2-甲基-1-(1-氧代丙基)-哌嗪 | 314729-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 2-甲基-1-(1-氧代丙基)-哌嗪
• 中文别名: 3-甲基苯基2-(氨基甲氧基)-4-氯苯酸酯
• 英文名称: 2-methyl-1-propionylpiperazine
• 英文别名: 1-(2-Methylpiperazin-1-yl)propan-1-one
• CAS: 314729-13-0
• 化学式: C₈H₁₆N₂O
• 分子量: 156.228
• InChiKey: NVHDXJUEWXIXSH-UHFFFAOYSA-N

物化性质

• 沸点：
  277.1±33.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 2-甲基-1-(1-氧代丙基)-哌嗪 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以70%的产率得到DM312
  参考文献：
  名称：

  Molecular Simplification of 1,4-Diazabicyclo[4.3.0]nonan-9-ones Gives Piperazine Derivatives That Maintain High Nootropic Activity

  摘要：

  Several 4-substituted 1-acylpiperazines, obtained by molecular simplification of 4-substituted 1,4-diazabicyclo[4.3.0]nonan-9-ones, have been synthesized and tested in vivo on the mouse passive avoidance test, to evaluate their nootropic activity. The results show that, apparently, an N-acylpiperazine group can mimic the 2-pyrrolidinone ring of 1,4-diazabicyclo[4.3.0]nonan-9-one, as the compounds of the new series maintain high nootropic activity. Moreover molecular simplification produces more clear-cut structure-activity relationships with respect to the parent series. The mechanism of action also appears to be similar in the two series. In fact, although the molecular mechanism remains to be elucidated, the most potent compound of each class (DM232 and 13, DM235) is able to increase acetylcholine release in rat brain. Piperazine derivatives represent a new class of nootropic drugs with an in vivo pharmacological profile very similar to that of piracetam, showing much higher potency with respect to the reference compound. Among the compounds studied, 13 (DM235) shows outstanding potency, being active at a dose of 0.001 mg kg(-1) sc.

  DOI：

  10.1021/jm000972h
• 作为产物：
  描述：

  2-甲基哌嗪 在 10percent Pd/C 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 50.0 ℃ 、324.06 kPa 条件下， 反应 12.0h， 生成 2-甲基-1-(1-氧代丙基)-哌嗪
  参考文献：
  名称：

  Molecular Simplification of 1,4-Diazabicyclo[4.3.0]nonan-9-ones Gives Piperazine Derivatives That Maintain High Nootropic Activity

  摘要：

  Several 4-substituted 1-acylpiperazines, obtained by molecular simplification of 4-substituted 1,4-diazabicyclo[4.3.0]nonan-9-ones, have been synthesized and tested in vivo on the mouse passive avoidance test, to evaluate their nootropic activity. The results show that, apparently, an N-acylpiperazine group can mimic the 2-pyrrolidinone ring of 1,4-diazabicyclo[4.3.0]nonan-9-one, as the compounds of the new series maintain high nootropic activity. Moreover molecular simplification produces more clear-cut structure-activity relationships with respect to the parent series. The mechanism of action also appears to be similar in the two series. In fact, although the molecular mechanism remains to be elucidated, the most potent compound of each class (DM232 and 13, DM235) is able to increase acetylcholine release in rat brain. Piperazine derivatives represent a new class of nootropic drugs with an in vivo pharmacological profile very similar to that of piracetam, showing much higher potency with respect to the reference compound. Among the compounds studied, 13 (DM235) shows outstanding potency, being active at a dose of 0.001 mg kg(-1) sc.

  DOI：

  10.1021/jm000972h

文献信息

• AMIDES AS INHIBITORS FOR PYRUVATE DEHYDROGENASE
  申请人：AstraZeneca AB

  公开号：EP1214287A1

  公开（公告）日：2002-06-19
• [EN] AMIDES AS INHIBITORS FOR PYRUVATE DEHYDROGENASE<br/>[FR] AMIDES INHIBITEURS POUR LA PYRUVATE DESHYDROGENASE
  申请人：ASTRAZENECA AB

  公开号：WO2001017942A1

  公开（公告）日：2001-03-15

  A compound of formula (I) wherein: Ring A is a nitrogen linked mono or bicyclic heterocyclic ring as defined within; R?1 and R2¿ are independently C¿1-3?alkyl optionally substituted by fluoro or chloro; or R?1 and R2¿ together with the carbon atom to which they are attached, form a C¿3-5?cylcoalkyl ring optionally substituted by fluoro; R?3¿ is as defined within; and n is 0-5; wherein the values of R3 may be the same or different; or a pharmaceutically acceptable salt or an in vivo hydrolysable ester thereof is described. The use of compounds of formula (I) in the production of an elevation of PDH activity in a warm-blooded animal such as a human being are also described. Pharmaceutical compositions, methods and processes for preparation of compounds of formula (I) are detailed.
• Molecular Simplification of 1,4-Diazabicyclo[4.3.0]nonan-9-ones Gives Piperazine Derivatives That Maintain High Nootropic Activity
  作者：Dina Manetti、Carla Ghelardini、Alessandro Bartolini、Silvia Dei、Nicoletta Galeotti、Fulvio Gualtieri、Maria Novella Romanelli、Elisabetta Teodori

  DOI：10.1021/jm000972h

  日期：2000.11.1

  Several 4-substituted 1-acylpiperazines, obtained by molecular simplification of 4-substituted 1,4-diazabicyclo[4.3.0]nonan-9-ones, have been synthesized and tested in vivo on the mouse passive avoidance test, to evaluate their nootropic activity. The results show that, apparently, an N-acylpiperazine group can mimic the 2-pyrrolidinone ring of 1,4-diazabicyclo[4.3.0]nonan-9-one, as the compounds of the new series maintain high nootropic activity. Moreover molecular simplification produces more clear-cut structure-activity relationships with respect to the parent series. The mechanism of action also appears to be similar in the two series. In fact, although the molecular mechanism remains to be elucidated, the most potent compound of each class (DM232 and 13, DM235) is able to increase acetylcholine release in rat brain. Piperazine derivatives represent a new class of nootropic drugs with an in vivo pharmacological profile very similar to that of piracetam, showing much higher potency with respect to the reference compound. Among the compounds studied, 13 (DM235) shows outstanding potency, being active at a dose of 0.001 mg kg(-1) sc.