6-(吡啶-2-基)-2,3-二氢吡嗪-3-酮 | 66317-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-(吡啶-2-基)-2,3-二氢吡嗪-3-酮
• 英文名称: 6-Pyridin-2-ylpyridazin-3-ol
• 英文别名: 3-pyridin-2-yl-1H-pyridazin-6-one
• CAS: 66317-38-2
• 化学式: C₉H₇N₃O
• 分子量: 173.174
• InChiKey: DDCLFSUBVBCSFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(吡啶-2-基)-2,3-二氢吡嗪-3-酮 在 三氯氧磷 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 18.0h， 以100%的产率得到3-氯-6-(2-吡啶基甲基)哒嗪
  参考文献：
  名称：

  LINEAR PYRIDAZINE AND PYRROLE COMPOUNDS, METHOD FOR OBTAINING THEM AND APPLICATIONS

  摘要：

  本发明涉及线性吡啶二氮杂环化合物，更特别涉及这些化合物中的寡吡啶二氮杂环化合物，以及获取它们的方法、它们的用途，以及它们还原为吡咯并利用所得的吡咯、吡啶二氮杂吡咯和寡吡咯化合物的用途。本发明特别涉及作为药物的用途，特别是用于治疗癌症、细菌感染或寄生虫感染等病理情况，以及在材料、环境、电子和光学领域的应用。

  公开号：

  US20100004443A1
• 作为产物：
  描述：

  3-pyridin-2-yl-4,5-dihydro-1H-pyridazin-6-one 在 selenium(IV) oxide 作用下， 以 乙二醇甲醚 为溶剂， 反应 3.0h， 以58%的产率得到6-(吡啶-2-基)-2,3-二氢吡嗪-3-酮
  参考文献：
  名称：

  Powell, Paul; Sosabowski, Michael H., Journal of Chemical Research, Miniprint, 1995, # 8, p. 1840 - 1852

  摘要：

  DOI：

文献信息

• 6- And 8-heteroaryl-1,2,4-triazolo[4,3-b]pyridazines
  申请人：American Cyanamid Company

  公开号：US04260756A1

  公开（公告）日：1981-04-07

  This disclosure describes novel 6- and 8-heteroaryl and substituted 6- and 8-heteroaryl-1,2,4-triazolo[4,3-b]-pyridazines and their use as agents for treating anxiety.

  这份披露描述了新颖的6-和8-杂芳基及取代的6-和8-杂芳基-1,2,4-三唑并[4,3-b]-吡啶嗪，以及它们作为治疗焦虑症的药剂的用途。
• Pyridazine and Pyrrole Compounds, Processes For Obtaining Them and Uses
  申请人：Dubreuil Didier Max

  公开号：US20100298562A1

  公开（公告）日：2010-11-25

  The present invention relates to nonlinear oligopyridazine compounds, to processes for obtaining them, to their uses, and also to their reduction to oligopyrroles and to the uses of the pyridazinylpyrrole and oligopyrrole compounds obtained. The invention relates in particular to the uses as medicaments, in particular for treating pathologies such as cancer, bacterial infections or parasitic infections, and also the uses in the materials, environmental, electronics and optics field.

  本发明涉及非线性寡吡啶化合物，以及获得它们的方法，它们的用途，以及将它们还原为寡吡咯和所获得的吡啶基吡咯和寡吡咯化合物的用途。该发明特别涉及用作药物的用途，特别是用于治疗癌症、细菌感染或寄生虫感染等病理的用途，以及在材料、环境、电子和光学领域的用途。
• One-Pot Preparation of 6-Substituted 3(2<i>H</i>)-Pyridazinones from Ketones
  作者：W. J. Coates、A. Mckillop

  DOI：10.1055/s-1993-25861

  日期：——

  A one-pot process for the preparation of 6-phenyl-3(2H)-pyridazinone from acetophenone and glyoxylic acid has been investigated and shown to have wide utility in the preparation of 6- and 5,6-substituted 3(2H)-pyridazinones. Limitations to the process encountered with 2′-hydroxyacetophenone and with basic heteroaromatic ketones have been overcome, and the processes described offer the rapid and efficient synthesis of many 6-substituted pyridazinones from readily available ketones.

  一种利用乙酰苯和乙醛酸制备6-苯基-3(2H)-吡哒嗪酮的一锅法工艺已被研究，并证明在制备6-和5,6-取代的3(2H)-吡哒嗪酮方面具有广泛应用。该工艺解决了遇到2′-羟基乙酰苯和基本杂芳香酮时的局限性问题，并提供了一种快速高效合成多种6-取代吡哒嗪酮的方法，原料为易得的酮类。
• Synthesis and Biological Evaluation of Novel Neuroprotective Pyridazine Derivatives as Excitatory Amino Acid Transporter 2 (EAAT2) Activators
  作者：Alessia Chelini、Simone Brogi、Marco Paolino、Angela Di Capua、Andrea Cappelli、Gianluca Giorgi、Mersedeh Farzad、Lorenzo Di Cesare Mannelli、Laura Micheli、Carla Ghelardini、Maurizio Anzini

  DOI：10.1021/acs.jmedchem.7b00383

  日期：2017.6.22

  LDN-212320 (3) was found to be a potent EAAT2 activator at a translational level, restoring the normal clearance of glutamate and providing neuronal protection. Since the pharmacologic activation of EAAT2 represents a valuable strategy to relieve neuropathic pain, we synthesized novel activators (4a–f) of EAAT2. Among them 4f, analyzed in comparison with 3 by different paradigms in a rat model of oxaliplatin-induced

  发现LDN-212320（3）在翻译水平上是有效的EAAT2激活剂，可恢复谷氨酸的正常清除率并提供神经元保护作用。由于EAAT2的药理学激活代表了缓解神经性疼痛的重要策略，因此我们合成了EAAT2的新型激活剂（4a – f）。其中4f与奥沙利铂诱发的神经性疼痛大鼠模型中的不同范例进行了比较，与3相比进行了分析，结果显示，较好的抗过敏药谱能够完全抵消奥沙利铂诱发的神经性疼痛。
• Nitrile Oxide [3 + 2] Cycloaddition: Application to the Synthesis of 6-Substituted 3(2<i>H</i>)-Pyridazinones and 6-Substituted 4,5-Dihydro-4-hydroxy-3(2<i>H</i>)-pyridazinones
  作者：P. G. Baraldi、A. Bigoni、B. Cacciari、C. Caldari、S. Manfredini、G. Spalluto

  DOI：10.1055/s-1994-25663

  日期：——

  An efficient method for the preparation of 6-substituted 3(2H)-pyridazinones and 6-substituted 4,5-dihydro-4-hydroxy-3(2H)-pyridazinones starting from 3,5-disubstituted 4,5-dihydroisoxazoles is described. N-O bond cleavage of the isoxazoline ring promoted by molybdenum hexacarbonyl or by catalytic hydrogenation afforded the α-hydroxy γ-keto esters 4a-f which were converted into 6-substituted 4,5-dihydro-4-hydroxy-3(2H)-pyridazinones 5a-f or 6-substituted 3(2H)-pyridazinones 6a-f on treatment with hydrazine hydrate at room temperature or reflux in high yield starting from 4a-f. The flexibility of this protocol has been demonstrated by the synthesis of the C-nucleoside 7 starting from the known β-ribofu-ranosylnitromethane 8. Moreover, an intramolecular version of this methodology has been developed to prepare the known antiulcer tricyclic 3(2H)-pyridazinone 12.

  描述了一种从3,5-二取代的4,5-二氢异噁唑出发，高效制备6-取代的3(2H)-吡嗪酮和6-取代的4,5-二氢-4-羟基-3(2H)-吡嗪酮的方法。通过六羰基钼或催化氢化促进异噁唑啉环的N-O键断裂，获得了α-羟基γ-酮酯4a-f，这些酯在室温或回流条件下与水合肼反应生成6-取代的4,5-二氢-4-羟基-3(2H)-吡嗪酮5a-f或6-取代的3(2H)-吡嗪酮6a-f，且收率较高。该协议的灵活性通过从已知的β-核糖硝基甲烷8合成C-核糖苷7得到了验证。此外，还开发了一种分子内版本的方法来制备已知的抗溃疡三环3(2H)-吡嗪酮12。