ethyl 4-(2-pirymidinyl)-1-piperazinecarboxylate | 99931-83-6

• 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: ethyl 4-(2-pirymidinyl)-1-piperazinecarboxylate
• 英文别名: 1-(ethoxycarbonyl)-4-(2-pyrimidinyl)piperazine；4-pyrimidin-2-yl-piperazine-1-carboxylic acid ethyl ester；4-Pyrimidin-2-yl-piperazin-1-carbonsaeure-aethylester；N-carbethoxy-1-pyrimidin-2-ylpiperazine；Ethyl 4-(pyrimidin-2-yl)piperazine-1-carboxylate；ethyl 4-pyrimidin-2-ylpiperazine-1-carboxylate
• CAS: 99931-83-6
• 化学式: C₁₁H₁₆N₄O₂
• mdl: MFCD02571455
• 分子量: 236.274
• InChiKey: PXNBCBKGSZGMFC-UHFFFAOYSA-N

物化性质

• 熔点：
  67.5-69 °C
• 沸点：
  397.4±52.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-(2-pirymidinyl)-1-piperazinecarboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以82%的产率得到1-(2-嘧啶基)哌嗪
  参考文献：
  名称：

  Valenta, Vladimir; Holubek, Jiri; Svatek, Emil, Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 9, p. 2304 - 2316

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯嘧啶 、 1-哌嗪羧酸乙酯盐酸盐 在 碳酸氢钠 作用下， 生成 ethyl 4-(2-pirymidinyl)-1-piperazinecarboxylate
  参考文献：
  名称：

  Piperazines. II. 1-Heterocyclicpiperazines and 1-Hetero-Cyclic-4-Carbethoxypiperazines

  摘要：

  DOI：

  10.1021/jo50017a004

文献信息

• Antipsychotic 1-fluorophenylbutyl-4-(2-pyrimidinyl)piperazine derivatives
  申请人：Bristol-Myers Company

  公开号：US04605655A1

  公开（公告）日：1986-08-12

  Disubstituted N,N-piperazinyl derivatives are disclosed wherein one substituent is a pyrimidin-2-yl ring and the other is a 4 carbon chain attached to a p-fluorophenyl ring at the terminal carbon. The terminal carbon of this butylene chain is also bonded to an oxygen atom as part of a carbonyl, carbinol, or ketal functionality. These compounds possess psychotropic properties, particularly atypical antipsychotic activity of good duration. By virtue of pre-clinical pharmacological testing, these compounds appear useful as potential antipsychotic agents which lack the typical movement disorder side-effects of standard antipsychotic agents.

  二取代N,N-哌嗪基衍生物被披露，其中一个取代基是嘧啶-2-基环，另一个是连接到对氟苯基环的末端碳上的4碳链。这个丁二烯链的末端碳也与一个氧原子结合，作为羰基、醇基或缩醛功能团的一部分。这些化合物具有精神药理特性，特别是良好持续时间的非典型抗精神病活性。通过临床前药理学测试，这些化合物似乎有望作为潜在的抗精神病药物，而不具有标准抗精神病药物的典型运动障碍副作用。
• Synthesis and biological characterization of .alpha.-(4-fluorophenyl)-4-(5-fluoro-2-pyrimidinyl)-1-piperazinebutanol and analogs as potential atypical antipsychotic agents
  作者：Joseph P. Yevich、James S. New、Walter G. Lobeck、Pierre Dextraze、Edith Bernstein、Duncan P. Taylor、Frank D. Yocca、Michael S. Eison、Davis L. Temple

  DOI：10.1021/jm00102a002

  日期：1992.11

  A series of 1-(pyrimidin-2-yl)piperazine derivatives were prepared and evaluated in receptor binding assays and in in vivo behavioral paradigms as potential atypical antipsychotic agents. Compound 16 (BMS 181100 (formerly BMY 14802)) emerged as the lead compound from within the series on the basis of its good activity and duration of action in the inhibition of both conditioned avoidance responding and apomorphine-induced stereotopy in the rat. Compound 16 not only failed to induce catalepsy in the rat but was quite effective in reversing the cataleptic effect of neuroleptic agents, thus indicating a low propensity for causing extrapyramidal side effects. In comparison to reference antipsychotic agents, 16 appeared to be less sedating and was relatively weaker in causing muscle incoordination. The compound was essentially inactive in binding to dopamine D2 receptors and its chronic administration to rats did not result in dopamine receptor supersensitivity. It exhibited modest to weak affinity for 5-HT1A and alpha1 receptors but was found to be a fairly potent ligand for sigma binding sites (IC50 vs (+)-[H-3]-3-PPP = 112 nM). Although the resolved enantiomers of racemic 16 did not show dramatic differences from racemate or from each other in most tests, the R(+) enantiomer was up to 11-fold more potent than its antipode in binding to sigma sites. Several studies have indicated that 16 may be a limbic-selective agent which may modulate dopaminergic activity by an indirect mechanism. The compound has been selected for clinical evaluation in the treatment of psychosis.
• VALENTA, VLADIMIR;HOLUBEK, JIRI;SVATEK, EMIL;PROTIVA, MIROSLAV, COLLECT. CZECHOSL. CHEM. COMMUN., 55,(1990) N, C. 2304-2316
  作者：VALENTA, VLADIMIR、HOLUBEK, JIRI、SVATEK, EMIL、PROTIVA, MIROSLAV

  DOI：——

  日期：——
• US4605655A
  申请人：——

  公开号：US4605655A

  公开（公告）日：1986-08-12
• Piperazines. II. 1-Heterocyclicpiperazines and 1-Hetero-Cyclic-4-Carbethoxypiperazines
  作者：K. L. Howard、H. W. Stewart、E. A. Conroy、J. J. Denton

  DOI：10.1021/jo50017a004

  日期：1953.11