(E)-1-(4-(3-bromopropyloxy)phenyl)-3-phenylprop-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: (E)-1-(4-(3-bromopropyloxy)phenyl)-3-phenylprop-2-en-1-one
• 英文别名: (2E)-1-[4-(3-bromopropoxy)phenyl]-3-phenylprop-2-en-1-one；(E)-1-[4-(3-bromopropoxy)phenyl]-3-phenylprop-2-en-1-one
• 化学式: C₁₈H₁₇BrO₂
• 分子量: 345.236
• InChiKey: JKWBHYOBQKKGFC-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (E)-1-(4-(3-bromopropyloxy)phenyl)-3-phenylprop-2-en-1-one 、 二正丁胺 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以72.5%的产率得到(E)-1-(4-(3-(dibutylamino)propoxy)phenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of chalcone derivatives as acetylcholinesterase inhibitors

  摘要：

  A novel series of chalcone derivatives (4a-8d) were designed, synthesized, and evaluated for the inhibition activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The logP values of the compounds were shown to range from 1.49 to 2.19, which suggested that they were possible to pass blood brain barriers in vivo. The most promising compound 4a (IC50: 4.68 mu mol/L) was 2-fold more potent than Rivastigmine against AChE (IC50: 10.54 mu mol/L) and showed a high selectivity for AChE over BuChE (ratio: 4.35). Enzyme kinetic study suggested that the inhibition mechanism of compound 4a was a mixed-type inhibition. Meanwhile, the result of molecular docking showed its potent inhibition of AChE and high selectivity for AChE over BuChE. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.08.033
• 作为产物：
  描述：

  对羟基苯乙酮 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 生成 (E)-1-(4-(3-bromopropyloxy)phenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  设计，合成和生物评价的偶联的生物活性支架作为潜在的抗癌剂的二氢叶酸还原酶和硫氧还蛋白还原酶的双重目标。

  摘要：

  二氢叶酸还原酶（DHFR）和硫氧还蛋白还原酶（TrxR）酶参与肿瘤细胞的生长和存活过程。众所周知，4,6-二氨基-1,2-二氢-1,3,5-三嗪支架可作为抑制DHFR的有用支架，而据报道查耳酮是TrxR的抑制剂。在这项研究中，成功​​地合成和表征了通过4,6-二氨基-1,2-二氢-1,3,5-三嗪和查尔酮骨架的结构组合设计的15种新化合物。通过体外酶法评估时，所有化合物均显示出对DHFR和TrxR的双重抑制作用。这些化合物还对MCF-7和HCT116细胞显示出抗增殖活性。更强大的类似物14和15被发现抑制HCT116细胞中的细胞DHFR和TrxR活性。因此，这项研究提供了令人信服的证据，表明14和15可以通过在细胞水平上进行多靶点抑制来发挥其抗癌作用。

  DOI：

  10.1021/acs.jmedchem.6b01253

文献信息

• Design, Synthesis, and Biological Evaluation of Coupled Bioactive Scaffolds as Potential Anticancer Agents for Dual Targeting of Dihydrofolate Reductase and Thioredoxin Reductase
  作者：Hui-Li Ng、Xiang Ma、Eng-Hui Chew、Wai-Keung Chui

  DOI：10.1021/acs.jmedchem.6b01253

  日期：2017.3.9

  The dihydrofolate reductase (DHFR) and thioredoxin reductase (TrxR) enzymes are involved in the process of tumor cell growth and survival. The 4,6-diamino-1,2-dihydro-1,3,5-triazine scaffold is well-established as a useful scaffold for DHFR inhibition, while chalcones have been reported to be inhibitors of TrxR. In this study, 15 novel compounds designed by the structural combination of the 4,6-diamino-1

  二氢叶酸还原酶（DHFR）和硫氧还蛋白还原酶（TrxR）酶参与肿瘤细胞的生长和存活过程。众所周知，4,6-二氨基-1,2-二氢-1,3,5-三嗪支架可作为抑制DHFR的有用支架，而据报道查耳酮是TrxR的抑制剂。在这项研究中，成功​​地合成和表征了通过4,6-二氨基-1,2-二氢-1,3,5-三嗪和查尔酮骨架的结构组合设计的15种新化合物。通过体外酶法评估时，所有化合物均显示出对DHFR和TrxR的双重抑制作用。这些化合物还对MCF-7和HCT116细胞显示出抗增殖活性。更强大的类似物14和15被发现抑制HCT116细胞中的细胞DHFR和TrxR活性。因此，这项研究提供了令人信服的证据，表明14和15可以通过在细胞水平上进行多靶点抑制来发挥其抗癌作用。
• Liquid crystal aligning agent,method of forming a liquid crystal alignment film and liquid crystal display element
  申请人：JSR Corporation

  公开号：EP1336636A1

  公开（公告）日：2003-08-20

  A liquid crystal aligning agent which can provide liquid crystal aligning capability through exposure to polarized radiation without rubbing and which is used to form a liquid crystal alignment film, a method of forming a liquid crystal alignment film, and a liquid crystal display element having this liquid crystal alignment film. An alignment film is formed from a liquid crystal aligning agent containing a polymer having a polyamic acid ester structure with a conjugated enone structure in the side chain and applying radiation to it from a predetermined direction. Thereby, a liquid crystal display element having high thermal stability in the alignment of liquid crystals and excellent display characteristics can be manufactured.

  一种液晶配向剂，可通过暴露于偏振辐射而无需摩擦，从而提供液晶配向能力，该液晶配向剂用于形成液晶配向膜；一种液晶配向膜的形成方法；以及一种具有该液晶配向膜的液晶显示元件。 对准膜是由液晶对准剂形成的，该液晶对准剂含有一种聚合物，该聚合物具有聚酰胺酸酯结构，其侧链具有共轭烯酮结构，然后从预定方向对其进行辐射。这样，就能制造出一种液晶排列热稳定性高、显示特性优异的液晶显示元件。
• Antiviral activity evaluation and action mechanism of chalcone derivatives containing phenoxypyridine
  作者：Piao Mao、Li Xing、Bangcan He、Tianyu Deng、Yishan Qin、Yuzhi Hu、Youshan An、Wei Xue

  DOI：10.1007/s11030-024-10843-7

  日期：——

  In this paper, a series of phenoxypyridine-containing chalcone derivatives (L1–L28) were designed and synthesized, characterized on NMR and HRMS. Ningnanmycin (NNM) was used as a control agent. The results of the antiviral activity testing showed that the curative activity EC50 values of L1 and L4 against TMV were 140.5 and 90.7 μg/mL, respectively, which were superior to that of NNM (148.3 μg/mL)

  本文设计并合成了一系列含苯氧基吡啶的查尔酮衍生物( L1 – L28 )，并通过NMR和HRMS进行了表征。宁南霉素（NNM）用作对照剂。抗病毒活性测试结果显示， L1和L4对TMV的疗效EC 50值分别为140.5和90.7 μg/mL，优于NNM（148.3 μg/mL）。 L1 、 L4和L15的抗TMV保护活性的EC 50值分别为154.1、102.6和140.0μg/mL，优于NNM(188.2μg/mL)。初步探讨了L4和NNM与烟草花叶病毒衣壳蛋白(TMV-CP)的作用机制。微尺度热泳（MST）实验结果表明， L4对TMV-CP具有很强的结合亲和力，解离常数Kd值为0.00149 µM，优于NNM（2.73016 µM）。分子对接实验结果表明， L4与TMV-CP的氨基酸残基形成的氢键比NNM更短，形成的氨基酸残基比NNM更多，这表明L4与TMV-CP的结合更紧密。本研究表明
• Liquid crystal aligning agent, method of forming a liquid crystal alignment film and liquid crystal display element
  申请人：JSR CORPORATION

  公开号：US20040009310A1

  公开（公告）日：2004-01-15

  A liquid crystal aligning agent which can provide liquid crystal aligning capability through exposure to polarized radiation without rubbing and which is used to form a liquid crystal alignment film, a method of forming a liquid crystal alignment film, and a liquid crystal display element having this liquid crystal alignment film. An alignment film is formed from a liquid crystal aligning agent containing a polymer having a polyamic acid ester structure with a conjugated enone structure in the side chain and applying radiation to it from a predetermined direction. Thereby, a liquid crystal display element having high thermal stability in the alignment of liquid crystals and excellent display characteristics can be manufactured.
• US6887534B2
  申请人：——

  公开号：US6887534B2

  公开（公告）日：2005-05-03