3-(4-硝基苯氧基)苯甲酸甲酯 | 212189-48-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 3-(4-硝基苯氧基)苯甲酸甲酯
• 英文名称: methyl 3-(4-nitrophenoxy)benzoate
• 英文别名: 3-(4-nitro-phenoxy)-benzoic acid methyl ester；3-(4-Nitro-phenoxy)-benzoesaeure-methylester
• CAS: 212189-48-5
• 化学式: C₁₄H₁₁NO₅
• 分子量: 273.245
• InChiKey: XLZUUZMFAKIMLB-UHFFFAOYSA-N

物化性质

• 沸点：
  396.3±22.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P264,P270,P301+P312,P330
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  3-(4-硝基苯氧基)苯甲酸甲酯 在 铁粉 、 氯化铵 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 34.0h， 生成 3-(4-(3-(4-chlorophenyl)ureido)phenoxy)benzoic acid
  参考文献：
  名称：

  作为潜在 HDAC 抑制剂的新型二芳基醚异羟肟酸衍生物的合成和抗肿瘤活性

  摘要：

  首次合成了一系列二芳基醚异羟肟酸，并对其 HDAC 生物学和抗增殖活性进行了评估。这些新的异羟肟酸衍生物的结构通过IR、1H-NMR和质谱得到证实。这些化合物中的一些在 HDAC 抑制试验中显示出微摩尔活性，并针对四种癌细胞系。

  DOI：

  10.1007/s12272-012-1003-0
• 作为产物：
  描述：

  3-羟基苯甲酸甲酯 、 对氟硝基苯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以85.3%的产率得到3-(4-硝基苯氧基)苯甲酸甲酯
  参考文献：
  名称：

  作为潜在 HDAC 抑制剂的新型二芳基醚异羟肟酸衍生物的合成和抗肿瘤活性

  摘要：

  首次合成了一系列二芳基醚异羟肟酸，并对其 HDAC 生物学和抗增殖活性进行了评估。这些新的异羟肟酸衍生物的结构通过IR、1H-NMR和质谱得到证实。这些化合物中的一些在 HDAC 抑制试验中显示出微摩尔活性，并针对四种癌细胞系。

  DOI：

  10.1007/s12272-012-1003-0

文献信息

• Design and Synthesis of Minimalist Terminal Alkyne-Containing Diazirine Photo-Crosslinkers and Their Incorporation into Kinase Inhibitors for Cell- and Tissue-Based Proteome Profiling
  作者：Zhengqiu Li、Piliang Hao、Lin Li、Chelsea Y. J. Tan、Xiamin Cheng、Grace Y. J. Chen、Siu Kwan Sze、Han-Ming Shen、Shao Q. Yao

  DOI：10.1002/anie.201300683

  日期：2013.8.12

  “clickable” photo‐crosslinker (see scheme) was incorporated with numerous small‐molecule kinase inhibitors. The resulting probes were used for both in vitro (cell lysates) and in situ (live cells) proteome profiling, for large‐scale identification of their potential cellular kinase targets and shows improved outcomes over previous probes.

  少即是多：极简的“可点击”光交联剂（参见方案）与许多小分子激酶抑制剂结合在一起。所得的探针可用于体外（细胞裂解物）和原位（活细胞）蛋白质组分析，以大规模鉴定其潜在的细胞激酶靶标，并显示出比以前的探针更好的结果。
• DIARYLETHER INHIBITORS OF FARNESYL-PROTEIN TRANSFERASE
  作者：Christopher J Dinsmore*、Theresa M Williams、Kelly Hamilton、Timothy J O'Neill、Elaine Rands、Kenneth S Koblan、Nancy E Kohl、Jackson B Gibbs、Samuel L Graham、George D Hartman、Allen I Oliff

  DOI：10.1016/s0960-894x(97)00225-4

  日期：1997.5

  The design and synthesis of simple nonpeptide inhibitors of farnesyl-protein transferase (FTase) are described. Cysteine-derived diarylether frameworks are appropriate structural replacements for the C-terminal tetrapeptide portion of the Ras protein, and possess in vitro potency against FTase. Inhibitory activity is dependent on the ring-substitution pattern, and does not require the presence of a C-terminal carboxylate group. (C) 1997 Elsevier Science Ltd.
• Tomita; Ikawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 1065,1067
  作者：Tomita、Ikawa

  DOI：——

  日期：——
• Novel Deazaflavin Analogues Potently Inhibited Tyrosyl DNA Phosphodiesterase 2 (TDP2) and Strongly Sensitized Cancer Cells toward Treatment with Topoisomerase II (TOP2) Poison Etoposide
  作者：Jayakanth Kankanala、Carlos J. A. Ribeiro、Evgeny Kiselev、Azhar Ravji、Jessica Williams、Jiashu Xie、Hideki Aihara、Yves Pommier、Zhengqiang Wang

  DOI：10.1021/acs.jmedchem.9b00274

  日期：2019.5.9

  Topoisomerase II (TOP2) poisons as anticancer drugs work by trapping TOP2 cleavage complexes (TOP2cc) to generate DNA damage. Repair of such damage by tyrosyl DNA phosphodiesterase 2 (TDP2) could render cancer cells resistant to TOP2 poisons. Inhibiting TDP2, thus, represents an attractive mechanism-based chemosensitization approach. Currently known TDP2 inhibitors lack cellular potency and/or permeability. We report herein two novel subtypes of the deazaflavin TDP2 inhibitor core. By introducing an additional phenyl ring to the N-10 phenyl ring (subtype 11) or to the N-3 site of the deazaflavin scaffold (subtype 12), we have generated novel analogues with considerably improved biochemical potency and/or permeability. Importantly, many analogues of both subtypes, particularly compounds 11a, 11e, 12a, 12b, and 12h, exhibited much stronger cancer cell sensitizing effect than the best previous analogue 4a toward the treatment with etoposide, suggesting that these analogues could serve as effective cellular probes.
• Synthesis and antitumor activity of novel diaryl ether hydroxamic acids derivatives as potential HDAC inhibitors
  作者：Yong Zhu、Xin Chen、Zeng Wu、Yixuan Zheng、Yadong Chen、Weifang Tang、Tao Lu

  DOI：10.1007/s12272-012-1003-0

  日期：2012.10

  A series of diaryl ether hydroxamic acids were synthesized for the first time and evaluated for the HDAC biology and antiproliferative activity. The structures of these new hydroxamic acids derivatives were confirmed by IR, 1H-NMR and mass spectrum. Some of these compounds showed micro molar activity in the HDAC inhibitory assay and against four cancer cell lines.

  首次合成了一系列二芳基醚异羟肟酸，并对其 HDAC 生物学和抗增殖活性进行了评估。这些新的异羟肟酸衍生物的结构通过IR、1H-NMR和质谱得到证实。这些化合物中的一些在 HDAC 抑制试验中显示出微摩尔活性，并针对四种癌细胞系。