(2E)-3-(4-bromophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one

• 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: (2E)-3-(4-bromophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-3-(4-bromophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₅BrO₃
• 分子量: 347.208
• InChiKey: AQCGUPISNITRRV-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-3-(4-bromophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one 在 三氟乙酸 作用下， 反应 0.33h， 以52%的产率得到3-(4-Bromo-phenyl)-5,6-dimethoxy-indan-1-one
  参考文献：
  名称：

  The synthesis of indanones related to combretastatin A-4 via microwave-assisted Nazarov cyclization of chalcones

  摘要：

  A fast and efficient microwave-assisted synthesis of combretastatin A-4-like indationes has been developed. Microwave irradiation provides a useful alternative to traditional heating techniques to promote the TFA-catalyzed Nazarov cyclization of chalcones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.110
• 作为产物：
  描述：

  (2E)-1-(3,4-dimethoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one 在 sodium hydroxide 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 (2E)-3-(4-bromophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  The synthesis of indanones related to combretastatin A-4 via microwave-assisted Nazarov cyclization of chalcones

  摘要：

  A fast and efficient microwave-assisted synthesis of combretastatin A-4-like indationes has been developed. Microwave irradiation provides a useful alternative to traditional heating techniques to promote the TFA-catalyzed Nazarov cyclization of chalcones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.110

文献信息

• A novel series of benzothiazepine derivatives as tubulin polymerization inhibitors with anti-tumor potency
  作者：Bin Wang、Li-Ren Wang、Lu-Lu Liu、Wei Wang、Ruo-Jun Man、Da-Jun Zheng、Yu-Shan Deng、Yu-Shun Yang、Chen Xu、Hai-Liang Zhu

  DOI：10.1016/j.bioorg.2020.104585

  日期：2021.3

  In this work, a series of diaryl benzo[b][1,4]thiazepine derivatives D1-D36 were synthesized and screened as tubulin polymerization inhibitors with anti-tumor potency. They were designed by introducing the seven-member ring benzothiazepine as the linker for CA-4 modification for the first time. Among them, the hit compound D8 showed potential on inhibiting the growth of several cancer cell lines (IC50

  在这项工作中，合成并筛选了一系列二芳基苯并[ b ] [1,4] 硫氮杂衍生物D1-D36作为具有抗肿瘤效力的微管蛋白聚合抑制剂。它们是通过首次引入七元环苯并噻嗪作为 CA-4 修饰的接头而设计的。其中，命中化合物D8显示出抑制多种癌细胞系生长的潜力（IC 50值：HeLa 1.48 μM，MCF-7 1.47 μM，HT29 1.52 μM 和 A549 1.94 μM），与阳性对照秋水仙碱和CA-4P。D8的计算 IC 50值作为微管蛋白聚合抑制剂的浓度为 1.20 μM。流式细胞术检测结果表明，D8可以诱导有丝分裂灾难和活癌细胞的死亡。D8还表明了抗血管活性。对接模拟暗示了可能的结合模式，推断引入与附近微管蛋白链相互作用的可能性。由于新的结构试验已经进行了初步讨论，这项工作可能会激发进一步修改微管蛋白相关抗癌药物和治疗方法的新思路。
• Effect on Acetylcholinesterase and Anti-oxidant Activity of Synthetic Chalcones having a Good Predicted Pharmacokinetic Profile
  作者：Renata P. Sakata、Micheli Figueiro、Daniel F. Kawano、Wanda P. Almeida

  DOI：10.2174/1573406413666170525125730

  日期：2017.10.17

  Background: Acetylcholinesterase (AChE) is an important target in the development of drug to treat Alzheimer's disease (AD). In this work, we investigated the effect of twenty-two synthesized chalcones on AChE activity. Objective: This work is aimed to synthesize and evaluate the effect of chalcones on the AChE activity, as well as anti-oxidant activity and predict their pharmacokinetic profile. Method: Chalcones were synthesized through a Claisen-Schmidt condensation and their inhibitory effect on the AChE was evaluated by the Elmann's colorimetric method. To determine the anti-oxidant activity the DPPH radical scavenging method was chosen. Results: We found that all chalcones inhibit this activity, with IC50 values ranging from 0.008 to 4.8 µM. We selected the most active compound 19 with an IC50 value of 0.008 µM for a kinetic study demonstrating a competitive inhibition mode. Molecular docking simulations showed a good interaction between 19 and the active site of AChE. Considering the prediction of pharmacokinetic parameters being a useful tool for selecting potential drug candidates, our study results suggest that the majority of chalcones, including the most active one, have a promising pharmacokinetic profile and blood-brain barrier permeability. The involvement of reactive oxygen species (ROS) in AD-related events has encouraged us to evaluate these chalcones as radical scavengers. Conclusion: We have found that compound 19 is a potent AChE inhibitor, and based on kinetic studies, it acts as a competitive inhibitor.

  背景：乙酰胆碱酯酶（AChE）是开发治疗阿尔茨海默病（AD）药物的重要靶点。本研究中，我们探讨了22种合成的查尔酮对AChE活性的影响。 目标：本工作的目的是合成并评估查尔酮对AChE活性的影响，以及其抗氧化活性并预测其药代动力学特征。 方法：通过克莱森-施密特缩合合成查尔酮，并采用Elmann比色法评估其对AChE的抑制作用。为了确定抗氧化活性，选择了DPPH自由基清除法。 结果：我们发现所有查尔酮均抑制该活性，IC50值范围为0.008至4.8 µM。我们选择了活性最强的化合物19，其IC50值为0.008 µM，进行动力学研究，结果表明其呈现竞争性抑制模式。分子对接模拟显示化合物19与AChE的活性位点之间有良好的相互作用。考虑到药代动力学参数的预测是选择潜在药物候选物的有用工具，我们的研究结果表明，大多数查尔酮，包括活性最强的，具有良好的药代动力学特征和血脑屏障渗透性。反应性氧种（ROS）在AD相关事件中的参与促使我们评估这些查尔酮作为自由基清除剂的潜力。 结论：我们发现化合物19是一种有效的AChE抑制剂，基于动力学研究，它作为竞争性抑制剂发挥作用。
• The synthesis of indanones related to combretastatin A-4 via microwave-assisted Nazarov cyclization of chalcones
  作者：Nicholas J. Lawrence、E. Simon M. Armitage、Benjamin Greedy、Darren Cook、Sylvie Ducki、Alan T. McGown

  DOI：10.1016/j.tetlet.2005.12.110

  日期：2006.3

  A fast and efficient microwave-assisted synthesis of combretastatin A-4-like indationes has been developed. Microwave irradiation provides a useful alternative to traditional heating techniques to promote the TFA-catalyzed Nazarov cyclization of chalcones. (c) 2006 Elsevier Ltd. All rights reserved.