3-(4-(2-甲氧基苯基)哌嗪-1-基)丙酸 | 732298-45-2

• 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: 3-(4-(2-甲氧基苯基)哌嗪-1-基)丙酸
• 英文名称: 3-(4-(2-methoxyphenyl)piperazin-1-yl)propanoic acid
• 英文别名: 3-[4-(2-methoxyphenyl)-1-piperazinyl]propionic acid；3-[4-(2-methoxyphenyl)piperazin-1-yl]propionic acid；3-[4-(2-Methoxyphenyl)piperazin-1-ium-1-yl]propanoate
• CAS: 732298-45-2
• 化学式: C₁₄H₂₀N₂O₃
• mdl: MFCD07397884
• 分子量: 264.324
• InChiKey: WQQWTUBIANMMPU-UHFFFAOYSA-N

物化性质

• 沸点：
  448.8±45.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  喜树碱 、 3-(4-(2-甲氧基苯基)哌嗪-1-基)丙酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以81.2%的产率得到
  参考文献：
  名称：

  Synthesis and antitumor activity of 20-O-linked nitrogen-based camptothecin ester derivatives

  摘要：

  A series of nitrogen-based 20S-hydroxyl camptothecin ester derivatives were prepared. 3-Aminopropionate of camptothecin was found more cytotoxic in vitro on several human tumor cell lines than 3-amidopropionate of camptothecin. Ester 16 showed best antitumor activity in vivo and in vitro in all esters we prepared. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.023
• 作为产物：
  描述：

  ethyl 3-(4-(2-methoxyphenyl)piperazin-1-yl)propanoate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-(4-(2-甲氧基苯基)哌嗪-1-基)丙酸
  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

• Compositions, Synthesis, and Methods of Using Quinolinone Based Atypical Antipsychotic Agents
  申请人：Bhat Laxminarayan

  公开号：US20080293736A1

  公开（公告）日：2008-11-27

  The present invention provides novel quinolinone derivatives which can be advantageously used for treating schizophrenia and related psychoses such as acute manic, bipolar disorder, autistic disorder, and depression.

  本发明提供了新型喹诺酮衍生物，可以有效用于治疗精神分裂症及相关精神病，如急性躁狂症、双相情感障碍、自闭症和抑郁症。
• Novel N-biphenyl-2-ylmethyl 2-methoxyphenylpiperazinylalkanamides as 5-HT7R antagonists for the treatment of depression
  作者：Youngjae Kim、Jinsung Tae、Kangho Lee、Hyewhon Rhim、Il Han Choo、Heeyeong Cho、Woo-Kyu Park、Gyochang Keum、Hyunah Choo

  DOI：10.1016/j.bmc.2014.07.026

  日期：2014.9

  5-HT7 receptor (5-HT7R) is a promising target for the treatment of depression and neuropathic pain. 5-HT7R antagonists exhibited antidepressant effects, while the agonists produced strong anti-hyperalgesic effects. In our efforts to discover selective 5-HT7R antagonists or agonists, N-biphenylylmethyl 2-methoxyphenylpiperazinylalkanamides 1 were designed, synthesized, and biologically evaluated against 5-HT7R. Among the synthesized compounds, N-2'-chlorobiphenylylmethyl 2-methoxyphenylpiperazinylpentanamide 1-8 showed the best binding affinity with a Ki value of 8.69nM and it was verified as a novel antagonist according to functional assays. The compound 1-8 was very selective over 5-HT1DR, 5-HT2AR, 5-HT3R, 5-HT5AR and 5-HT6R and moderately selective over 5-HT1AR, 5-HT1BR and 5-HT2CR. The novel 5-HT7R antagonist 1-8 exhibited an antidepressant effect at a dose of 25mg/kg in the forced swimming test in mice and showed a U-shaped dose-response curve which typically appears in 5-HT7R antagonists such as SB-269970 and lurasidone.
• Evaluation of anti-depressant effects of phthalazinone-based triple-acting small molecules against 5-HT2A, 5-HT2C, and the serotonin transporter
  作者：Jihye Kim、Eunji Cha、Woo Kyu Park、Hye Yeon Lee、Sang Min Lim、Hak Joong Kim、Ae Nim Pae

  DOI：10.1016/j.bmcl.2019.126882

  日期：2020.2

  Development of highly effective, safe, and fast-acting anti-depressants is urgently required for the treatment of major depressive disorder. It has been suggested that targeting 5-HT2A and 5-HT2C in addition to inhibition of serotonin reuptake may be beneficial in generating anti-depressant agents with better pharmacology and less adverse effects. We have developed phthalazinone-based compounds that potently bind to 5-HT2A, 5-HT2C, and the serotonin transporter. The representative compounds 11j and 11l displayed strong binding affinities against these targets, and showed favorable toxicity profiles as determined by hERG binding and CYP inhibition assays. Furthermore, these compounds presented promising anti-depressant effects comparable to fluoxetine and also synergistic effects with fluoxetine in forced swimming test, which implicates these compounds can be developed to help the treatment of major depressive disorder.
• COMPOSITIONS, SYNTHESIS, AND METHODS OF USING QUINOLINONE BASED ATYPICAL ANTIPSYCHOTIC AGENTS
  申请人：Reviva Pharmaceuticals, Inc.

  公开号：EP2162135A1

  公开（公告）日：2010-03-17
• INVERTEBRATE ACETYLCHOLINESTERASE INHIBITORS
  申请人：Pang Yuan-Ping

  公开号：US20080312091A1

  公开（公告）日：2008-12-18

  Methods for determining invertebrate- and insect-specific, such as mosquito-specific, residues of acetylcholinesterases are provided herein. The methods can be used to design pesticides and insecticides that are specific for the invertebrate or insect (e.g., mosquito) enzymes, resulting in reduced toxicity concerns for mammals. Compositions for inhibiting invertebrate and insect (e.g., mosquito) acetylcholinesterases and methods for preparing the same are also provided.