3-phenyl-1-(4-(piperazin-1-yl)phenyl)prop-2-en-1-one | 956699-70-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-phenyl-1-(4-(piperazin-1-yl)phenyl)prop-2-en-1-one
• 英文别名: (E)-3-phenyl-1-(4-piperazin-1-ylphenyl)prop-2-en-1-one
• CAS: 956699-70-0
• 化学式: C₁₉H₂₀N₂O
• 分子量: 292.381
• InChiKey: RHOMNGQJUHXEJC-IZZDOVSWSA-N

物化性质

• 熔点：
  48-49 °C
• 沸点：
  505.7±50.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对叔丁基苯磺酰氯 、 3-phenyl-1-(4-(piperazin-1-yl)phenyl)prop-2-en-1-one 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以69%的产率得到(E)-1-(4-(4-((4-(tert-butyl)phenyl)sulfonyl)piperazin-1-yl)phenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  查尔酮衍生物作为抗炎剂的设计，合成，生物学评估和分子对接

  摘要：

  在这项研究中，合成了两个系列的35个新的查尔酮衍生物，它们分别包含芳基-哌嗪或芳基-磺酰基-哌嗪片段，并通过1 H，13 C和ESI-MS对其结构进行了表征。在体内和体外的目标化合物的抗炎活性通过使用经典评价对二甲苯诱导的小鼠耳肿胀模型和ELISA测定。此外，在COX-2（4PH9）中进行了对接研究。在体内抗炎试验表明，大多数目标化合物均显示出显着的抗炎活性。对接结果表明，化合物的抗炎活性与其对接结果相关。特别是，化合物6o在体内表现出最强的抗炎活性，最低的对接分数为-17.4 kcal / mol，并且可以在体外以剂量依赖的方式显着抑制LPS诱导的IL-6和TNF-α的释放。。

  DOI：

  10.1016/j.bmcl.2016.12.008
• 作为产物：
  描述：

  苯甲醛 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 3-phenyl-1-(4-(piperazin-1-yl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  查尔酮衍生物作为抗炎剂的设计，合成，生物学评估和分子对接

  摘要：

  在这项研究中，合成了两个系列的35个新的查尔酮衍生物，它们分别包含芳基-哌嗪或芳基-磺酰基-哌嗪片段，并通过1 H，13 C和ESI-MS对其结构进行了表征。在体内和体外的目标化合物的抗炎活性通过使用经典评价对二甲苯诱导的小鼠耳肿胀模型和ELISA测定。此外，在COX-2（4PH9）中进行了对接研究。在体内抗炎试验表明，大多数目标化合物均显示出显着的抗炎活性。对接结果表明，化合物的抗炎活性与其对接结果相关。特别是，化合物6o在体内表现出最强的抗炎活性，最低的对接分数为-17.4 kcal / mol，并且可以在体外以剂量依赖的方式显着抑制LPS诱导的IL-6和TNF-α的释放。。

  DOI：

  10.1016/j.bmcl.2016.12.008

文献信息

• 查尔酮衍生物及其制备方法与应用
  申请人：广西大学

  公开号：CN106083763A

  公开（公告）日：2016-11-09

  本发明公开了一种查尔酮衍生物，包括芳基哌嗪、芳基磺酰基哌嗪类苦参碱衍生物，还公开了该衍生物的制备方法和在药物中的应用。
• Triarylpyridines: a versatile small molecule scaffold for G-quadruplex recognition
  作者：Zoë A. E. Waller、Pravin S. Shirude、Raphaël Rodriguez、Shankar Balasubramanian

  DOI：10.1039/b718854d

  日期：——

  The triarylpyridines are potent G-quadruplex ligands that are highly discriminating against duplex DNA and show promising selectivity between intramolecular quadruplexes.

  三芳基吡啶是强效的 G-四链配体，对双链 DNA 有很强的辨别能力，并在分子内四链之间表现出良好的选择性。
• Antiproliferative activity of chalcones with basic functionalities
  作者：Xiaoling Liu、Mei-Lin Go

  DOI：10.1016/j.bmc.2007.07.042

  日期：2007.11

  A library of chalcones with different basic groups were synthesized and evaluated for antiproliferative activities against the human breast cancer (MCF 7) and colon cancer (HCT 116) cell lines. Structure-activity relationships were analyzed by projection methods (PCA/PLS) and multiple linear regression. Polar volume, hydrogen bonding features, HOMO energies, and charge on the carbon were found to be important factors. A basic group on either ring A or B of the chalcone led to a favourable increase in polar Volume, but when present on ring B, it increased HOMO energies and decreased the positive charge on the carbon, both of which led to lower activity. Several examples showed that final activity of the chalcone was influenced by compensatory interactions among these parameters. In general, a single basic group on ring A was associated with good activity. A notable exception was compound 1-123 which had basic groups on both rings A and B but Still maintained a good activity profile with IC50 < 10 PM and selectivity ratios >2.5. There was some evidence to show that structural differences in chalcones influenced not only activity but mechanism of action. Compounds 6-130 and 7-140 which had basic groups on ring A interfered with cell cycle progression, but the dibasic chalcone 1-123 had no effect. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and antimicrobial evaluation of new chalcones containing piperazine or 2,5-dichlorothiophene moiety
  作者：V. Tomar、G. Bhattacharjee、Kamaluddin、Ashok Kumar

  DOI：10.1016/j.bmcl.2007.08.021

  日期：2007.10

  Two new series of chalcones have been synthesized by reacting 1-(4-piperazin-1-yl-phenyl)ethanone and 1-(2,5-dichloro-3-thienyl)-1-ethanone with different substituted benzaldehydes in turn by Claisen-Schmidt condensation. The compounds have been characterized by IR, H-1 NMR spectral and microanalysis data. All the synthesized compounds have been evaluated for antimicrobial activity. Some of these derivatives are potentially active against Gram-positive bacteria, Stophylococcus aureus and Escherichia coli while the most potent compound (1) in this study showed MIC50 value of 2.22 mu g/mL against Candida albicans. (C) 2007 Elsevier Ltd. All rights reserved.
• Design, synthesis, biological evaluation, and molecular docking of chalcone derivatives as anti-inflammatory agents
  作者：Jingfen Li、Dong Li、Yiming Xu、Zhenbo Guo、Xu Liu、Hua Yang、Lichuan Wu、Lisheng Wang

  DOI：10.1016/j.bmcl.2016.12.008

  日期：2017.2

  two series of 35 new chalcone derivatives containing aryl-piperazine or aryl-sulfonyl-piperazine fragment were synthesized and their structures were characterized by 1H, 13C and ESI-MS. The in vivo and in vitro anti-inflammatory activities of target compounds were evaluated by using classical para-xylene-induced mice ear-swelling model and ELISA assays. Furthermore, docking studies were performed in COX-2

  在这项研究中，合成了两个系列的35个新的查尔酮衍生物，它们分别包含芳基-哌嗪或芳基-磺酰基-哌嗪片段，并通过1 H，13 C和ESI-MS对其结构进行了表征。在体内和体外的目标化合物的抗炎活性通过使用经典评价对二甲苯诱导的小鼠耳肿胀模型和ELISA测定。此外，在COX-2（4PH9）中进行了对接研究。在体内抗炎试验表明，大多数目标化合物均显示出显着的抗炎活性。对接结果表明，化合物的抗炎活性与其对接结果相关。特别是，化合物6o在体内表现出最强的抗炎活性，最低的对接分数为-17.4 kcal / mol，并且可以在体外以剂量依赖的方式显着抑制LPS诱导的IL-6和TNF-α的释放。。