4-(1-哌嗪)-2,6-双-(1-吡咯烷)-嘧啶 | 111641-17-9

• 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-(1-哌嗪)-2,6-双-(1-吡咯烷)-嘧啶
• 英文名称: 4-(1-piperazinyl)-2,6-di-1-pyrrolidinylpyrimidine
• 英文别名: 4-(piperazin-1-yl)-2,6-di(pyrrolidin-1-yl)pyrimidine；2,4-bis(1-pyrrolidinyl)-6-(1-piperazinyl)-pyrimidine；4-piperazin-1-yl-2,6-dipyrrolidin-1-ylpyrimidine
• CAS: 111641-17-9
• 化学式: C₁₆H₂₆N₆
• 分子量: 302.423
• InChiKey: XTPTVAPEXHUUDR-UHFFFAOYSA-N

物化性质

• 熔点：
  177-178 °C
• 沸点：
  553.2±60.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  47.5
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-(1-哌嗪)-2,6-双-(1-吡咯烷)-嘧啶 在 溴 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 4-<4-(tert-Butoxycarbonyl)-1-piperazinyl>-2,6-bis(1-pyrrolidinyl)-5-acetylpyrimidine
  参考文献：
  名称：

  Bromine-Mediated Addition of Nucleophiles to the Electron-Rich Pyrimidine Subunit of Tirilazad

  摘要：

  DOI：

  10.1021/jo00096a068
• 作为产物：
  描述：

  哌嗪 、 2,4-di(1-pyrrolidinyl)-6-chloropyrimidine 在 吡啶 作用下， 反应 50.0h， 以83%的产率得到4-(1-哌嗪)-2,6-双-(1-吡咯烷)-嘧啶
  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

• Amines useful in producing pharmaceutically active CNS compounds
  申请人：Upjohn Company

  公开号：US05099019A1

  公开（公告）日：1992-03-24

  Disclosed are .DELTA..sup.9(11) -steroids (VI) and amino substituted steroids (XI) which contain an amino group attached to the terminal carbon atom of the C.sub.17 -side chain, more particularly amino steroids (Ia and Ib), aromatic steroids (II), .DELTA..sup.16 -steroids (IIIa and IIIb), reduced A-ring steroids (IV), .DELTA..sup.17(20) -steroids (Va and Vb) and .DELTA..sup.9(11) -steroids (VI) which are useful as pharmaceutical agents for treating a number of conditions.

  披露了包含连接到C.sub.17-侧链的末端碳原子的氨基类固醇（VI）和氨基取代类固醇（XI），更具体地是氨基类固醇（Ia和Ib），芳香类固醇（II），Δ9(11)-类固醇（IIIa和IIIb），还原A环类固醇（IV），Δ17(20)-类固醇（Va和Vb）和Δ9(11)-类固醇（VI），这些类固醇可用作治疗多种疾病的药物。
• Cyclic Voltammetry as an Indicator of Antioxidant Activity
  作者：A. Papanikos、J. Eklund、W. R. Jackson、V. B. Kenche、E. M. Campi、A. D. Robertson、B. Jarrott、P. M. Beart、F. E. Munro、J. K. Callaway

  DOI：10.1071/ch01193

  日期：——

  A series of compounds based around combining the neuroprotective properties of non-competitive N-methyl D-aspartic acid (NMDA) receptor antagonists with antioxidant functionalities have been prepared. The redox chemistry of these compounds has been evaluated using cyclic voltammetry, and the results have been compared with their radical-scavenging properties obtained from two standard biological assays, the inhibition of lipid peroxidation (thiobarbituric acid reacting substances assay) and the Sapphire colorimetric assay. Results from these different methods show general concordance. The most effective antioxidants were substituted phenols, e.g. Trolox�. The antioxidant activity of a series of pyrimidines was shown to be dependent on the presence of three amino substituents.

  围绕非竞争性 N-甲基-D-天冬氨酸（NMDA）受体拮抗剂的神经保护特性与抗氧化功能性的结合，制备了一系列化合物。使用循环伏安法对这些化合物的氧化还原化学性质进行了评估，并将评估结果与两种标准生物检测方法（抑制脂质过氧化（硫代巴比妥酸反应物质检测法）和蓝宝石比色法）得出的自由基清除特性进行了比较。这些不同方法得出的结果基本一致。最有效的抗氧化剂是替代酚类，例如 Trolox。一系列嘧啶类化合物的抗氧化活性取决于三个氨基取代基的存在。
• Piperazine and homopiperazine derivatives, pharmaceutical compositions
  申请人：Gyogyszerkutato Intezet KFT

  公开号：US05380724A1

  公开（公告）日：1995-01-10

  This invention relates to novel compounds of the general formula (I) and the pharmaceutically acceptable acid addition salts thereof. In the general formula (I) ##STR1## wherein Lip, A.sup.1, A.sup.2, Het and n are defined as in the specification. The compounds of the general formula (I) inhibit the lipid peroxidation and therefore, they are useful for the treatment or prevention of diseases and conditions wherein the inhibition of lipid peroxidation is desirable.

  本发明涉及具有通式(I)的新颖化合物及其药学上可接受的酸加成盐。在通式(I)中，其中Lip、A1、A2、Het和n如说明书中所定义。通式(I)的化合物抑制脂质过氧化，因此，它们可用于治疗或预防需要抑制脂质过氧化的疾病和状况。
• Synthesis of radioactive and stable isotope labeled tirilazad mesylate
  作者：W. T. Stolle、J. A. Easter、E. H. Chew、J. P. McGrath、J. R. Palmer、R. S. P. Hsi

  DOI：10.1002/jlcr.2580341208

  日期：1994.12

  Tirilazad mesylate, 21-[4-(2,6-di-1-pyrrolidinyl-4-pyrimidinyl)-1-piperazinyl]-16α-methyl-pregna-1,4,9(11)-triene-3,20-dione monomethanesulfonate, is a potent lipid peroxidation inhibitor capable of suppressing progression of tissue damage caused by trauma or ischemia. Several isotopically labeled versions of the compound have been synthesized for conducting in vitro and in vivo metabolic transformations of this experimental drug. These include labeling with carbon-14 at the 16α-methyl group of the steroid portion of the molecule, or at the C-2 position of the pyrimidine ring; also with deuterium at the steroid 16α-methyl group, and/or with carbon-13 at C-2, C-4, and C-6, and with nitrogen-15 at N-1 and N-3 of the pyrimidine ring.

  Tirilazad美克酸盐，21-[4-(2,6-二（1-吡咯烷基）-4-嘧啶基）-1-哌嗪基]-16α-甲基-孕-1,4,9(11)-三烯-3,20-二酮单甲烷磺酸盐，是一种有效的脂质过氧化抑制剂，能够抑制由创伤或缺血引起的组织损伤进展。已经合成了几种同位素标记的该化合物用于进行该实验药物的体外和体内代谢转化。这些标记包括在分子类固醇部分的16α-甲基基团处用碳-14标记，或在嘧啶环的C-2位置；也包括在类固醇的16α-甲基基团处用氘标记，以及在C-2、C-4和C-6处用碳-13标记，和在嘧啶环的N-1与N-3处用氮-15标记。
• Pharmaceutically active amines
  申请人：Upjohn

  公开号：US05120843A1

  公开（公告）日：1992-06-09

  The aromatic amines (I), alkyl amines (II), bicyclic amines (III). ##STR1## cycloalkyl amines (IV), aromatic bicyclic amines (V), hydroquinone amines (VI), quinone amines (VII), amino-ethers (VIII) and bicyclic amino ethers (IX) are useful as pharmaceutical agents for treating a number of conditions including spinal trauma, mild and/or moderate to severe head injury, etc. Also disclosed is a method of treatment using the 3,4-dihydrobenzopyrans (XI).

  芳香胺（I），烷基胺（II），双环胺（III），环烷基胺（IV），芳香双环胺（V），氢醌胺（VI），醌胺（VII），氨基醚（VIII）和双环氨基醚（IX）可用作治疗多种疾病的药物，包括脊椎创伤、轻微和/或中度至严重头部损伤等。还公开了一种使用3,4-二氢苯并吡喯（XI）的治疗方法。