2-(4-甲氧基苯基)-5-硝基吡啶 | 131941-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-(4-甲氧基苯基)-5-硝基吡啶
• 英文名称: 2-(4-methoxyphenyl)-5-nitropyridine
• CAS: 131941-25-8
• 化学式: C₁₂H₁₀N₂O₃
• 分子量: 230.223
• InChiKey: AQFGZIXPQOUSHT-UHFFFAOYSA-N

物化性质

• 熔点：
  132-135
• 沸点：
  379.7±32.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-(4-甲氧基苯基)-5-硝基吡啶 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 6-(4-甲氧基苯基)吡啶-3-胺
  参考文献：
  名称：

  Activity of 2,6,9-trisubstituted purines as potent PDGFRα kinase inhibitors with antileukaemic activity

  摘要：

  Receptor tyrosine kinase PDGFR alpha is often constitutively activated in various tumours and is regarded as a drug target. Here, we present a collection of 2,6,9-trisubstituted purines with nanomolar potency against PDGFR alpha and strong and selective cytotoxicity in the human eosinophilic leukaemia cell line EOL-1 that expresses the FIP1L1-PDGFRA oncogene. In treated EOL-1 cells, the example compound 14q inhibited the autophosphorylation of PDGFR alpha and the phosphorylation of STAT3 and ERK1/2. Interestingly, we observed pronounced and even increased effects of 14q on PDGFR alpha and some of its downstream signalling pathways after drug washout. In accordance with suppressed PDGFR alpha signalling, treated cells were arrested in the G1 phase of the cell cycle and eventually underwent apoptosis. Our results show that substituted purines can be used as specific modulators of eosinophilic leukaemia. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111663
• 作为产物：
  描述：

  2-溴-5-硝基吡啶 、 4-甲氧基苯硼酸 在 potassium phosphate monohydrate 、 四丁基溴化铵 、 palladium diacetate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-(4-甲氧基苯基)-5-硝基吡啶
  参考文献：
  名称：

  Activity of 2,6,9-trisubstituted purines as potent PDGFRα kinase inhibitors with antileukaemic activity

  摘要：

  Receptor tyrosine kinase PDGFR alpha is often constitutively activated in various tumours and is regarded as a drug target. Here, we present a collection of 2,6,9-trisubstituted purines with nanomolar potency against PDGFR alpha and strong and selective cytotoxicity in the human eosinophilic leukaemia cell line EOL-1 that expresses the FIP1L1-PDGFRA oncogene. In treated EOL-1 cells, the example compound 14q inhibited the autophosphorylation of PDGFR alpha and the phosphorylation of STAT3 and ERK1/2. Interestingly, we observed pronounced and even increased effects of 14q on PDGFR alpha and some of its downstream signalling pathways after drug washout. In accordance with suppressed PDGFR alpha signalling, treated cells were arrested in the G1 phase of the cell cycle and eventually underwent apoptosis. Our results show that substituted purines can be used as specific modulators of eosinophilic leukaemia. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111663

文献信息

• A highly active catalytic system for Suzuki–Miyaura cross-coupling reactions of aryl and heteroaryl chlorides in water
  作者：Shu-Lan Mao、Yue Sun、Guang-Ao Yu、Cui Zhao、Zhi-Jun Han、Jia Yuan、Xiaolei Zhu、Qihua Yang、Sheng-Hua Liu

  DOI：10.1039/c2ob26463c

  日期：——

  An easily available Pd(OAc)2/(2-mesitylindenyl)dicyclohexylphosphine/Me(octyl)3N+Cl−/K3PO4·3H2O catalytic system was developed and it shows high catalytic activity in the Suzuki–Miyaura cross-coupling reaction of a diverse array of aryl and heteroaryl chlorides in water. Notably, this catalytic system also works with ultra-low loading of the catalyst with high turnover numbers.

  容易获得的Pd（OAc）2 /（2-异丁烯基）二环己基膦/ Me的（辛基）3 Ñ +氯- / K 3 PO 4 ·3H 2 ö催化体系被开发，它示出了在芳基和杂芳基氯化物的多样性阵列的Suzuki-Miyaura交叉偶联反应的高催化活性水。值得注意的是，该催化系统还可以在超低负荷下以高周转数运行。
• Nucleophilic Reaction upon Electron-Deficient Pyridone Derivatives. X.One-Pot Synthesis of 3-Nitropyridines by Ring Transformation of 1-Methyl-3,5-dinitro-2-pyridone with Ketones or Aldehydes in the Presence of Ammonia
  作者：Yasuo Tohda、Miyuki Eiraku、Takao Nakagawa、Yumi Usami、Masahiro Ariga、Toshihide Kawashima、Keita Tani、Hiroko Watanabe、Yutaka Mori

  DOI：10.1246/bcsj.63.2820

  日期：1990.10

  The reaction of 1-methyl-3,5-dinitro-2-pyridone (1a) with ketones or aldehydes in the presence of ammonia gave alkyl- and/or aryl-substituted 3-nitropyridines (6) in moderate to high yields. Enamines derived from the ketones gave better results than did the ketones themselves; on the other hand, those derived from the aldehydes gave no 6 at all. On the basis of deuterium-labeled experiments, a mechanism comprising competitive ring transformations of 1a is proposed.

  在氨存在下，1-甲基-3,5-二硝基-2-吡啶酮（1a）与酮或醛反应，以中等至高产率得到烷基和/或芳基取代的3-硝基吡啶（6）。由酮衍生的烯胺比酮本身得到的结果更好；另一方面，由醛衍生的烯胺完全没有得到6。基于氘标记实验，提出了一个涉及1a竞争性环转换的机理。
• An active catalytic system for Suzuki–Miyaura cross-coupling reactions using low levels of palladium loading
  作者：Meng-Qi Yan、Jia Yuan、Fang Lan、Si-Hao Zeng、Meng-Yue Gao、Sheng-Hua Liu、Jian Chen、Guang-Ao Yu

  DOI：10.1039/c7ob00178a

  日期：——

  An easily available Pd(OAc)2/(2-(anthracen-9-yl)-1H-inden-3-yl) dicyclohexylphosphine/toluene/iPrOH/water catalytic system was developed, which shows high catalytic activity in the Suzuki–Miyaura cross-coupling reactions of a diverse array of aryl and heteroaryl chlorides with Pd loadings down to 0.01 mol%.

  容易获得的Pd（OAC）2 /（2-（蒽-9-基）-1- ħ茚-3-基）二环己基膦/甲苯/我异丙醇/水催化体系被开发，其显示高的催化在铃木活动–Miyaura的各种芳基和杂芳基氯化物的交叉偶联反应，其Pd含量低至0.01 mol％。
• Palladium(II) Catalyzed Suzuki/Sonogashira Cross-Coupling Reactions of Sulfonates: An Efficient Approach to C2-Functionalized Pyrimidines and Pyridines
  作者：Zheng-Jun Quan、Fu-Qiang Jing、Zhang Zhang、Yu-Xia Da、Xi-Cun Wang

  DOI：10.1002/ejoc.201300592

  日期：2013.11

  Pyrimidin-2-yl sulfonates, as a reaction partner, can be easily prepared from inexpensive commercial materials and are efficiently cross-coupled with arylboronic acids and terminal alkynes by using Pd(OAc)2-catalyzed Suzuki and Sonogashira reactions. A wide array of C2-functionalized pyrimidines have been prepared in good to excellent yields. 2-Arylpyridines and 2-(oct-1-ynyl)pyridine were also synthesized

  嘧啶-2-基磺酸盐作为反应伙伴，可以从廉价的商业材料中轻松制备，并通过使用 Pd(OAc)2 催化的 Suzuki 和 Sonogashira 反应与芳基硼酸和末端炔烃有效交叉偶联。大量 C2 官能化的嘧啶已经以良好到极好的产率制备。还合成了 2-芳基吡啶和 2-(oct-1-ynyl) 吡啶。
• Agent for Treatment of Eye Diseases
  申请人：Kakizuka Akira

  公开号：US20140148416A1

  公开（公告）日：2014-05-29

  The present invention provides agents effective to treat eye diseases, pharmaceutical compositions comprising them, methods for preparing pharmaceuticals for treatment of eye diseases comprising using the agents, use of the agents in manufacture of pharmaceuticals for treatment of eye diseases and methods for treating eye diseases comprising administering the agents or the pharmaceutical compositions. The eye diseases treated by the present invention include particularly glaucoma, especially normal tension glaucoma, or retinitis pigmentosa. The present invention provides the compound of formula (I) wherein R is as defined in the description.

  本发明提供了治疗眼部疾病的有效药剂，包括它们的制药组合物，制备用于治疗眼部疾病的药物的方法，包括使用这些药剂，以及在制造用于治疗眼部疾病的药物时使用这些药剂的方法，以及通过给药这些药剂或药物组合物来治疗眼部疾病的方法。本发明治疗的眼部疾病包括青光眼，特别是正常张力青光眼，或色素性视网膜病变。本发明提供了式（I）的化合物，其中R在说明中定义。