6-(naphthalen-2-yl)pyridazin-3(2H)-one | 24737-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(naphthalen-2-yl)pyridazin-3(2H)-one
• 英文别名: 6-naphthalen-2-yl-2H-pyridazin-3-one；6-[2]naphthyl-2H-pyridazin-3-one；6-[2]Naphthyl-2H-pyridazin-3-on；6--3-oxo-2.3-dihydro-pyridazin；6-(2-naphthyl)pyridazin-3(2H)-one；3-naphthalen-2-yl-1H-pyridazin-6-one
• CAS: 24737-91-5
• 化学式: C₁₄H₁₀N₂O
• mdl: MFCD12531088
• 分子量: 222.246
• InChiKey: WGLIXRXOERJHDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  6-(naphthalen-2-yl)pyridazin-3(2H)-one 在 铁粉 、 caesium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Discovery of novel 2,6-disubstituted pyridazinone derivatives as acetylcholinesterase inhibitors

  摘要：

  2,6-Disubstituted pyridazinone 4 was identified by HTS as a novel acetylcholinesterase (AChE) inhibitor. Under SAR development, compound 17e stood out as displaying high AChE inhibitory activity and AChE/butyrylcholinesterase (BuChE) selectivity in vitro. Docking studies revealed that 17e might interact with the catalytic active site (CAS) and the peripheral anionic site (PAS) simultaneously. Based on this novel binding information, 6-ortho-tolylamino and N-ethyl-N-isopropylacetamide substituted piperidine were disclosed as new PAS and CAS binders. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.056
• 作为产物：
  描述：

  Ethyl 2-benzoyl-4-naphthalen-2-yl-4-oxobut-2-enoate 在 一水合肼 作用下， 以 叔丁醇 为溶剂， 以155.4 mg的产率得到6-(naphthalen-2-yl)pyridazin-3(2H)-one
  参考文献：
  名称：

  Unexpected C–C Bond Cleavage: A Route to 3,6-Diarylpyridazines and 6-Arylpyridazin-3-ones from 1,3-Dicarbonyl Compounds and Methyl Ketones

  摘要：

  An unexpected C-C bond cleavage has been revealed in the absence of metal. This observation has been exploited to develop an efficient approach toward 3,6-iarylpyridazines and 6-arylpyridazin-3-ones from simple and commercially available 1,3-dicarbonyl compounds and methyl ketones.

  DOI：

  10.1021/jo301751e

文献信息

• Hydrazinderivate der Phtalazin- und Pyridazinreihe
  作者：J. Druey、B. H. Ringier

  DOI：10.1002/hlca.19510340122

  日期：——

  Es werden Hydrazinoderivate des Phtalazins und des Pyridazins beschrieben, über deren pharmakologisches Interesse an anderer Stelle berichtet worden ist. Die am Grundtypus vorgenommenen chemischen Abwandlungen betreffen die Substitutionen am heterocyclischen oder aromatischen Ring, den Ersatz des aromatischen Kerns durch den Pyridinring und schliesslich Veränderungen am Hydrazinrest.

  描述了酞嗪和哒嗪的肼基衍生物，其药理学兴趣已在其他地方报道。基本类型的化学修饰涉及杂环或芳香环上的取代，吡啶环取代芳香核，最后改变肼残基。
• Scope and limitation of propylene carbonate as a sustainable solvent in the Suzuki–Miyaura reaction
  作者：Andrea Czompa、Balázs László Pásztor、Jennifer Alizadeh Sahar、Zoltán Mucsi、Dóra Bogdán、Krisztina Ludányi、Zoltán Varga、István M. Mándity

  DOI：10.1039/c9ra07044c

  日期：——

  reaction is one of the most used transformations in drug research. Thus making this reaction more sustainable is of considerable current interest. Here we show that propylene carbonate (PC) can be used as a solvent for the Suzuki–Miyaura reaction. PC is one of the greenest solvents since it is synthesized under green conditions by the use of carbon dioxide in the air. All reactions proceeded well and good

  Suzuki-Miyaura 反应是药物研究中最常用的转化之一。因此，使这种反应更具可持续性是当前相当大的兴趣。在这里，我们表明碳酸亚丙酯 (PC) 可用作 Suzuki-Miyaura 反应的溶剂。PC 是最环保的溶剂之一，因为它是在绿色条件下通过使用空气中的二氧化碳合成的。所有反应都进行得很好并且对于联芳基产物观察到良好或优异的产率。尽管如此，在哒嗪酮的情况下，观察到含有2-羟丙基链的副产物。重要的是，这一事实允许分离在显着绿色条件下产生的几种新化合物。
• Discovery of Novel Pyridazine-Tethered Sulfonamides as Carbonic Anhydrase II Inhibitors for the Management of Glaucoma
  作者：Haytham O. Tawfik、Mohamed M. Saleh、Andrea Ammara、Eman F. Khaleel、Rehab Badi、Yomna T. T. Khater、Rabab A. Rasheed、Ahmed A. Attia、Salma M. Hefny、Eslam B. Elkaeed、Alessio Nocentini、Claudiu T. Supuran、Wagdy M. Eldehna、Moataz A. Shaldam

  DOI：10.1021/acs.jmedchem.3c02279

  日期：2024.1.25

  neuropathic condition, glaucoma can cause lifelong blindness if left untreated. Novel phenylpyridazine-tethered sulfonamides were designed as selective inhibitors for carbonic anhydrase (CA) isoform II to find effective therapeutic agents for glaucoma. Subsequently, the target inhibitors were synthesized and assessed for their inhibitory action against cytosolic CA I and II. Interestingly, the synthesized

  作为一种进行性神经病变，青光眼如果不及时治疗可能会导致终身失明。新型苯基哒嗪系磺酰胺被设计为碳酸酐酶 (CA) 异构体 II 的选择性抑制剂，以寻找青光眼的有效治疗药物。随后，合成了目标抑制剂并评估了它们对胞质 CA I 和 II 的抑制作用。有趣的是，合成的分子对 CA I 的抑制效果很差，同时对 CA II 的亚纳摩尔效力较低。化合物7c具有最强的活性 (IC 50 = 0.63 nM)，对 CA II 具有高选择性（是乙酰唑酰胺选择性的 605 倍）。此外，化合物7c还在青光眼体内模型中显示出显着的体内眼压降低特性。此外，利用分子对接方法在分子水平上评估了化合物7c与 CA II 的结合。
• Unexpected C–C Bond Cleavage: A Route to 3,6-Diarylpyridazines and 6-Arylpyridazin-3-ones from 1,3-Dicarbonyl Compounds and Methyl Ketones
  作者：Qinghe Gao、Yanping Zhu、Mi Lian、Meicai Liu、Jingjing Yuan、Guodong Yin、Anxin Wu

  DOI：10.1021/jo301751e

  日期：2012.11.2

  An unexpected C-C bond cleavage has been revealed in the absence of metal. This observation has been exploited to develop an efficient approach toward 3,6-iarylpyridazines and 6-arylpyridazin-3-ones from simple and commercially available 1,3-dicarbonyl compounds and methyl ketones.
• Discovery of novel 2,6-disubstituted pyridazinone derivatives as acetylcholinesterase inhibitors
  作者：Weiqiang Xing、Yan Fu、Zhangxing Shi、Dong Lu、Haiyan Zhang、Youhong Hu

  DOI：10.1016/j.ejmech.2013.01.056

  日期：2013.5

  2,6-Disubstituted pyridazinone 4 was identified by HTS as a novel acetylcholinesterase (AChE) inhibitor. Under SAR development, compound 17e stood out as displaying high AChE inhibitory activity and AChE/butyrylcholinesterase (BuChE) selectivity in vitro. Docking studies revealed that 17e might interact with the catalytic active site (CAS) and the peripheral anionic site (PAS) simultaneously. Based on this novel binding information, 6-ortho-tolylamino and N-ethyl-N-isopropylacetamide substituted piperidine were disclosed as new PAS and CAS binders. (c) 2013 Elsevier Masson SAS. All rights reserved.