1-[(4-fluorobenzyl)oxy]-3-nitrobenzene | 79807-98-0

• 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: 1-[(4-fluorobenzyl)oxy]-3-nitrobenzene
• 英文别名: 1-(4-fluorobenzyloxy)-3-nitrobenzene；1-[(4-Fluorophenyl)methoxy]-3-nitrobenzene
• CAS: 79807-98-0
• 化学式: C₁₃H₁₀FNO₃
• 分子量: 247.226
• InChiKey: IKCOZAPCQQWBGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  383.2±22.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(4-fluorobenzyl)oxy]-3-nitrobenzene 在 一水合肼 作用下， 以 甲醇 为溶剂， 生成 3-[(4-氟苄基)氧基]苯胺
  参考文献：
  名称：

  具有抗凝活性的P1处带有4-（Piperidin-1-yl）吡啶的直接凝血酶抑制剂的合成及生物学评价

  摘要：

  描述了一种新型的非肽类直接凝血酶抑制剂的设计和合成，该抑制剂建立在1-（吡啶-4-基）哌啶-4-羧酰胺的结构上。从显示弱的凝血酶（fIIa）和Xa因子（fXa）抑制活性的强碱性1- ami基哌啶衍生物（6）开始，通过优化碱性P1和X-取代的苯基P4可显着提高抗fIIa活性和人工膜通透性结合部分。结构-活性关系研究以及有用的分子建模结果使我们得以鉴定出化合物13b，该化合物表现出出色的fIIa抑制作用（K i = 6 nM），抗Xa活性弱（K i= 5.64μM），并且对其他丝氨酸蛋白酶（例如胰蛋白酶）具有显着的选择性。化合物13b在低微摩尔范围内显示出体外抗凝活性，并具有显着的膜通透性。在小鼠中（离体），13b在口服给药（100 mg·kg –1）后2 h表现出抗凝作用，与对照组相比，活化的部分凝血活酶时间（aPTT）延长了43％（P <0.05）。

  DOI：

  10.1021/jm401169a
• 作为产物：
  描述：

  间硝基苯酚 、 4-氟溴苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 1-[(4-fluorobenzyl)oxy]-3-nitrobenzene
  参考文献：
  名称：

  Fluorinated Benzyloxyphenyl Piperidine-4-carboxamides with Dual Function against Thrombosis: Inhibitors of Factor Xa and Platelet Aggregation

  摘要：

  A series of benzyloxy anilides of nipecotic (5, 6) and isonipecotic (7, 8) acids were synthesized and assayed in vitro as inhibitors of ADP-induced platelet aggregation and the blood coagulation enzymes factor Xa (FXa) and thrombin (FIIa). An exploration of effects of the amidine group attached at the piperidine nitrogen,position and substitution (F, phenyl) of the benzyloxy group, and addition of fluorine/s on the second (distal) phenyl ring, led us to single out some promising isonipecotamide derivatives 7. Addition of meta-F and para-CF3 on the distal phenyl ring resulted in a 6-to-18-fold enhancement of the FXa potency and in 2-to-4-fold increase of the antiplatelet potency, the last depending to a large extent upon lipophilicity. Two congeners of N-{[3-(1,1'-biphenyl-4-yl)methoxy]phenyl}piperidine-4-carboxamide (7m and 7p) proved to be potent FXa-selective inhibitors (K-i = 130 and 57 nM, respectively) and antiplatelet agents and were identified as leads for developing new dual function antithrombotic drugs.

  DOI：

  10.1021/jm801141f

文献信息

• Veeraswamy; Kurumurthy; Santhosh Kumar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 9, p. 1369 - 1375
  作者：Veeraswamy、Kurumurthy、Santhosh Kumar、Sambasiva Rao、Thelakkat, Kavya、Kotamraju, Srigiridhar、Narsaiah

  DOI：——

  日期：——
• 4-Hydroxyquinoline-3-carboxylic acids as inhibitors of cell respiration. 2. Quantitative structure-activity relationship of dehydrogenase enzyme and Ehrlich ascites tumor cell inhibitions
  作者：Eugene A. Coats、Kishorkant J. Shah、Stanley R. Milstein、Clara S. Genther、Dilip M. Nene、Jeffrey Roesener、James Schmidt、Michael Pleiss、Ellen Wagner、John K. Baker

  DOI：10.1021/jm00343a011

  日期：1982.1

  Studies on dehydrogenase enzyme inhibition have been extended with the design, synthesis, and correlation analysis of 7-[(substituted-benzyl)oxy]-, 7-[(substituted-phenethyl)oxy]-, and 7([substituted-phenoxy)ethoxy]-4-hydroxyquinoline-3-carboxylic acids. Sixteen new congeners and the fifteen molecules previously synthesized have been tested against cytoplasmic malate dehydrogenase and lactate dehydrogenase, as well as against mitochondrial malate dehydrogenase. The lipophilic congeners show a clear specificity for inhibition of the mitochondrial enzyme. Correlation analysis of the data on the three enzymes allows a comparison of the binding sites in quantitative terms, while examination of the data on inhibition of ascites tumor cell respiration affords an indication of membrane transport. A newly developed high-pressure liquid chromatography based retention index is compared to the octanol-water pi constant as a model for hydrophobic interactions.