ethyl 4-<4-(4-fluorophenyl)-1-piperazinyl>butyrate | 130933-88-9

• 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-<4-(4-fluorophenyl)-1-piperazinyl>butyrate
• 英文别名: ethyl 4-[4-(4-fluorophenyl)piperazin-1-yl]butanoate；ethyl 4-(4-(4-fluorophenyl)piperazin-1-yl)-n-butyrate
• CAS: 130933-88-9
• 化学式: C₁₆H₂₃FN₂O₂
• 分子量: 294.369
• InChiKey: SQNIPLAAKKYGBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-<4-(4-fluorophenyl)-1-piperazinyl>butyrate 在 sodium hydroxide 、 sodium periodate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (6aR^*,10aR^*,11R^*)-11-<<4-<4-(4-fluorophenyl)-1-piperazinyl>butyryl>amino>-6,6a,7,8,9,10,10a,11-octahydrodibenzothiepin 5-oxide
  参考文献：
  名称：

  A new class of calcium antagonists. Synthesis and biological activity of 11-[(.omega.-aminoalkanoyl)amino]-6,6a,7,8,9,10,10a,11-octahydrodibenzo[b,e]thiepin derivatives

  摘要：

  A series of 11-[(omega-aminoalkanoyl)amino]-6,6a,7,8,9,10,10a,11?? -octahydrodibenzo[b,e]thiepin derivatives were prepared and found to be a structurally new class of calcium antagonists. The structure-activity relationship studies indicated that the optimum was (6aR*, 10aR*, 11R*)-11-[[4-[4-(4-fluorophenyl)-1-piperazinyl]butyryl]amino]-6,6a7,8,9,10,10a,11-octahydrodibenzo[b,e]thiepin (31, pA2 8.16), which was superior to diltiazem (pA2 7.42) in calcium antagonistic activity. Compound 31 showed antihypertensive activity in anesthetized rats, without a significant effect on the heart rate. It had also antianginal effects in vasopressin-induced ST-depression and methacholine-induced ST-elevation testings in rats. These potencies of 31 were essentially equal to those of diltiazem.

  DOI：

  10.1021/jm00106a019
• 作为产物：
  描述：

  4-溴丁酸乙酯 、 1-(4-氟苯基)哌嗪 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 生成 ethyl 4-<4-(4-fluorophenyl)-1-piperazinyl>butyrate
  参考文献：
  名称：

  作为5-HT7受体配体的新型喹唑啉酮衍生物。

  摘要：

  5-HT（7）受体拮抗剂在动物模型中产生了抗抑郁样作用，并且5-HT（7）受体参与了其他病理生理机制，例如温度调节，学习和记忆以及睡眠，这一点已被各种研究重点介绍。作为我们发现新型5-HT（7）受体拮抗剂的工作之一，我们在此报告喹唑啉酮文库1的5-HT（7）受体的合成和结合亲和力，该库设计有各种取代基（X，Y，R（1）和R（2））在芳香环上和不同的碳链长度。合成了喹唑啉酮文库1的总共85种化合物，并通过放射性配体结合测定法对5-HT（7）受体获得了所有合成化合物的结合亲和力。在85种化合物中，24种化合物显示出非常好的结合亲和力，IC（50）值低于100 nM。IC（50）值低于100 nM的化合物主要具有o-OMe或o-OEt作为R（2）取代基。具有最佳结合亲和力的化合物为1-68，其中IC（50）值为12 nM。在体内动物研究中，某些合成的化合物在小鼠的强迫游泳试验中确实具有抗抑郁活性。

  DOI：

  10.1016/j.bmc.2007.11.049

文献信息

• Solventless microwave assisted protocol for synthesis of arylalkylpiperazines using Cs-base
  作者：Alain Gamal Giuglio-Tonolo、Thierry Terme、Patrice Vanelle

  DOI：10.1039/b812801d

  日期：——

  A series of some arylalkylpiperazines was prepared in good yields under microwave irradiation in dry media conditions using CsOH with high chemo- and regioselectivity.

  在干燥介质条件下，利用CsOH在微波辐射下制备了一系列取代芳基烷基哌嗪，获得了较高的产率，并且具有良好的化学选择性和区域选择性。
• Fused heterocyclic compounds and pharmaceutical applications thereof
  申请人：Yoshitomi Pharmaceutical Industries, Ltd.

  公开号：US06187774B1

  公开（公告）日：2001-02-13

  The present invention relates to a fused heterocyclic compound of the formula (I) wherein each symbol is as defined in the specification, an optical isomer thereof, a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing a compound of the formula (I), an optical isomer thereof or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive, and a medicament containing a compound of the formula (I), an optical isomer thereof or a pharmaceutically acceptable salt thereof. The compound of the present invention is a useful antipsychotic agent effective not only for positive symptoms centering on hallucination and delusion characteristic of the acute stage of schizophrenia, but also negative symptoms of apathy, abulia and autism. The inventive compound is expected to make a highly safe antipsychotic agent associated with less side effects, such as extrapyramidal symptoms and endocrine disturbance, which are observed when a conventional antipsychotic agent having a D2 receptor blocking action is administered. Therefore, the inventive compound can be used as a therapeutic agent for the diseases such as schizophrenia.

  本发明涉及一种融合杂环化合物，其化学式为(I)，其中每个符号如规范中定义的一个光学异构体，一个药学上可接受的盐，含有化合物(I)、其光学异构体或药学上可接受的盐的药物组合物，以及药学上可接受的添加剂和含有化合物(I)、其光学异构体或药学上可接受的盐的药物。本发明化合物是一种有用的抗精神病药物，不仅对于中心于幻觉和妄想的阳性症状，也对于无动力、无意志和自闭症等阴性症状有效。本发明化合物预计成为一种高度安全的抗精神病药物，与传统的具有D2受体阻滞作用的抗精神病药物相比，其副作用较少，如锥体外系症状和内分泌紊乱。因此，本发明化合物可用作治疗精神分裂症等疾病的治疗剂。
• FUSED HETEROCYCLIC COMPOUNDS AND PHARMACEUTICAL APPLICATIONS THEREOF
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0885883A1

  公开（公告）日：1998-12-23

  The present invention relates to a fused heterocyclic compound of the formula (I) wherein each symbol is as defined in the specification, an optical isomer thereof, a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing a compound of the formula (I), an optical isomer thereof or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive, and a medicament containing a compound of the formula (I), an optical isomer thereof or a pharmaceutically acceptable salt thereof. The compound of the present invention is a useful antipsychotic agent effective not only for positive symptoms centering on hallucination and delusion characteristic of the acute stage of schizophrenia, but also negative symptoms of apathy, abulia and autism. The inventive compound is expected to make a highly safe antipsychotic agent associated with less side effects, such as extrapyramidal symptoms and endocrine disturbance, which are observed when a conventional antipsychotic agent having a D2 receptor blocking action is administered. Therefore, the inventive compound can be used as a therapeutic agent for the diseases such as schizophrenia.

  本发明涉及式（I）的融合杂环化合物、其光学异构体、其药用盐、含有式（I）化合物、其光学异构体或其药用组合物的药物组合物。 其中各符号如说明书中所定义；其光学异构体；其药学上可接受的盐；含有式（I）化合物、其光学异构体或其药学上可接受的盐和药学上可接受的添加剂的药物组合物；以及含有式（I）化合物、其光学异构体或其药学上可接受的盐的药物。本发明的化合物是一种有用的抗精神病药物，不仅对精神分裂症急性期特有的以幻觉和妄想为中心的阳性症状有效，而且对冷漠、乏力和自闭等阴性症状也有效。本发明化合物有望成为一种高度安全的抗精神病药物，其副作用较小，如锥体外系症状和内分泌紊乱，这些副作用在使用具有 D2 受体阻断作用的传统抗精神病药物时会出现。因此，本发明化合物可用作精神分裂症等疾病的治疗药物。
• KUROKAWA, MIKIO;SATO, FUMINORI;HATANO, NAONOBU;HONDA, YAYOI;UNO, HITOSHI, J. MED. CHEM. , 34,(1991) N, C. 593-599
  作者：KUROKAWA, MIKIO、SATO, FUMINORI、HATANO, NAONOBU、HONDA, YAYOI、UNO, HITOSHI

  DOI：——

  日期：——
• US6187774B1
  申请人：——

  公开号：US6187774B1

  公开（公告）日：2001-02-13