(E)-3-[4-(5-bromopentoxy)phenyl]-1-phenylprop-2-en-1-one | 1030594-38-7

• 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: (E)-3-[4-(5-bromopentoxy)phenyl]-1-phenylprop-2-en-1-one
• CAS: 1030594-38-7
• 化学式: C₂₀H₂₁BrO₂
• 分子量: 373.29
• InChiKey: FHGFQPAQGAWOMO-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  哌嗪 、 (E)-3-[4-(5-bromopentoxy)phenyl]-1-phenylprop-2-en-1-one 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 (E)-1-phenyl-3-[4-(5-piperazin-1-ylpentoxy)phenyl]prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, physicochemical properties and antimicrobial evaluation of new (E)-chalcones

  摘要：

  In a wide search program towards new and efficient antimicrobial agents, a series of 40 substituted chalcones have been synthesized and tested for their in vitro antibacterial and antifungal activities. The structures of these compounds have been investigated by nuclear magnetic resonance spectroscopy and mass spectrometry. Among the (E)-4-aminoalkylthiochalcones and (E)-4-aminoalkoxychalcones tested, compounds 7, 10, 11, 30 and 31 have exhibited good antibacterial property against Staphylococcus aureus, Enterococcus faecalis and Bacillus subtilis. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.05.006
• 作为产物：
  描述：

  对羟基苯甲醛 在 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 72.0h， 生成 (E)-3-[4-(5-bromopentoxy)phenyl]-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  N‐methylpiperazinyl and piperdinylalkyl‐O‐chalcone derivatives as potential polyfunctional agents against Alzheimer's disease: Design, synthesis and biological evaluation

  摘要：

  摘要 设计、合成了一系列 N-甲基哌嗪基和哌啶基烷基-O-查尔酮衍生物，并利用体外实验对其抑制乙酰胆碱酯酶（AChE）活性、AGEs 和自由基形成的能力进行了生物评估，将其作为抗老年痴呆症的潜在多药。合成的大多数化合物都能抑制乙酰胆碱酯酶的活性；在纳摩尔浓度下，AGEs 还具有清除自由基的活性。其中，化合物 5k 具有强效 AChE 抑制活性（IC50 = 11.6 nM），优于参考化合物多奈哌齐（15.68 nM），同时还具有良好的抗 AGEs 和自由基形成作用。通过对接研究发现，它同时与 AChE 的催化活性位点和外周阴离子位点具有双重结合特性，从而证明了它的有效性。此外，5k 对链脲佐菌素（STZ）诱导的大鼠痴呆症的体内评估也表明，它能改善动物的记忆功能（莫里斯水迷宫测试）。此外，5k 还能抑制 STZ 引起的脑 AChE 活性和氧化应激，这进一步加强了体外观察到的效果。然后，利用基于模拟的相互作用协议分析了配体-蛋白质复合物的稳定性。结果表明，这些 N-甲基哌嗪基和哌啶基烷基-O-查尔酮衍生物可被视为潜在的多功能抗阿尔茨海默氏症分子。

  DOI：

  10.1111/cbdd.14318

文献信息

• Synthesis, physicochemical properties and antimicrobial evaluation of new (E)-chalcones
  作者：Z. Nowakowska、B. Kędzia、G. Schroeder

  DOI：10.1016/j.ejmech.2007.05.006

  日期：2008.4

  In a wide search program towards new and efficient antimicrobial agents, a series of 40 substituted chalcones have been synthesized and tested for their in vitro antibacterial and antifungal activities. The structures of these compounds have been investigated by nuclear magnetic resonance spectroscopy and mass spectrometry. Among the (E)-4-aminoalkylthiochalcones and (E)-4-aminoalkoxychalcones tested, compounds 7, 10, 11, 30 and 31 have exhibited good antibacterial property against Staphylococcus aureus, Enterococcus faecalis and Bacillus subtilis. (c) 2007 Elsevier Masson SAS. All rights reserved.
• <i>N</i>‐methylpiperazinyl and <scp>piperdinylalkyl‐</scp><i>O</i>‐chalcone derivatives as potential polyfunctional agents against Alzheimer's disease: Design, synthesis and biological evaluation
  作者：Pratibha Sharma、Varinder Singh、Manjinder Singh

  DOI：10.1111/cbdd.14318

  日期：2023.11

  The series of N‐methylpiperazinyl and piperdinylalkyl‐O‐chalcone derivatives as potential polyfuctional agents against Alzheimer's disease that have been designed, synthesized and then evaluated biologically using in vitro assays for the inhibition of acetylcholinesterase (AChE) activity, AGEs, and free radical formation. The majority of synthesized compounds inhibited AChE & AGEs with additional free radical scavenging activities at nanomolar concentrations. Among these, compound 5k was found to have potent AChE inhibitory activity (IC₅₀ = 11.6 nM), superior than the reference compound donepezil (15.68 nM) along with the good anti‐AGEs and free radical formation effect. Its potency was justified by docking studies that revealed its dual binding characteristic with both catalytic active site and peripheral anionic site of AChE, simultaneously. Furthermore, the in vivo evaluation of 5k against streptozotocin (STZ)‐induced dementia in rats also showed improvement of memory functions (Morris water maze test) in animals. Also, 5k inhibited STZ‐inudced brain AChE activity and oxidative stress which further strengthen the observed in vitro effects. The stability of the ligand‐protein complex was then analyzed using a simulation‐based interaction protocol. The results revealed that these N‐methylpiperazinyl and piperdinylalkyl‐O‐chalcone derivatives could be considered for potential polyfunctional anti‐Alzheimer's molecules.

  摘要 设计、合成了一系列 N-甲基哌嗪基和哌啶基烷基-O-查尔酮衍生物，并利用体外实验对其抑制乙酰胆碱酯酶（AChE）活性、AGEs 和自由基形成的能力进行了生物评估，将其作为抗老年痴呆症的潜在多药。合成的大多数化合物都能抑制乙酰胆碱酯酶的活性；在纳摩尔浓度下，AGEs 还具有清除自由基的活性。其中，化合物 5k 具有强效 AChE 抑制活性（IC50 = 11.6 nM），优于参考化合物多奈哌齐（15.68 nM），同时还具有良好的抗 AGEs 和自由基形成作用。通过对接研究发现，它同时与 AChE 的催化活性位点和外周阴离子位点具有双重结合特性，从而证明了它的有效性。此外，5k 对链脲佐菌素（STZ）诱导的大鼠痴呆症的体内评估也表明，它能改善动物的记忆功能（莫里斯水迷宫测试）。此外，5k 还能抑制 STZ 引起的脑 AChE 活性和氧化应激，这进一步加强了体外观察到的效果。然后，利用基于模拟的相互作用协议分析了配体-蛋白质复合物的稳定性。结果表明，这些 N-甲基哌嗪基和哌啶基烷基-O-查尔酮衍生物可被视为潜在的多功能抗阿尔茨海默氏症分子。