4-(5-chloro-pyrimidin-2-yl)-piperazine-1-carboxylic acid ethyl ester | 99931-84-7

• 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: 4-(5-chloro-pyrimidin-2-yl)-piperazine-1-carboxylic acid ethyl ester
• 英文别名: 4-(5-Chlor-pyrimidin-2-yl)-piperazin-1-carbonsaeure-aethylester；Ethyl 4-(5-chloro-2-pyrimidinyl)-1-piperazinecarboxylate；ethyl 4-(5-chloropyrimidin-2-yl)piperazine-1-carboxylate
• CAS: 99931-84-7
• 化学式: C₁₁H₁₅ClN₄O₂
• 分子量: 270.719
• InChiKey: QHJYVWGHBDUGGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  4-(5-chloro-pyrimidin-2-yl)-piperazine-1-carboxylic acid ethyl ester 生成 5-氟-2-(1-哌嗪基)-嘧啶
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 4-(2-pirymidinyl)-1-piperazinecarboxylate 在 盐酸 、 氯 作用下， 反应 0.25h， 以54%的产率得到4-(5-chloro-pyrimidin-2-yl)-piperazine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and biological characterization of .alpha.-(4-fluorophenyl)-4-(5-fluoro-2-pyrimidinyl)-1-piperazinebutanol and analogs as potential atypical antipsychotic agents

  摘要：

  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.

  DOI：

  10.1021/jm00102a002

文献信息

• ——
  作者：YEVICH J. P.、 LOBECK W. G., JR.

  DOI：——

  日期：——
• 2-Pyrimidinyl-l-piperazin-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
  申请人：Troponwerke GmbH & Co. KG

  公开号：EP0129128B1

  公开（公告）日：1990-11-22
• US4818756A
  申请人：——

  公开号：US4818756A

  公开（公告）日：1989-04-04
• US4988809A
  申请人：——

  公开号：US4988809A

  公开（公告）日：1991-01-29
• US4937343A
  申请人：——

  公开号：US4937343A

  公开（公告）日：1990-06-26