2-(2-氟-4-硝基苯氧基)乙酸 | 399-45-1

• 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: 2-(2-氟-4-硝基苯氧基)乙酸
• 英文名称: 2-(2-fluoro-4-nitrophenoxy)acetic acid
• 英文别名: (2-fluoro-4-nitro-phenoxy)-acetic acid；(2-Fluor-4-nitro-phenoxy)-essigsaeure；(2-Fluoro-4-nitrophenoxy)acetic acid
• CAS: 399-45-1
• 化学式: C₈H₆FNO₅
• 分子量: 215.138
• InChiKey: GTFPUPQBBURCHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-氟-4-硝基苯氧基)乙酸 在 sodium cyanoborohydride 作用下， 生成
  参考文献：
  名称：

  Photoaffinity labeling of the electroplax sodium channel with tetrodotoxin derivatives. II. Comparison of the photoreactivity of different photoactivable groups in the tetrodotoxin binding site.

  摘要：

  我们合成了四种光活化河豚毒素（TTX）衍生物和相应的三价化合物，并对其进行了孔化。引入的光活性基团是硝基叠氮苯基（NAP）基团和三氟甲基重氮基苯甲酰基（TDB）基团，分别作为腈和碳烯的前体，以及氟硝基苯氧基基团的两种异构体，这是一种对亲核物具有选择性的新光活性基团。这四种衍生物与钠通道的结合亲和力与 TTX 相似，但特定光诱导结合值却出乎意料地低（低至 2.5%），这表明光活性基团的方向可能不利于 TTX 结合位点的标记反应。对两种标记的钠通道蛋白进行了纯化和消化。用 TTXenNAP 标记的肽在 0.1% 三氟乙酸-乙腈高效液相色谱法中失去了大部分标记，而用 TTXenTDB 标记的肽在此过程中保留了标记。TTXenTDB标记的肽在反相C4色谱柱上被洗脱成四个主要馏分，回收率为80%。

  DOI：

  10.1248/cpb.38.982
• 作为产物：
  描述：

  (2-氟苯氧基)乙酸 在 硫酸 、 硝酸 作用下， 生成 2-(2-氟-4-硝基苯氧基)乙酸
  参考文献：
  名称：

  Aromatic Fluorine Compounds. VIII. Plant Growth Regulators and Intermediates^1,2

  摘要：

  DOI：

  10.1021/ja01510a021

文献信息

• The anti-invasive role of novel synthesized pyridazine hydrazide appended phenoxy acetic acid against neoplastic development targeting matrix metallo proteases
  作者：Yasser Hussein Eissa Mohammed、Prabhu Thirusangu、Zabiulla、Vigneshwaran V、Prabhakar B.T、Shaukath Ara Khanum

  DOI：10.1016/j.biopha.2017.08.105

  日期：2017.11

  Neoplastic metastasis is a major process where tumor cells migrate from the primary tumor and colonize at other parts of our body to form secondary tumor. Cancer incidences are rising and novel anti-neoplastic compounds with new mechanism of actions are essential for preventing cancer related deaths. In the current examination, a novel series of pyridazine analogues 6a-l was synthesized and evaluated against metastatic neoplastic cells. Experimental data postulated compound 6j has potential cytotoxic efficacy with prolonged activity against various cancer cells, including A549, HepG2, A498, CaSki and SiHa cells. Moreover, compound 6j arrests the A549 migration and invasions markedly by counteracting matrix metalloproteinase (MMP)-2 and MMP-9 expressions. Also, compound 6j proved its potentiality against Dalton's solid lymphoma progression in-vivo by abridging MVD and MMP expressions. Compound 6j interacts with MMP-2 and MMP-9 by H-bond in-silico, thereby down regulates the MMPs action in tumourigenesis. Altogether, we concluded that compound 6j down regulates MMP-2 and MMP-9 and thereby impairs metastatic cancer cell migration and invasions which can be translated into a potent anti-neoplastic agent.
• Aromatic Fluorine Compounds. VIII. Plant Growth Regulators and Intermediates^1,2
  作者：G. C. Finger、M. J. Gortatowski、R. H. Shiley、R. H. White

  DOI：10.1021/ja01510a021

  日期：1959.1
• Photoaffinity labeling of the electroplax sodium channel with tetrodotoxin derivatives. II. Comparison of the photoreactivity of different photoactivable groups in the tetrodotoxin binding site.
  作者：Eiichi YOSHIDA、Hitoshi NAKAYAMA、Yasumaru HATANAKA、Yuichi KANAOKA

  DOI：10.1248/cpb.38.982

  日期：——

  Four photoactivable tetrodotoxin (TTX) derivatives and the corresponding tritiated compounds were synthesized and porified. The photoactivable groups introduced were a nitro-azidophenyl (NAP) group and a trifluoromethyl diazirinobenzoyl (TDB) group, as nitrene and carbene precursors, respectively, as well as two isomers of the fluoronitrophenoxy group, a new photpreactive group selective for nucleophiles. The binding affinities of the four derivatives to the sodium channel were similar to that of TTX, but the values of specific photoincorporation were unexpectedly low (up to 2.5%), suggesting that the photpactivable groups are likely to be oriented unfavorably for labeling reactions in the TTX binding site. Two of the labeled sodium channel proteins were purified and digested. Peptides labeled with TTXenNAP lost most of the label during high performance liquid chromatography in 0.1% trifluoroacetic acid-acetonitrile, while peptides labeled with TTXenTDB retained the labels during the procedures. The TTXenTDB-labeled peptides were eluted in four major fractions with 80% recovery of the amount applied on a reverse-phased C4 column.However, further purification is necessary to identify the labeled sites of the peptides.

  我们合成了四种光活化河豚毒素（TTX）衍生物和相应的三价化合物，并对其进行了孔化。引入的光活性基团是硝基叠氮苯基（NAP）基团和三氟甲基重氮基苯甲酰基（TDB）基团，分别作为腈和碳烯的前体，以及氟硝基苯氧基基团的两种异构体，这是一种对亲核物具有选择性的新光活性基团。这四种衍生物与钠通道的结合亲和力与 TTX 相似，但特定光诱导结合值却出乎意料地低（低至 2.5%），这表明光活性基团的方向可能不利于 TTX 结合位点的标记反应。对两种标记的钠通道蛋白进行了纯化和消化。用 TTXenNAP 标记的肽在 0.1% 三氟乙酸-乙腈高效液相色谱法中失去了大部分标记，而用 TTXenTDB 标记的肽在此过程中保留了标记。TTXenTDB标记的肽在反相C4色谱柱上被洗脱成四个主要馏分，回收率为80%。