4-(2,4-dinitrophenoxy)benzoic acid | 3761-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2,4-dinitrophenoxy)benzoic acid
• 英文别名: 4-(2,4-Dinitro-phenoxy)-benzoesaeure；2'.4'-Dinitro-diphenylaether-carbonsaeure-(4)
• CAS: 3761-31-7
• 化学式: C₁₃H₈N₂O₇
• 分子量: 304.216
• InChiKey: VIXSKCZNSAEUGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  4-(2,4-dinitrophenoxy)benzoic acid 在 三氯氧磷 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 11.0h， 生成 N-[5-[4-(2,4-dinitrophenoxy)phenyl]-1,3,4-thiadiazol-2-yl]-2-methoxybenzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of novel thiadiazole amides as potent Cdc25B and PTP1B inhibitors

  摘要：

  A series of novel thiadiazole amide derivatives have been synthesized and evaluated for inhibitory activities against Cdc25B and PTP1B. Most of them showed inhibitory activities against Cdc25B (IC50=1.18-8.01 μg/mL) and PTP1B (IC50=0.85-8.75 μg/mL), respectively. Moreover, compounds 5b and 4l were most potent with IC50 values of 1.18 and 0.85 μg/mL for Cdc25B and PTP1B, respectively, compared with reference drugs Na3VO4 (IC50=0.93 μg/mL) and oleanolic acid (IC50=0.85 μg/mL). The results of selectivity experiments showed that the target compounds were selective inhibitors against PTP1B and Cdc25B. Enzyme kinetic experiments demonstrated that compound 5k was a specific inhibitor with the typical characteristics of a mixed inhibitor.

  DOI：

  10.1016/j.bmcl.2014.07.055
• 作为产物：
  描述：

  1-(4-甲基苯氧基)-2,4-二硝基苯 在 potassium dichromate 、 硫酸 作用下， 以 水 为溶剂， 生成 4-(2,4-dinitrophenoxy)benzoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of novel thiadiazole amides as potent Cdc25B and PTP1B inhibitors

  摘要：

  A series of novel thiadiazole amide derivatives have been synthesized and evaluated for inhibitory activities against Cdc25B and PTP1B. Most of them showed inhibitory activities against Cdc25B (IC50=1.18-8.01 μg/mL) and PTP1B (IC50=0.85-8.75 μg/mL), respectively. Moreover, compounds 5b and 4l were most potent with IC50 values of 1.18 and 0.85 μg/mL for Cdc25B and PTP1B, respectively, compared with reference drugs Na3VO4 (IC50=0.93 μg/mL) and oleanolic acid (IC50=0.85 μg/mL). The results of selectivity experiments showed that the target compounds were selective inhibitors against PTP1B and Cdc25B. Enzyme kinetic experiments demonstrated that compound 5k was a specific inhibitor with the typical characteristics of a mixed inhibitor.

  DOI：

  10.1016/j.bmcl.2014.07.055

文献信息

• Chemical validation of a druggable site on Hsp27/HSPB1 using in silico solvent mapping and biophysical methods
  作者：Leah N. Makley、Oleta T. Johnson、Phani Ghanakota、Jennifer N. Rauch、Delaney Osborn、Taia S. Wu、Tomasz Cierpicki、Heather A. Carlson、Jason E. Gestwicki

  DOI：10.1016/j.bmc.2020.115990

  日期：2021.3

  applied mixed solvent molecular dynamics (MixMD) to predict three possible binding sites, which we confirmed using NMR-based solvent mapping. Using this knowledge, we then used NMR spectroscopy to carry out a fragment-based drug discovery (FBDD) screen, ultimately identifying two fragments that bind to one of these sites. A medicinal chemistry effort improved the affinity of one fragment by ~50-fold (16 µM)

  小热休克蛋白 (sHSPs) 的不稳定突变与多种疾病有关；然而，sHSPs 具有构象动态，缺乏酶功能并且没有内源化学配体。这些因素使得小热激蛋白成为典型的“不可成药”靶标，并且使得识别可能结合和稳定它们的分子变得特别具有挑战性。为了探索潜在的解决方案，我们设计了一个多管齐下的筛选工作流程，涉及计算和生物物理配体发现平台的组合。使用 sHSP 家族成员 HSP27/HSPB1 (HSP27c) 的核心结构域作为靶标，我们应用混合溶剂分子动力学 (MixMD) 来预测三个可能的结合位点，并使用基于 NMR 的溶剂图谱证实了这一点。利用这一知识，我们随后使用核磁共振波谱进行基于片段的药物发现 (FBDD) 筛选，最终识别出与这些位点之一结合的两个片段。一项药物化学工作将一个片段的亲和力提高了约 50 倍 (16 µM)，同时保持良好的配体效率（约 0.32 kcal/mol/非氢原子）。最后，我
• Polarization Effects in Aromatic Ethers¹
  作者：Ray Q. Brewster、Robert Slocombe

  DOI：10.1021/ja01220a020

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