5-(哌嗪-1-基)戊酸甲酯 | 62522-30-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 5-(哌嗪-1-基)戊酸甲酯
• 英文名称: 1-(4-methoxycarbonylbutyl)piperazine
• 英文别名: methyl 5-piperazinepentanoate；5-piperazin-1-yl-pentanoic acid methyl ester；Methyl 5-(piperazin-1-YL)pentanoate；methyl 5-piperazin-1-ylpentanoate
• CAS: 62522-30-9
• 化学式: C₁₀H₂₀N₂O₂
• 分子量: 200.281
• InChiKey: WAYDSYRQCUKMDS-UHFFFAOYSA-N

物化性质

• 沸点：
  284.3±25.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(哌嗪-1-基)戊酸甲酯 在 甲醇 、 草酰氯 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-[3β-hydroxy-2α-propargyl-lup-20(29)-en-28-oyl]-5-piperazine-pentanoic acid
  参考文献：
  名称：

  点击化学辅助合成新型 C-2 三唑连接的桦木酸偶联物与叠氮胸苷作为可能的抗 HIV 药物

  摘要：

  描述了一种基于 Cu 催化的炔烃和叠氮化物之间的 1,3-环加成反应的 C-2 三唑连接生物共轭物与 3'-叠氮基-3'脱氧胸苷 (AZT) 的新合成方法。将 AZT-桦木酸杂化分子作为潜在的抗 HIV 药物的拟议策略使得改变三萜部分中的 C-3 和 C-28 药效团成为可能。通过点击反应成功合成了C-2炔丙基取代的桦木酸及其在C-3和/或C-28位具有侧链的单或双功能衍生物。

  DOI：

  10.24820/ark.5550190.p010.632
• 作为产物：
  描述：

  哌嗪 、 5-溴戊酸甲酯 以 甲苯 为溶剂， 反应 4.0h， 以42%的产率得到5-(哌嗪-1-基)戊酸甲酯
  参考文献：
  名称：

  Anti-AIDS Agents 90. Novel C-28 Modified Bevirimat Analogues as Potent HIV Maturation Inhibitors

  摘要：

  In a continuing study of bevirimat (2), the anti-HIV-maturation clinical trials agent, 28 new betulinic acid (BA, 1) derivatives were designed and synthesized. Among these compounds, 17, with a C-28 MEM ester moiety, and 22, with a C-28 ethyl hexanoate, increased the anti-HIV replication activity compared with 2 by 2-fold while compounds 40, 41, 48, and 49, with C-28 piperazine or piperidine amide substitutions, increased the activity by 3- to 15-fold. The best new compound, 41, exhibited an anti-HIV IC50 of 0.0059 mu M compared with 0.087 mu M antimaturation effects, as confirmed by TZM-bl assay, in blocking the HIV replication. The results suggest that proper C-28 substitutions can further enhance the antimaturation activity of 2 without any antientry effects. Thus, 41 may serve as a promising new lead for development of anti-AIDS clinical trial candidates.

  DOI：

  10.1021/jm301040s

文献信息

• Small Molecules Simultaneously Inhibiting p53-Murine Double Minute 2 (MDM2) Interaction and Histone Deacetylases (HDACs): Discovery of Novel Multitargeting Antitumor Agents
  作者：Shipeng He、Guoqiang Dong、Shanchao Wu、Kun Fang、Zhenyuan Miao、Wei Wang、Chunquan Sheng

  DOI：10.1021/acs.jmedchem.8b00664

  日期：2018.8.23

  interaction and histone deacetylases (HDACs) are important targets in antitumor drug development. Inspired by the synergistic effects between MDM2 and HDACs, the first MDM2/HDACs dual inhibitors were identified, which showed excellent activities against both targets. In particular, compound 14d was proven to be a potent and orally active MDM2/HDAC dual inhibitor, whose antitumor mechanisms were validated in

  p53-小鼠双分钟2（MDM2）相互作用和组蛋白脱乙酰基酶（HDACs）是抗肿瘤药物开发中的重要目标。受MDM2和HDAC之间的协同作用的启发，确定了首批MDM2 / HDACs双重抑制剂，它们对两个靶标均表现出出色的活性。特别是，化合物14d被证明是一种有效且具有口服活性的MDM2 / HDAC双重抑制剂，其抗肿瘤机制已在癌细胞中得到验证。化合物14d在A549异种移植模型中显示出优异的体内抗肿瘤能力，为开发新型抗肿瘤剂提供了有希望的先导化合物。同样，这项概念验证研究为多靶点抗肿瘤药物发现提供了一种新颖而有效的策略。
• Radioimmunoassay for Psychotropic Drugs III: Synthesis and Properties of Haptens for Trifluoperazine and Fluphenazine
  作者：E.M. Hawes、H.U. Shetty、J.K. Cooper、G. Rauw、G. McKay、K.K. Midha

  DOI：10.1002/jps.2600730226

  日期：1984.2

  development of radioimmunoassay procedures for trifluoperazine and fluphenazine, three haptens, N-(2-carboxyethyl)desmethyltrifluoperazine, N-(4-carboxybutyl)desmethyltrifluoperazine, and 10-[3-(4-carboxyethylpiperazinyl)-3-oxopropyl]-2-trifluoromethyl-+ ++10H- phenothiazine, were synthesized and characterized. Each hapten was coupled to bovine serum albumin, and the number of hapten residues per mole

  为了开发三氟哌嗪和氟奋乃静的放射免疫测定方法，使用了三个半抗原，N-（2-羧乙基）去甲基三氟哌嗪，N-（4-羧丁基）去甲基三氟哌嗪和10- [3-（4-羧乙基哌嗪基）-3-氧丙基] -2合成并表征了-三氟甲基-++++ 10H-吩噻嗪。将每个半抗原与牛血清白蛋白偶联，并通过UV分光光度法计算每摩尔牛血清白蛋白的半抗原残基数。在兔体内开发了针对每种半抗原蛋白偶联物的抗体，并通过评估其与the化药物的结合特性来检查抗血清的效价。
• Discovery of a Novel G-Quadruplex and Histone Deacetylase (HDAC) Dual-Targeting Agent for the Treatment of Triple-Negative Breast Cancer
  作者：Xin-Chen Jiang、Fang-Hai Tu、Li-Yuan Wei、Bo-Zheng Wang、Hao Yuan、Jing-Mei Yuan、Yong Rao、Shi-Liang Huang、Qing-Jiang Li、Tian-Miao Ou、Hong-Gen Wang、Jia-Heng Tan、Shuo-Bin Chen、Zhi-Shu Huang

  DOI：10.1021/acs.jmedchem.2c01058

  日期：2022.9.22
• Anti-AIDS Agents 90. Novel C-28 Modified Bevirimat Analogues as Potent HIV Maturation Inhibitors
  作者：Keduo Qian、Ibrahim D. Bori、Chin-Ho Chen、Li Huang、Kuo-Hsiung Lee

  DOI：10.1021/jm301040s

  日期：2012.9.27

  In a continuing study of bevirimat (2), the anti-HIV-maturation clinical trials agent, 28 new betulinic acid (BA, 1) derivatives were designed and synthesized. Among these compounds, 17, with a C-28 MEM ester moiety, and 22, with a C-28 ethyl hexanoate, increased the anti-HIV replication activity compared with 2 by 2-fold while compounds 40, 41, 48, and 49, with C-28 piperazine or piperidine amide substitutions, increased the activity by 3- to 15-fold. The best new compound, 41, exhibited an anti-HIV IC50 of 0.0059 mu M compared with 0.087 mu M antimaturation effects, as confirmed by TZM-bl assay, in blocking the HIV replication. The results suggest that proper C-28 substitutions can further enhance the antimaturation activity of 2 without any antientry effects. Thus, 41 may serve as a promising new lead for development of anti-AIDS clinical trial candidates.
• Click chemistry-assisted synthesis of novel C-2 triazole-linked betulinic acid conjugates with azidothymidine as potential anti-HIV agents
  作者：Anna Yu. Spivak、Darya A. Nedopekina、Zulfiya R. Galimshina、Rezeda R. Khalitova、Zarema R. Sadretdinova、Rinat R. Gubaidullin、Victor N. Odinokov

  DOI：10.24820/ark.5550190.p010.632

  日期：——

  approach to C-2 triazole-linked bioconjugates of lupane triterpenoids with 3’-azido-3’deoxythymidine (AZT) based on Cu-catalyzed 1,3-cycloaddition between alkynes and azides is described. The proposed strategy towards AZT–betulinic acid hybrid molecules as potential anti-HIV agents makes it possible to vary the C-3 and C-28 pharmacophores in triterpene moieties. The C-2 propargyl-substituted betulinic acid

  描述了一种基于 Cu 催化的炔烃和叠氮化物之间的 1,3-环加成反应的 C-2 三唑连接生物共轭物与 3'-叠氮基-3'脱氧胸苷 (AZT) 的新合成方法。将 AZT-桦木酸杂化分子作为潜在的抗 HIV 药物的拟议策略使得改变三萜部分中的 C-3 和 C-28 药效团成为可能。通过点击反应成功合成了C-2炔丙基取代的桦木酸及其在C-3和/或C-28位具有侧链的单或双功能衍生物。