydrogen bonds within the receptor. We identified molecules 8 and 16, bearing the adamantyl and 1,2-diaminoethyl groups, which are equipotent to rimantadine 2 bearing the adamantyl and I-aminoethyl pharmacophore groups. Interestingly, diamino compound 16 is a 4-fold more potent inhibitor than its parent monoamino, heterocyclic rimantadine 4 propably because of additional hydrogen bonding interactions with the M2 protein receptor. (c) 2006 Elsevier Ltd. All rights reserved.