4-<(4-phenylpyridazinyl)piperazin-1-yl>-1,1-ethylenedioxy-1-(4-fluorophenyl)butane | 161331-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-<(4-phenylpyridazinyl)piperazin-1-yl>-1,1-ethylenedioxy-1-(4-fluorophenyl)butane
• 英文别名: 3-[4-[3-[2-(4-Fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperazin-1-yl]-6-phenylpyridazine
• CAS: 161331-20-0
• 化学式: C₂₆H₂₉FN₄O₂
• 分子量: 448.54
• InChiKey: UOVGTKULNMLISR-UHFFFAOYSA-N

物化性质

• 沸点：
  637.3±55.0 °C(predicted)
• 密度：
  1.204±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  50.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-<(4-phenylpyridazinyl)piperazin-1-yl>-1,1-ethylenedioxy-1-(4-fluorophenyl)butane 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以68%的产率得到3-<4-<3-(p-fluorobenzoyl)>-1-propylpiperazin-1-yl>-6-phenylpyridazine
  参考文献：
  名称：

  Pyridazine derivatives XII. Synthesis and antipsychotic-antidepressant activity of some butyrophenone derivatives of 6-phenylpyridazine

  摘要：

  We have synthesized several 3-amino-6-phenyl pyridazines in which the amino substituent is a linear butyrophenone moiety (compounds 8 and 10), a cyclic butyrophenone moiety (compound 3), or a phenylpiperazine fragment (compound 2). Compound 8 potently inhibited [H-3]spiperone binding to striatal D-2 receptors and [H-3]SCH 23390 binding to striatal D-1 receptors (K-i in the nanomolar range but lower than that of haloperidol). Compounds 3, 2 and 10 showed no affinity for dopamine (DA) receptors. Only 2 compounds (3 and 8) inhibited [H-3]ketanserin binding to cortical 5-HT2A receptors; compound 8 strongly inhibited binding with a K-i similar to that of methysergide, while binding was only weakly inhibited by compound 3. The DA and 5-HT2A antagonist. activity of compound 8 was evaluated in vivo and in vitro. The results in standard screening tests indicate that this compound possesses neuroleptic activity. However, in contrast to haloperidol, compound 8 did not modify DA and its metabolite levels in rat striatum, or induce catalepsy. It inhibited serotonin-induced contractions in endothelium-stripped aorta with a pA(2) of 8.26 and did not affect reserpine induced palpebral ptosis, indicating that it does not have antidepressant activity; compound 10, however, showed slight activity in this test.

  DOI：

  10.1016/0223-5234(94)90106-6
• 作为产物：
  描述：

  3-氯-6-苯基哒嗪 在 sodium carbonate 、 potassium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 20.0h， 生成 4-<(4-phenylpyridazinyl)piperazin-1-yl>-1,1-ethylenedioxy-1-(4-fluorophenyl)butane
  参考文献：
  名称：

  Pyridazine derivatives XII. Synthesis and antipsychotic-antidepressant activity of some butyrophenone derivatives of 6-phenylpyridazine

  摘要：

  We have synthesized several 3-amino-6-phenyl pyridazines in which the amino substituent is a linear butyrophenone moiety (compounds 8 and 10), a cyclic butyrophenone moiety (compound 3), or a phenylpiperazine fragment (compound 2). Compound 8 potently inhibited [H-3]spiperone binding to striatal D-2 receptors and [H-3]SCH 23390 binding to striatal D-1 receptors (K-i in the nanomolar range but lower than that of haloperidol). Compounds 3, 2 and 10 showed no affinity for dopamine (DA) receptors. Only 2 compounds (3 and 8) inhibited [H-3]ketanserin binding to cortical 5-HT2A receptors; compound 8 strongly inhibited binding with a K-i similar to that of methysergide, while binding was only weakly inhibited by compound 3. The DA and 5-HT2A antagonist. activity of compound 8 was evaluated in vivo and in vitro. The results in standard screening tests indicate that this compound possesses neuroleptic activity. However, in contrast to haloperidol, compound 8 did not modify DA and its metabolite levels in rat striatum, or induce catalepsy. It inhibited serotonin-induced contractions in endothelium-stripped aorta with a pA(2) of 8.26 and did not affect reserpine induced palpebral ptosis, indicating that it does not have antidepressant activity; compound 10, however, showed slight activity in this test.

  DOI：

  10.1016/0223-5234(94)90106-6

文献信息

• Pyridazine derivatives XII. Synthesis and antipsychotic-antidepressant activity of some butyrophenone derivatives of 6-phenylpyridazine
  作者：M CASTRO、E ROSA、J AOSUNA、T GARCIAFERREIRO、M LOZA、M CADAVID、J FONTENLA、C FMASAGUER、J CID、E RAVINA

  DOI：10.1016/0223-5234(94)90106-6

  日期：——

  We have synthesized several 3-amino-6-phenyl pyridazines in which the amino substituent is a linear butyrophenone moiety (compounds 8 and 10), a cyclic butyrophenone moiety (compound 3), or a phenylpiperazine fragment (compound 2). Compound 8 potently inhibited [H-3]spiperone binding to striatal D-2 receptors and [H-3]SCH 23390 binding to striatal D-1 receptors (K-i in the nanomolar range but lower than that of haloperidol). Compounds 3, 2 and 10 showed no affinity for dopamine (DA) receptors. Only 2 compounds (3 and 8) inhibited [H-3]ketanserin binding to cortical 5-HT2A receptors; compound 8 strongly inhibited binding with a K-i similar to that of methysergide, while binding was only weakly inhibited by compound 3. The DA and 5-HT2A antagonist. activity of compound 8 was evaluated in vivo and in vitro. The results in standard screening tests indicate that this compound possesses neuroleptic activity. However, in contrast to haloperidol, compound 8 did not modify DA and its metabolite levels in rat striatum, or induce catalepsy. It inhibited serotonin-induced contractions in endothelium-stripped aorta with a pA(2) of 8.26 and did not affect reserpine induced palpebral ptosis, indicating that it does not have antidepressant activity; compound 10, however, showed slight activity in this test.