2-(2-chlorophenyl)-6-(3-chlorophenyl)pyridazin-3(2H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(2-chlorophenyl)-6-(3-chlorophenyl)pyridazin-3(2H)-one
• 英文别名: 2-(2-Chlorophenyl)-6-(3-chlorophenyl)pyridazin-3-one
• 化学式: C₁₆H₁₀Cl₂N₂O
• 分子量: 317.174
• InChiKey: HBYNIAFJWJUDSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2-氯苯基)-肼 在 四(三苯基膦)钯 、 caesium carbonate 、 三氯氧磷 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-(2-chlorophenyl)-6-(3-chlorophenyl)pyridazin-3(2H)-one
  参考文献：
  名称：

  p38 MAP kinase inhibitors. Part 6: 2-Arylpyridazin-3-ones as templates for inhibitor design

  摘要：

  p38 inhibitors based on 3,4-dihydropyrido[4,3-d]pyrimidazin-2-one template were synthesized and their SAR explored. Benchmark compounds 30, 35, and 36 were found to be potent against the enzyme. Crystal structure of p38 in complex with 30 indicated a key pi-stacking interaction with the pendant tyrosine residue-35 in the glycine-rich loop.

  DOI：

  10.1016/j.bmcl.2006.08.074

文献信息

• Rational Design, Green Synthesis, and Initial Evaluation of a Series of Full-Color Tunable Fluorescent Dyes Enabled by the Copper-Catalyzed N-Arylation of 6-Phenyl Pyridazinones and Their Application in Cell Imaging
  作者：Lei Liang、Wei Wang、Jun Wu、Fengrong Xu、Yan Niu、Bo Xu、Ping Xu

  DOI：10.1002/chem.201302495

  日期：2013.10.4

  pyridazinones were synthesized rationally by this methodology as full‐color tunable fluorescent agents (426–612 nm). The N2 position of pyridazinones was modified by different aryl group such as benzothiazole, N,N‐dimethylaniline, 3‐quinoline, 4‐isoquinoline and 2‐thiophene, resulting in a series of full‐color tunable fluorescent reagents. Meanwhile, the effects of electron‐donating and electron‐withdrawing

  人们对N-杂芳烃的过渡金属催化芳基化的应用，优化和发展有着广泛的兴趣，以发现全色可调荧光核心框架。受哒嗪酮在有机合成和药物化学中的多种作用的启发，本文报道了一种简单有效的铜催化交叉偶联反应，用于纯净水中哒嗪酮的N-官能化。为了实现吡嗪酮和有机卤化物在水相中的有效转化，通过合理设计研究了一系列由不同席夫碱配体组成的铜salen配合物。在候选物中确定了最终选择的经过微调的亲水性和亲脂性之间的平衡，这为广泛的哒嗪酮和有机卤化物的反应提供了出色的活性。更重要的是，通过这种方法可以合理地合成N取代的哒嗪酮类产品，作为全色可调荧光剂（426–612 nm）。哒嗪酮的N2位置被不同的芳基（如苯并噻唑）修饰，N，N-二甲基苯胺，3-喹啉，4-异喹啉和2-噻吩，产生了一系列全色可调荧光试剂。同时，还研究了6-取代苯环的给电子基团和吸电子基团的作用，以优化荧光性质。这些荧光核心框架已在几种细胞系中作为荧光染料
• Relay Catalysis by a Multifunctional Cu Catalyst in a Tandem Dehydro-/Dehalogenation Sequence along with N-Arylation
  作者：Lei Liang、Wei Wang、Fengrong Xu、Yan Niu、Qi Sun、Ping Xu

  DOI：10.1021/ol401105x

  日期：2013.6.7

  A Cu-catalyzed tandem dehydrogenation/dehalogenation sequential reaction along with N-arylation has been developed for the synthesis of pyridazinone derivatives in an aerobic and aqueous environment. To achieve the transformation of three chemical bonds in a one-pot reaction, a multifunctional copper catalyst was used which afforded excellent activity, high selectivity, and recyclability. The catalytic system consists of a water-soluble Cusalen complex and Na2CO3 in neat water and an air atmosphere.
• p38 MAP kinase inhibitors. Part 6: 2-Arylpyridazin-3-ones as templates for inhibitor design
  作者：Swaminathan R. Natarajan、Stephen T. Heller、Kiyean Nam、Suresh B. Singh、Giovanna Scapin、Sangita Patel、James E. Thompson、Catherine E. Fitzgerald、Stephen J. O’Keefe

  DOI：10.1016/j.bmcl.2006.08.074

  日期：2006.11

  p38 inhibitors based on 3,4-dihydropyrido[4,3-d]pyrimidazin-2-one template were synthesized and their SAR explored. Benchmark compounds 30, 35, and 36 were found to be potent against the enzyme. Crystal structure of p38 in complex with 30 indicated a key pi-stacking interaction with the pendant tyrosine residue-35 in the glycine-rich loop.