(E)-4,5-dichloro-2-styrylpyridazin-3(2H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4,5-dichloro-2-styrylpyridazin-3(2H)-one
• 英文别名: trans-4,5-dichloro-2-styrylpyridazin-3(2H)-one；trans-4,5-dichloro-2-styrylpyridazine-3(2H)-one；4,5-dichloro-2-[(E)-2-phenylethenyl]pyridazin-3-one
• 化学式: C₁₂H₈Cl₂N₂O
• 分子量: 267.114
• InChiKey: BGNRQDNVSBXOSQ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  在 氯化亚砜 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (E)-4,5-dichloro-2-styrylpyridazin-3(2H)-one
  参考文献：
  名称：

  Fluorescent 2-styrylpyridazin-3(2H)-one derivatives as probes targeting amyloid-beta plaques in Alzheimer’s disease

  摘要：

  Amyloid plaques, which are primarily composed of aggregated amyloid-beta (A beta) peptide, are the neuropathological hallmarks of Alzheimer's disease (AD). Fluorescent markers containing 2-styrylpyridazin-3(2H)-ones were developed to detect intracellular aggregated A beta peptides. Nine compounds exhibited a greater than 10-fold increase of in emission spectra before and after mixing with A beta aggregates compared with before mixing. Among these compounds, compound 9n exhibited the highest affinity for A beta aggregates (K-d = 1.84 mu M) and selectively stained both aggregated intracellular A beta and A beta plaques in the transgenic AD model mice (APP/PS1). These preliminary results indicate that 2-styrylpyridazin-3(2H)-one derivatives are promising alternative fluorescence imaging agent for the study of AD. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.068

文献信息

• Substituent-dependence of photophysical properties of<i>trans</i>-2-styrylpyridazin-3(2<i>H</i>)-ones
  作者：Bo Ram Kim、Su-Dong Cho、Hyung-Geun Lee、Heung-Seop Yim、Min-Jung Kim、Jaeyoung Hwang、Song-Eun Park、Jeum-Jong Kim、Kwang-Ju Jung、Yong-Jin Yoon

  DOI：10.1002/jhet.137

  日期：2009.7

  trans-2-(p-substituted-styryl)pyridazin-3(2H)-ones and , the magnitude of the solvatochromic shifts and the shape of the fluorescence spectra depend on the number and/or the position of substituents in benzene ring. The emission maximum of trans-2-styrylpyridazin-3(2H)-ones involving the electron-donating group is larger than one of trans-2-styrylpyridazin-3(2H)-ones involving the electron-withdrawing group

  反式-2-苯乙烯基哒嗪-3（2 H）-ones的光物理行为 在很大程度上取决于THF中苯环上取代基的数量和位置， 二氯甲烷，乙腈和甲醇。的吸收光谱在对位含有给电子取代基的电子显示出红移，而含有吸电子取代基的化合物显示出蓝移。对于反式-2-（p-取代的苯乙烯基）哒嗪-3（2 H）- 和 溶剂变色位移的大小和荧光光谱的形状取决于苯环中取代基的数目和/或位置。发射最大值的反式-2- styrylpyridazin-3（2 ħ） -酮涉及供电子基团是比1大的反式-2- styrylpyridazin-3（2 ħ） -酮涉及吸电子基团在苯基戒指。发射最大值的大小大致与苯环取代基的相对吸电子能力平行。J.杂环化​​学，（2009）。
• Synthesis and photochemical properties of<i>trans</i>‐2‐(2‐aryl‐ or heteroarylvinyl)‐4,5‐dichloropyridazin‐3(2<i>H</i>)‐ones
  作者：Heung‐Seop Yim、Mi‐Ra Kim、Gi‐Hyeon Sung、Hyun‐A Chung、Jin‐Kook Lee、Sang‐Gyeong Lee、Yong‐Jin Yoon

  DOI：10.1002/jhet.5570450126

  日期：2008.1

  trans-2-(2-Aryl- or heteroarylvinyl)-4,5-dichloropyridazin-3(2H)-ones 3 were synthesized from 4,5-dichloropyridazin-3(2H)-one via 2 step. The photochemical behavior of 3 in THF, methylene chloride, acetonitrile and methanol is dependent on the kind of aryl or heterocyclic ring and the solvent polarity

  反式-2-（2-芳基-或heteroarylvinyl）-4,5-二氯哒嗪-3（2 H ^） -酮3从4,5-二氯哒嗪-3（2合成ħ） -酮通过2步骤。3在THF，二氯甲烷，乙腈和甲醇中的光化学行为取决于芳基或杂环的种类以及溶剂的极性
• METHOD FOR DETECTING AMYLOID AGGREGATES USING STYRYLPYRIDAZINE-ONE DERIVATIVES
  申请人：KOREA ATOMIC ENERGY RESEARCH INSTITUTE

  公开号：US20140134109A1

  公开（公告）日：2014-05-15

  The present invention relates to a composition for detecting beta amyloid aggregates and a composition for diagnosing beta amyloid aggregation disease, comprising a 2-styrilpyridizine-3(2H)-one derivative or its pharmaceutically acceptable salt, to a diagnostic kit for diagnosing beta amyloid aggregation disease comprising said composition and to a method for detecting beta amyloid aggregates using said compositions to provide information for beta amyloid aggregation disease diagnosis.

  本发明涉及一种用于检测β淀粉样聚集物和诊断β淀粉样聚集病的组合物，包括2-苯基吡啶嗪-3(2H)-酮衍生物或其药用可接受的盐，以及用于诊断β淀粉样聚集病的诊断试剂盒，包括上述组合物，以及使用上述组合物检测β淀粉样聚集物的方法，以提供β淀粉样聚集病诊断的信息。
• Synthesis and photophysical properties of<i>N</i>-styrylazinones
  作者：Su-Dong Cho、Jaeyoung Hwang、Ho-Kyun Kim、Heung-Sup Yim、Jeum-Jong Kim、Sang-Gyeong Lee、Yong-Jin Yoon

  DOI：10.1002/jhet.5570440435

  日期：2007.7

  Abstractmagnified imageN‐Styrylazinones and 1‐styrylbenzotriazine were synthesized, and their photophysical properties were investigated. (Z)‐ and/or (E)‐N‐Styrylazinones (or azine) 4 were prepared from the corresponding heterocycles 1 and benzaldehyde (3) by four methods. The absorption maxima of (Z)‐ and/or (E)‐4a‐4j were measured in four solvents. Their absorption maxima showed a moderate dependence upon solvents. The absorption maxima of (Z)‐isomers were blue‐shifted as compared the corresponding (E)‐isomers. Emission maxima, fluorescence band half‐widths, 0,0 transition energies, Stokes shifts, and quantum yields of (Z)‐ and/or (E)‐4a, 4b, 4d, 4e and 4j were measured in organic solvents. The fluorescence spectra show moderate solvatochroism. The fluorescence properties of N‐styrylheterocycles vary with every heterocycles.
• US8961937B2
  申请人：——

  公开号：US8961937B2

  公开（公告）日：2015-02-24