4-(4-苯基苯氧基)丁酸乙酯 | 106970-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(4-苯基苯氧基)丁酸乙酯
• 英文名称: ethyl 4-(4-phenylphenoxy)butanoate
• 英文别名: 4-(4-phenylphenoxy)butanoic acid ethyl ester；Ethyl 4-[([1,1'-biphenyl]-4-yl)oxy]butanoate
• CAS: 106970-47-2
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: NXRXDCVIMHTMCX-UHFFFAOYSA-N

物化性质

• 沸点：
  429.4±38.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  4-(4-苯基苯氧基)丁酸乙酯 在 硫酸 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 6.0h， 生成 (4-(1,1'-biphenyl-4-yloxy)butoxy)acetaldehyde
  参考文献：
  名称：

  Trifluoromethyl ketones as inhibitors of histone deacetylase

  摘要：

  Trifluoromethyl ketones were found to be inhibitors of histone deacetylases (HDACs). Optimization of this series led to the identification of submicromolar inhibitors Such as 20 that demonstrated antiproliferative effects against the HT1080 and MDA 435 cell lines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00754-0
• 作为产物：
  描述：

  3-(4-phenylphenoxy)propionic acid 在 N-甲基吗啉 、 氯化亚砜 、 盐酸羟胺 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 4-(4-苯基苯氧基)丁酸乙酯
  参考文献：
  名称：

  Discovery of Potent Nonpeptide Inhibitors of Stromelysin Using SAR by NMR

  摘要：

  With the use of an NMR-based method, potent (IC50 < 25 nM) nonpeptide inhibitors of the matrix metalloproteinase stromelysin (MMP-3) were discovered. The method, called SAR by NMR (for structure-activity relationships by nuclear magnetic resonance), involves the identification, optimization, and linking of compounds that bind to proximal sites on a protein. Using this technique, two ligands that bind weakly to stromelysin (acetohydroxamic acid, K-D = 17 mM; 3-(cyanomethyl)-4'-hydroxybiphenyl, K-D = 0.02 mM) were identified. On the basis of NMR-derived structural information, the two fragments were connected to produce a 15 nM inhibitor of this enzyme. This compound was rapidly discovered (less than 6 months) and required only a minimal amount of chemical synthesis. These studies indicate that the SAR by NMR method can be effectively applied to enzymes to yield potent lead inhibitors-an important part of the drug discovery process.

  DOI：

  10.1021/ja9702778

文献信息

• Inhibitors of histone deacetylase
  申请人：——

  公开号：US20020177594A1

  公开（公告）日：2002-11-28

  Compounds having the formula 1 or therapeutically acceptable salts thereof, are histone deacetylase (HDAC) inhibitors. Preparation of the compounds, compositions containing the compounds, and treatment of diseases using the compounds are disclosed.

  具有以下化学式的化合物或其治疗上可接受的盐是组蛋白去乙酰化酶（HDAC）抑制剂。本文揭示了该化合物的制备、含有该化合物的组合物以及使用该化合物治疗疾病的方法。
• Synthesis and Spectroscopic Characterization of Chiral Biphenyl-Cholesterol Gels
  作者：H. Cristina Geiger、Melissa Lamson、Daniel J. Galka

  DOI：10.1021/la503954b

  日期：2014.11.25

  gelators was investigated by circular dichroism (CD), absorption, and fluorescence spectroscopies. The gels obtained from BO4-chol and BO8-chol exhibit biphasic circular dichroism spectra with opposite chirality. The ICD spectra of both BO8-chol and BBO8-chol gels show a positive ICD band followed by a negative band at room temperature. However, while BO8-chol gel ICD absorptions decrease equally as temperature

  4-（3-胆固醇氧基羰基丙基氧基）联苯（BO4-chol），4-（7胆固醇氧基羰基庚氧基）联苯（BO8-chol）和4,4'-双（7-胆固醇氧基羰基庚氧基）联苯（BBO8-chol）的合成被报道。这些胶凝剂在正辛醇中形成1％和2％（w / w）的稳定凝胶。由单一胆固醇胶凝剂（BO4-chol和BO8-chol）形成的凝胶的相变温度（T g）（62-65、68-69°C）比从双胆固醇胶凝剂BBO8-chol（96-65）获得的相变温度低（T g）。 98°C）。所有三种胶凝剂在n中形成手性凝胶-辛醇，通过诱导圆二色性（ICD）光谱观察。通过圆二色性（CD），吸收和荧光光谱研究了两个胆固醇部分相对于一个胆固醇单元通过挠性链与联苯分子连接的胆固醇单元的影响，以及链长对这三种新型胶凝剂胶凝能力的影响。 。由BO4-胆甾醇和BO8-胆甾醇获得的凝胶显示出具有相反手性的双相圆二色性光谱。BO8-cho
• Regioselective Alkoxycarbonylation of Allyl Phenyl Ethers Catalyzed by Pd/dppb Under Syngas Conditions
  作者：Manuel Amézquita-Valencia、Howard Alper

  DOI：10.1021/acs.joc.6b00522

  日期：2016.5.6

  A simple and regioselective synthesis of phenoxy esters and phenylthio esters is reported. The products are obtained by selective alkoxycarbonylation catalyzed by Pd2(dba)3, 1,4-bis(diphenylphisphino)butane (dppb), and syngas (CO/H2) in chloroform/alcohol. This methodology affords bifunctional products in good yield with excellent n-selectivity and without the need to use additives.

  报道了苯氧基酯和苯硫基酯的简单且区域选择性的合成。该产品由通过Pd催化的选择性烷氧基羰基而获得2（DBA）3，1,4-双（diphenylphisphino）丁烷（DPPB）的合成气（CO / H，和2）的氯仿/醇。这种方法可提供双收率好的产品，并具有出色的n选择性，并且无需使用添加剂。
• Biphenyl hydroxamate inhibitors of matrix metalloproteinases
  申请人：Abbott Laboratories

  公开号：US05665777A1

  公开（公告）日：1997-09-09

  Compounds of formula ##STR1## or a pharmaceutically acceptable salt thereof inhibit matrix metalloproteinases and TNF.alpha. secretion and are useful in the treatment of inflammatory disease states. Also disclosed are matrix metalloproteinases and TNF.alpha. secretion inhibiting compositions and a method for inhibiting matrix metalloproteinases and TNF.alpha. secretion.

  式##STR1##的化合物或其药用可接受的盐抑制基质金属蛋白酶和TNF.alpha.分泌，并且在治疗炎症性疾病状态中是有用的。还公开了抑制基质金属蛋白酶和TNF.alpha.分泌的组合物和抑制基质金属蛋白酶和TNF.alpha.分泌的方法。
• 10.3390/molecules29102211
  作者：Yan, Xinlin、Hou, Shi、Xing, Cheng、Zhang, Yuanyuan、Chang, Jiajia、Xiao, Junhai、Lin, Feng

  DOI：10.3390/molecules29102211

  日期：——

  Pseudomonas aeruginosa PAO1 to most clinically relevant antimicrobials, the use of traditional antibiotic treatments in hospitals is challenging. The formation of biofilms, which is regulated by the quorum-sensing (QS) system of Pseudomonas aeruginosa (PA), is an important cause of drug resistance. There are three main QS systems in P. aeruginosa: the las system, the rhl system, and the pqs system. The inhibitors

  由于革兰氏阴性菌铜绿假单胞菌 PAO1 对大多数临床相关抗菌药物具有耐药性，因此在医院使用传统抗生素治疗具有挑战性。生物膜的形成受铜绿假单胞菌（PA）群体感应（QS）系统的调节，是产生耐药性的重要原因。铜绿假单胞菌存在三个主要的QS系统：las系统、rhl系统和pqs系统。 las系统的抑制剂是研究最多的。此前筛选时发现化合物AOZ-1对las系统有一定的抑制作用。本研究通过修饰AOZ-1的接头和环，设计并合成了24种化合物。本研究以 C. violaceum CV026 作为报告菌株，首先评估了新化合物对 QS 的抑制作用，并研究了其 SAR。然后，基于化合物AOZ-1衍生物的SAR分析，替换AOZ-1的母核，探索其结构多样性。然后，以3-氨基-四氢-1,3-恶嗪-2-酮为核心，设计并合成了9个新化合物。发现化合物 Y-31 (IC50 = 91.55 ± 3.35 µM) 可抑制 C.