(E)-1-(4-(4-bromobutyloxy)phenyl)-3-phenylprop-2-en-1-one | 1262136-39-9

• 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-(4-bromobutyloxy)phenyl)-3-phenylprop-2-en-1-one
• 英文别名: (2E)-1-[4-(4-bromobutoxy)phenyl]-3-phenylprop-2-en-1-one；4'-[(4-bromobutyl)oxy]chalcone；(E)-1-[4-(4-bromobutoxy)phenyl]-3-phenylprop-2-en-1-one
• CAS: 1262136-39-9
• 化学式: C₁₉H₁₉BrO₂
• 分子量: 359.263
• InChiKey: OAFDWJPQCCSBPU-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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-(4-bromobutyloxy)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61.9%的产率得到(E)-1-(4-(4-(dibutylamino)butoxy)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 、 乙腈 为溶剂， 生成 (E)-1-(4-(4-bromobutyloxy)phenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  含[1,2,4]-三唑-[4,3-a]-吡啶的查尔酮衍生物的设计、合成和生物活性研究

  摘要：

  本研究设计并合成了30种含[1,2,4]-三唑-[4,3-a]-吡啶的查耳酮衍生物。抗菌活性结果表明， N26对Xoo 、 Pcb的EC 50值分别为36.41、38.53 μg/mL，优于噻二唑铜的EC 50值分别为60.62、106.75 μg/mL。通过SEM验证了N26对Xoo的细菌抑制活性。初步探讨了N26与Xoo的抗菌机制，实验结果表明，当药物浓度为100 mg/L时， N26对Xoo具有良好的细胞膜通透性，可抑制EPS含量和胞外酶含量的产生，从而破坏Xoo的细胞膜通透性。 Xoo生物膜的完整性达到抑制Xoo的效果。 N26在200mg/L时对马铃薯采后体内病斑具有保护和抑制作用。采用半叶干斑法测定N1 - N30抗TMV活性。 N22的治疗活性和保护活性的EC 50值分别为77.64和81.55 μg/mL，优于NNM（分别为294.27、175.88 μg/mL）。 MST

  DOI：

  10.1016/j.fitote.2023.105739

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。
• Syntheses and Reactions of 4′-[(<i>ω</i>-Bromoalkyl)oxy]-and 4′,4′′′-(Polymethylenedoxy)-bis Substituted Chalcones
  作者：R. S. Sodani、Prakash C. Choudhary、Hari Om Sharma、B. L. Verma

  DOI：10.1155/2010/807059

  日期：——

  Base catalyzed condensation of 4-hydroxyacetophenone (1) with several aldehydes resulted 4′-hydroxychalcones (2a-c). Reaction ofα,ω-dibromoalkanes (3, n=2, 4 & 6) with (2a-c) in equimolar ratio resulted a mixture of 4′-[(ω-bromoalkyl)oxy]- substituted chalcones (4a-i) and 4′,4′′′-(polymethylenedioxy)-bis substituted chalcones (5a-i) separated by ethanol as soluble (4a-i) and insoluble (5a-i) products. Compounds (5a-i) were also synthesized by another route. Compound 1 on treatment with 3 in molar ratio 2:1 resulted 4′,4′′′-(polymethylenedioxy)-diacetophenone (4^#a-c) which on base catalyzed condensation gave compounds (5a-i). Reaction of 4d with substituted phenols and thiophenols gave corresponding phenoxy and thiophenoxy substituted chalcones (6a-f) where as compounds5a, 5b, 5d, 5h and 5eon treatment with hydrazine hydrate furnished corresponding bis-2-pyrazolines (7a-e). The structures of all synthesized compounds were confirmed on the basis of analytical and spectral data.

  4-羟基乙酰苯酮（1）与几种醛基催化的缩合反应产生了4'-羟基查尔酮（2a-c）。α,ω-二溴烷（3，n=2, 4和6）与（2a-c）在等摩尔比下反应产生了一种混合物，包括4'-[(ω-溴烷基)氧基]-取代查尔酮（4a-i）和4',4'''-(聚亚甲基二氧基)-双取代查尔酮（5a-i），通过乙醇分离为可溶性（4a-i）和不溶性（5a-i）产物。化合物（5a-i）也通过另一途径合成。化合物1与3以2:1的物质比反应生成4',4'''-(聚亚甲基二氧基)-二乙酰苯酮（4#a-c），在碱催化缩合反应中生成化合物（5a-i）。4d与取代苯酚和硫酚反应生成相应的苯氧基和硫酚氧基取代的查尔酮（6a-f），而化合物5a、5b、5d、5h和5e在与水合肼处理后产生相应的双-2-吡唑烯（7a-e）。所有合成化合物的结构均基于分析和光谱数据进行确认。
• 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。
• 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