2-Adamantan-1-yl-1-methyl-piperazine | 924912-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-Adamantan-1-yl-1-methyl-piperazine
• 英文别名: 1-Adamantyl-methyl-piperazine；2-(1-adamantyl)-1-methylpiperazine
• CAS: 924912-08-3
• 化学式: C₁₅H₂₆N₂
• 分子量: 234.385
• InChiKey: LIXAHVSDLVQZOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 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：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Adamantan-1-yl-1-methyl-piperazine 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 2-Adamantan-1-yl-1,4-dimethyl-piperazine
  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：

  5-Adamantan-1-yl-4-methyl-piperazin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以90%的产率得到2-Adamantan-1-yl-1-methyl-piperazine
  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

• 11-(Piperazino-acetyl)-5,11-di
  申请人：Boehringer Ingelheim GmbH

  公开号：US04213984A1

  公开（公告）日：1980-07-22

  Compounds of the formula ##STR1## wherein R.sub.1 is alkyl of 3 to 12 carbon atoms; unsaturated aliphatic hydrocarbyl of 3 to 20 carbon atoms comprising 1 to 3 double bonds and/or one triple bond; phenyl(alkyl of 2 to 4 carbon atoms); methylenedioxybenzyl; chlorobenzyl; indan-5-ylmethyl; indan-3-ylmethyl; phenyl(alkenyl of 2 to 4 carbon atoms); cycloalkyl of 5 to 7 carbon atoms; (cycloalkyl of 3 to 10 carbon atoms)methyl; (methylcycloalkyl of 4 to 11 carbon atoms)methyl; morpholino(alkyl of 2 to 3 carbon atoms); pyrrolidino(alkyl of 2 to 3 carbon atoms); piperidino (alkyl of 2 to 3 carbon atoms); 4-methylpiperazino(alkyl of 2 to 3 carbon atoms); or, when R.sub.3 and/or R.sub.4 are methyl or ethyl, also methyl or ethyl; R.sub.2 is hydrogen, methyl or ethyl; and R.sub.3 and R.sub.4 are each hydrogen, methyl or ethyl; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as the salts are useful as anti-ulcerogenics and secretion inhibitors.

  化合物的化学式为##STR1## 其中R.sub.1为3至12个碳原子的烷基；3至20个碳原子的不饱和脂肪族烃基，包括1至3个双键和/或一个三键；苯基（2至4个碳原子的烷基）；亚甲二氧基苯基甲基；氯苯基甲基；茚-5-基甲基；茚-3-基甲基；苯基（2至4个碳原子的烯基）；5至7个碳原子的环烷基；（3至10个碳原子的环烷基）甲基；（4至11个碳原子的甲基环烷基）甲基；吗啉基（2至3个碳原子的烷基）；吡咯烷基（2至3个碳原子的烷基）；哌啶基（2至3个碳原子的烷基）；4-甲基哌嗪基（2至3个碳原子的烷基）；当R.sub.3和/或R.sub.4为甲基或乙基时，也可以是甲基或乙基；R.sub.2为氢、甲基或乙基；R.sub.3和R.sub.4均为氢、甲基或乙基；以及其非毒性、药理学上可接受的酸盐。这些化合物及其盐可用作抗溃疡剂和分泌抑制剂。
• 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.