4-(3-乙基氨基-吡啶-2-基)-哌嗪-1-羧酸叔丁酯 | 111669-26-2

• 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: 4-(3-乙基氨基-吡啶-2-基)-哌嗪-1-羧酸叔丁酯
• 英文名称: 4-(3-ethylaminopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 4-[3-(ethylamino)pyridin-2-yl]piperazine-1-carboxylate
• CAS: 111669-26-2
• 化学式: C₁₆H₂₆N₄O₂
• 分子量: 306.408
• InChiKey: MLMFCRUWVHXHIL-UHFFFAOYSA-N

物化性质

• 沸点：
  454.6±45.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3-乙基氨基-吡啶-2-基)-哌嗪-1-羧酸叔丁酯 在 盐酸 、 potassium carbonate 、 sodium iodide 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 58.0h， 生成 21-[4-(3-ethylamino-2-pyridinyl)-1-piperazinyl]-16α-methylpregna-1,4,9-(11)-triene-3,20-dione
  参考文献：
  名称：

  Novel 21-aminosteroids that inhibit iron-dependent lipid peroxidation and protect against central nervous system trauma

  摘要：

  A novel class of 21-aminosteroids has been developed. Compounds within this series are potent inhibitors of iron-dependent lipid peroxidation in rat brain homogenates with IC50's as low as 3 microM. Furthermore, selected members enhance early neurological recovery and survival in a mouse head injury model. Significant improvement in the 1 h post-head-injury neurological status (grip test score) by as much as 168.6% of the control has been observed. The most efficacious compound in this assay (30) showed an increase in the 1-week survival of 78.6% as compared to 27.3% for the vehicle-treated mice in the head-injury model. Based on its biological profile, 21-[4-(2,6-di-1-pyrrolidinyl-4-pyrimidinyl)-1-piperazinyl]-16 alpha- methylpregna-1,4,9(11)-triene-3,20-dione monomethanesulfonate (30) was selected for further evaluation and is currently entering phase I clinical trials for the treatment of head and spinal trauma.

  DOI：

  10.1021/jm00166a010
• 作为产物：
  描述：

  1-(3-硝基吡啶-2-基)哌嗪 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 25.0 ℃ 、317.16 kPa 条件下， 反应 80.0h， 生成 4-(3-乙基氨基-吡啶-2-基)-哌嗪-1-羧酸叔丁酯
  参考文献：
  名称：

  Novel 21-aminosteroids that inhibit iron-dependent lipid peroxidation and protect against central nervous system trauma

  摘要：

  A novel class of 21-aminosteroids has been developed. Compounds within this series are potent inhibitors of iron-dependent lipid peroxidation in rat brain homogenates with IC50's as low as 3 microM. Furthermore, selected members enhance early neurological recovery and survival in a mouse head injury model. Significant improvement in the 1 h post-head-injury neurological status (grip test score) by as much as 168.6% of the control has been observed. The most efficacious compound in this assay (30) showed an increase in the 1-week survival of 78.6% as compared to 27.3% for the vehicle-treated mice in the head-injury model. Based on its biological profile, 21-[4-(2,6-di-1-pyrrolidinyl-4-pyrimidinyl)-1-piperazinyl]-16 alpha- methylpregna-1,4,9(11)-triene-3,20-dione monomethanesulfonate (30) was selected for further evaluation and is currently entering phase I clinical trials for the treatment of head and spinal trauma.

  DOI：

  10.1021/jm00166a010

文献信息

• Piperazine and Piperidine MGLUR5 Potentiators
  申请人：Arora Jalaj

  公开号：US20100144710A1

  公开（公告）日：2010-06-10

  Compounds of Formula I or pharmaceutically acceptable salts or solvates thereof, wherein A, B, D, Ar1, Ar2, R2, R3, R4, a, m and n are defined in the specification, methods for the use thereof, processes for making and pharmaceutical compositions containing the same.

  公式I的化合物或其药学上可接受的盐或溶剂化物，其中A、B、D、Ar1、Ar2、R2、R3、R4、a、m和n在说明书中有定义，其使用方法、制备方法和含有它们的药物组合物。
• WO2008/112440
  申请人：——

  公开号：——

  公开（公告）日：——
• PIPERAZINE AND PIPERIDINE MGLUR5 POTENTIATORS
  申请人：AstraZeneca AB

  公开号：EP2134687A1

  公开（公告）日：2009-12-23
• [EN] PIPERAZINE AND PIPERIDINE MGLUR5 POTENTIATORS<br/>[FR] PIPÉRAZINE ET POTENTIALISATEURS MGLUR5 DE PIPÉRIDINE
  申请人：ASTRAZENECA AB

  公开号：WO2008112440A1

  公开（公告）日：2008-09-18

  [EN] Compounds of Formula I or pharmaceutically acceptable salts or solvates thereof, wherein A, B, D, Ar1, Ar2, R2, R3, R4, a, m and n are defined in the specification, methods for the use thereof, processes for making and pharmaceutical compositions containing the same.
  [FR] L'invention concerne des composés de formule I ou leurs sels ou leurs solvates pharmaceutiquement acceptables, où A, B, D, Ar1, Ar2, R2, R3, R4, a, m et n sont définis dans le mémoire, des procédés d'utilisation de ceux-ci, des procédés de fabrication et des compositions pharmaceutiques les contenant.
• Novel 21-aminosteroids that inhibit iron-dependent lipid peroxidation and protect against central nervous system trauma
  作者：E. Jon Jacobsen、John M. McCall、Donald E. Ayer、Fred J. VanDoornik、John R. Palmer、Kenneth L. Belonga、J. Mark Braughler、Edward D. Hall、David J. Houser

  DOI：10.1021/jm00166a010

  日期：1990.4

  A novel class of 21-aminosteroids has been developed. Compounds within this series are potent inhibitors of iron-dependent lipid peroxidation in rat brain homogenates with IC50's as low as 3 microM. Furthermore, selected members enhance early neurological recovery and survival in a mouse head injury model. Significant improvement in the 1 h post-head-injury neurological status (grip test score) by as much as 168.6% of the control has been observed. The most efficacious compound in this assay (30) showed an increase in the 1-week survival of 78.6% as compared to 27.3% for the vehicle-treated mice in the head-injury model. Based on its biological profile, 21-[4-(2,6-di-1-pyrrolidinyl-4-pyrimidinyl)-1-piperazinyl]-16 alpha- methylpregna-1,4,9(11)-triene-3,20-dione monomethanesulfonate (30) was selected for further evaluation and is currently entering phase I clinical trials for the treatment of head and spinal trauma.