2-(2-furanyl)-5-nitropyridine | 131941-30-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-(2-furanyl)-5-nitropyridine
• 英文别名: 2-(Furan-2-yl)-5-nitropyridine；2-(furan-2-yl)-5-nitropyridine
• CAS: 131941-30-5
• 化学式: C₉H₆N₂O₃
• 分子量: 190.158
• InChiKey: IMBKWQHNVCGCSS-UHFFFAOYSA-N

物化性质

• 沸点：
  314.6±27.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-furanyl)-5-nitropyridine 在 铁粉 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.25h， 生成 N-[6-(2-furanyl)pyridin-3-yl]-4-sulfamoylbenzamide
  参考文献：
  名称：

  Structure-Based Ligand Design of Novel Bacterial RNA Polymerase Inhibitors

  摘要：

  Bacterial RNA polymerase (RNAP) is essential for transcription and is an antibacterial target for small molecule inhibitors. The binding region of myxopyronin B (MyxB), a bacterial RNAP inhibitor, offers the possibility of new inhibitor design. The molecular design program SPROUT has been used in conjunction with the X-ray cocrystal structure of Thermus thermophilus RNAP with MyxB to design novel inhibitors based on a substituted pyridyl-benzamide scaffold. A series of molecules, with molecular masses <350 Da, have been prepared using a simple synthetic approach. A number of these compounds inhibited Escherichia coli RNAP.

  DOI：

  10.1021/ml200087m
• 作为产物：
  描述：

  2-羟基-5-硝基吡啶 在 四(三苯基膦)钯 、 sodium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 生成 2-(2-furanyl)-5-nitropyridine
  参考文献：
  名称：

  Structure-Based Ligand Design of Novel Bacterial RNA Polymerase Inhibitors

  摘要：

  Bacterial RNA polymerase (RNAP) is essential for transcription and is an antibacterial target for small molecule inhibitors. The binding region of myxopyronin B (MyxB), a bacterial RNAP inhibitor, offers the possibility of new inhibitor design. The molecular design program SPROUT has been used in conjunction with the X-ray cocrystal structure of Thermus thermophilus RNAP with MyxB to design novel inhibitors based on a substituted pyridyl-benzamide scaffold. A series of molecules, with molecular masses <350 Da, have been prepared using a simple synthetic approach. A number of these compounds inhibited Escherichia coli RNAP.

  DOI：

  10.1021/ml200087m

文献信息

• 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。
• Activity of 2,6,9-trisubstituted purines as potent PDGFRα kinase inhibitors with antileukaemic activity
  作者：Eva Řezníčková、Tomáš Gucký、Veronika Kováčová、Haresh Ajani、Radek Jorda、Vladimír Kryštof

  DOI：10.1016/j.ejmech.2019.111663

  日期：2019.11

  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.