4-(2-phosphonoethyl)catechol | 1194473-18-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2-phosphonoethyl)catechol
• 英文别名: 3,4-Dihydroxyphenethylphosphonic Acid；2-(3,4-dihydroxyphenyl)ethylphosphonic acid
• CAS: 1194473-18-1
• 化学式: C₈H₁₁O₅P
• 分子量: 218.146
• InChiKey: HLMBWSDLIBEUBX-UHFFFAOYSA-N

物化性质

• 沸点：
  535.1±60.0 °C(Predicted)
• 密度：
  1.577±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-phosphonoethyl)catechol 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以267 mg的产率得到4-(2-phosphonoethyl)catechol disodium salt
  参考文献：
  名称：

  Coordination Chemistry Based Approach to Lipophilic Inhibitors of 1-Deoxy-d-xylulose-5-phosphate Reductoisomerase

  摘要：

  1-Deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) in the non-mevalonate pathway found in most bacteria is a validated anti-infective drug target. Fosmidomycin, a potent DXR inhibitor, is active against Gram-negative bacteria. A coordination chemistry and structure based approach was used to discover a novel, lipophilic DXR inhibitor with an IC50 of 1.4 mu M. It exhibited a broad spectrum of activity against Gram-negative and -positive bacteria with minimal inhibition concentrations of 20-100 mu M (or 3.7-19 mu g/mL).

  DOI：

  10.1021/jm9012592
• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 在 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 21.17h， 生成 4-(2-phosphonoethyl)catechol
  参考文献：
  名称：

  Substitution of the phosphonic acid and hydroxamic acid functionalities of the DXR inhibitor FR900098: An attempt to improve the activity against Mycobacterium tuberculosis

  摘要：

  Two series of FR900098/fosmidomycin analogs were synthesized and evaluated for MtDXR inhibition and Mycobacterium tuberculosis whole-cell activity. The design rationale of these compounds involved the exchange of either the phosphonic acid or the hydroxamic acid part for alternative acidic and metal-coordinating functionalities. The best inhibitors provided IC(50) values in the micromolar range, with a best value of 41 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.005

文献信息

• NOVEL DXR INHIBITORS FOR ANTIMICROBIAL THERAPY
  申请人：Song Yongcheng

  公开号：US20130065857A1

  公开（公告）日：2013-03-14

  The present invention generally concerns particular methods and compositions for antimicrobial therapy. In particular embodiments, the compositions target DXR. In specific embodiments, the compositions are electron-deficient heterocyclic rings.

  本发明通常涉及特定的抗微生物治疗方法和组合物。在特定实施例中，该组合物针对DXR。在具体实施例中，该组合物是电子不足的杂环环。
• Inhibitory activity of catecholic phosphonic and phosphinic acids against Helicobacter pylori ureolysis
  作者：Marta Maślanka、Wojciech Tabor、Paweł Krzyżek、Agnieszka Grabowiecka、Łukasz Berlicki、Artur Mucha

  DOI：10.1016/j.ejmech.2023.115528

  日期：2023.9

  carboxylate and phosphonic/phosphinic functionalities and assumed expanded specific interactions. When studying the chemical stability of the molecules, we found that their intrinsic acidity catalyzes spontaneous esterification/hydrolysis reactions in methanol or water solutions, respectively. Regarding biological activity, the most promising compound, 2-(3,4-dihydroxyphenyl)-3-phosphonopropionic acid (), exhibited

  据报道，儿茶酚是脲酶的有效共价抑制剂，它们通过修饰酶活性位点入口处的半胱氨酸残基而表现出活性。遵循这些原则，我们设计并合成了包含羧酸盐和膦酸/次膦酸官能团的新型儿茶酚衍生物，并假设扩大了特定的相互作用。在研究分子的化学稳定性时，我们发现它们的固有酸性分别催化甲醇或水溶液中的自发酯化/水解反应。在生物活性方面，最有前途的化合物2-(3,4-二羟基苯基)-3-膦酰基丙酸()表现出显着的抗脲酶潜力（= 2.36 μM，脲酶），这反映在活细胞中的抗尿素分解作用中亚微摩尔浓度 (IC = 0.75 μM)。正如分子模型所示，该化合物通过一组协调的静电和氢键相互作用结合在脲酶的活性位点上。儿茶酚膦酸的抗尿素分解活性可能是特异性的，因为这些化合物具有化学惰性并​​且对真核细胞没有细胞毒性。
• Substitution of the phosphonic acid and hydroxamic acid functionalities of the DXR inhibitor FR900098: An attempt to improve the activity against Mycobacterium tuberculosis
  作者：Mounir Andaloussi、Martin Lindh、Christofer Björkelid、Surisetti Suresh、Anna Wieckowska、Harini Iyer、Anders Karlén、Mats Larhed

  DOI：10.1016/j.bmcl.2011.07.005

  日期：2011.9

  Two series of FR900098/fosmidomycin analogs were synthesized and evaluated for MtDXR inhibition and Mycobacterium tuberculosis whole-cell activity. The design rationale of these compounds involved the exchange of either the phosphonic acid or the hydroxamic acid part for alternative acidic and metal-coordinating functionalities. The best inhibitors provided IC(50) values in the micromolar range, with a best value of 41 mu M. (C) 2011 Elsevier Ltd. All rights reserved.
• Coordination Chemistry Based Approach to Lipophilic Inhibitors of 1-Deoxy-<scp>d</scp>-xylulose-5-phosphate Reductoisomerase
  作者：Lisheng Deng、Sandeep Sundriyal、Valentina Rubio、Zheng-zheng Shi、Yongcheng Song

  DOI：10.1021/jm9012592

  日期：2009.11.12

  1-Deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) in the non-mevalonate pathway found in most bacteria is a validated anti-infective drug target. Fosmidomycin, a potent DXR inhibitor, is active against Gram-negative bacteria. A coordination chemistry and structure based approach was used to discover a novel, lipophilic DXR inhibitor with an IC50 of 1.4 mu M. It exhibited a broad spectrum of activity against Gram-negative and -positive bacteria with minimal inhibition concentrations of 20-100 mu M (or 3.7-19 mu g/mL).