ethyl 3-(4-bromophenoxy)propanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 3-(4-bromophenoxy)propanoate
• 英文别名: 3-(4-bromo-phenoxy)-propionic acid ethyl ester；3-(4-Brom-phenoxy)-propionsaeure-aethylester
• 化学式: C₁₁H₁₃BrO₃
• 分子量: 273.126
• InChiKey: AJJDQULZIAKYTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  ethyl 3-(4-bromophenoxy)propanoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以69 %的产率得到3-(4-溴苯氧基)丙酸
  参考文献：
  名称：

  靶向肿瘤微环境的新型MDH抑制剂的设计、合成及生物学评价

  摘要：

  MDH1 和 MDH2 酶在肺癌的存活中起重要作用。本研究合理设计合成了一系列新型肺癌MDH1/2双重抑制剂，并对其SAR进行了仔细研究。在所测试的化合物中，与 LW1497 相比，含有哌啶环的化合物 50 显示出对 A549 和 H460 肺癌细胞系的生长抑制有所改善。化合物50呈剂量依赖性降低A549细胞总ATP含量；它还以剂量依赖性方式显着抑制缺氧诱导因子 1-α (HIF-1α) 的积累和 HIF-1α 靶基因如 GLUT1 和丙酮酸脱氢酶激酶 1 (PDK1) 的表达。此外，化合物 50 在 A549 肺癌细胞缺氧条件下抑制 HIF-1α 调节的 CD73 表达。总的来说，

  DOI：

  10.3390/ph16050683
• 作为产物：
  描述：

  4-溴苯酚 、 3-溴丙酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 ethyl 3-(4-bromophenoxy)propanoate
  参考文献：
  名称：

  The synthesis and evaluation of phenoxyacylhydroxamic acids as potential agents for Helicobacter pylori infections

  摘要：

  Two series of omega-phenoxy contained acylhydroxamic acids as novel urease inhibitors were designed and synthesized. Biological activity evaluations revealed that co-phenoxypropinoylhydroxamic acids were more active than phenoxyacetohydroxamic acids. Out of these compounds, 3-(3,4-dichlorophenoxy)propionylhydroxamic acid c24 showed significant potency against urease in both cell free extract (IC50 = 0.061 +/- 0.003 mu M) and intact cell (IC50 = 0.89 +/- 0.05 mu M), being over 450- and 120-fold more potent than the clinically prescribed urease inhibitor AHA, repectively. Non-linear fitting of experimental data (V-[S]) suggested a mixed-type inhibition mechanism and a dual site binding mode of these compounds.

  DOI：

  10.1016/j.bmc.2018.07.003

文献信息

• CCL5 inhibitors
  申请人：AFECTA PHARMACEUTICALS, INC.

  公开号：US10940132B2

  公开（公告）日：2021-03-09

  Compounds, pharmaceutically acceptable salts, esters, prodrugs, and pharmaceutical compositions thereof are disclosed that are useful for inhibition of the biological activity of CCL5 on mammalian cells, as well as methods of treatment for diseases involving the increased biological activity of CCL5.

  所公开的化合物、药学上可接受的盐、酯、原药及其药物组合物有助于抑制 CCL5 在哺乳动物细胞上的生物活性，以及治疗涉及 CCL5 生物活性增加的疾病的方法。
• 434. Preparation of β-phenoxypropionic acids by the reaction of phenols with ethyl acrylate
  作者：R. H. Hall、E. S. Stern

  DOI：10.1039/jr9490002035

  日期：——
• CCL5 INHIBITORS
  申请人：AFECTA PHARMACEUTICALS, INC.

  公开号：US20200138766A1

  公开（公告）日：2020-05-07

  Compounds, pharmaceutically acceptable salts, esters, prodrugs, and pharmaceutical compositions thereof are disclosed that are useful for inhibition of the biological activity of CCL5 on mammalian cells, as well as methods of treatment for diseases involving the increased biological activity of CCL5.
• CCL5 Inhibitors
  申请人：AFECTA PHARMACEUTICALS, INC.

  公开号：US20210196665A1

  公开（公告）日：2021-07-01

  Compounds, pharmaceutically acceptable salts, esters, prodrugs, and pharmaceutical compositions thereof are disclosed that are useful for inhibition of the biological activity of CCL5 on mammalian cells, as well as methods of treatment for diseases involving the increased biological activity of CCL5.
• The synthesis and evaluation of phenoxyacylhydroxamic acids as potential agents for Helicobacter pylori infections
  作者：Wei-Wei Ni、Qi Liu、Shen-Zhen Ren、Wei-Yi Li、Li-Li Yi、Heng Jing、Li-Xin Sheng、Qin Wan、Ping-Fu Zhong、Hai-Lian Fang、Hui Ouyang、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2018.07.003

  日期：2018.8

  Two series of omega-phenoxy contained acylhydroxamic acids as novel urease inhibitors were designed and synthesized. Biological activity evaluations revealed that co-phenoxypropinoylhydroxamic acids were more active than phenoxyacetohydroxamic acids. Out of these compounds, 3-(3,4-dichlorophenoxy)propionylhydroxamic acid c24 showed significant potency against urease in both cell free extract (IC50 = 0.061 +/- 0.003 mu M) and intact cell (IC50 = 0.89 +/- 0.05 mu M), being over 450- and 120-fold more potent than the clinically prescribed urease inhibitor AHA, repectively. Non-linear fitting of experimental data (V-[S]) suggested a mixed-type inhibition mechanism and a dual site binding mode of these compounds.