6-phenyl-5-hydroxymethyl-4,5-dihydro-3(2H)-pyridazinine acetate | 132814-17-6

• 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: 6-phenyl-5-hydroxymethyl-4,5-dihydro-3(2H)-pyridazinine acetate
• 英文别名: 6-phenyl-5-hydroxymethyl-4,5-dihydro-2H-pyridazin-3-one acetate；3(2H)-Pyridazinone, 5-[(acetyloxy)methyl]-4,5-dihydro-6-phenyl-；(6-oxo-3-phenyl-4,5-dihydro-1H-pyridazin-4-yl)methyl acetate
• CAS: 132814-17-6
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: IKEVDKTYXIUPPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-phenyl-5-hydroxymethyl-4,5-dihydro-3(2H)-pyridazinine acetate 在 溴 、 乙酸酐 、 溶剂黄146 作用下， 反应 3.0h， 以54%的产率得到5-bromomethyl-6-phenyl-3(2H)-pyridazinone
  参考文献：
  名称：

  哒嗪衍生物。XIX：6-苯基-3（2 H）-哒嗪酮系统中5位的官能化研究†

  摘要：

  为了寻找新的血小板聚集抑制剂，制备了一系列在哒嗪酮环的5位带有不同取代基的6-苯基-3（2 H）-哒嗪酮。根据光谱法确定最终化合物的结构。

  DOI：

  10.1002/jhet.5570360426
• 作为产物：
  描述：

  5-羟基甲基-6-苯基-4,5-二氢-3(2H)-哒嗪酮 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以100%的产率得到6-phenyl-5-hydroxymethyl-4,5-dihydro-3(2H)-pyridazinine acetate
  参考文献：
  名称：

  哒嗪衍生物。XIX：6-苯基-3（2 H）-哒嗪酮系统中5位的官能化研究†

  摘要：

  为了寻找新的血小板聚集抑制剂，制备了一系列在哒嗪酮环的5位带有不同取代基的6-苯基-3（2 H）-哒嗪酮。根据光谱法确定最终化合物的结构。

  DOI：

  10.1002/jhet.5570360426

文献信息

• Ureido-Pyridazinone Derivatives: Insights into the Structural and Conformational Properties for STAT3 Inhibition
  作者：Fiorella Meneghetti、Stefania Villa、Daniela Masciocchi、Daniela Barlocco、Lucio Toma、Dong-Cho Han、Byoung-Mog Kwon、Naohisa Ogo、Akira Asai、Laura Legnani、Arianna Gelain

  DOI：10.1002/ejoc.201500599

  日期：2015.8

  Three new ureido-pyridazinone derivatives, which are structurally related to the known STAT3 inhibitor AVS-0288, were designed by taking into account the structure–activity relationships determined for several ureido-oxadiazole derivatives previously studied by our group. Their synthesis was first attempted through suitable 5-aminopyridazinone intermediates (6a and 6b), which molecular structures were

  考虑到我们小组先前研究的几种脲基-恶二唑衍生物的构效关系，设计了三种新的脲基-哒嗪酮衍生物，它们在结构上与已知的 STAT3 抑制剂 AVS-0288 相关。它们的合成首先通过合适的 5-氨基哒嗪酮中间体（6a 和 6b）尝试合成，其分子结构通过 6a 的 X 射线衍射数据得到证实。胺官能化不成功，因此，设计了替代方法。双荧光素酶和基于 AlphaScreen 的测定被用来测试它们的活性。在建模研究的基础上对获得的数据进行了合理化，该研究将我们的注意力集中在脲基部分的几何偏好上。计算结果似乎表明 1,2,
• Pyridazines. XIII. Synthesis of 6-Aryl-5-Oxygenated Substituted-3(2H)-Pyridazinones and Evaluation as Platelet Aggregation Inhibitors.
  作者：Reyes LAGUNA、Belen RODRIGUEZ-LINARED、Ernesto CANO、Isabel ESTEVEZ、Enrique RAVINA、Eddy SOTELO

  DOI：10.1248/cpb.45.1151

  日期：——

  evaluated in vitro for inhibition of platelet aggregation induced by adenosine 5'-diphosphate (ADP), thrombin and collagen. All the tested compounds (except 8 and 9) inhibited platelet aggregation in a dose-dependent manner. The IC50 of the most active substance, compound 2b, was around 60 microM against ADP and collagen as inducers. The inhibition of platelet aggregation caused by test compounds was dependent

  已经合成了几种6-芳基-5-加氧的取代的哒嗪酮，并在体外评估了对5'-二磷酸腺苷（ADP），凝血酶和胶原蛋白诱导的血小板聚集的抑制作用。所有测试的化合物（8和9除外）均以剂量依赖的方式抑制血小板凝集。活性最高的物质（化合物2b）对ADP和胶原诱导剂的IC50约为60 microM。受试化合物对血小板聚集的抑制作用取决于功能在5位的氧化程度，IC50值的顺序为R-OH（2a，b，5）
• Efficient Aromatization of 4,5-Dihydro-3(2<i>H</i>)-Pyridazinones Substituted at 5 Position by Using Anhydrous Copper (II) Chloride
  作者：Eddy Sotelo、Enrique Raviña

  DOI：10.1080/00397910008087285

  日期：2000.1

  An efficient conversion of 5-substituted-4,5-dihydro-3(2H)-pyridazinones into their corresponding dehydrogenated derivatives was achieved by treatment with anhydrous copper(II) chloride in acetonitrile.
• Pyridazine Derivatives, IX. Synthesis of 2H-Pyridazin-3-ones with Aroylpiperazinyl Groups
  作者：Enrique Ravina、Carmen Teran、Lourdes Santana、Neftali Garcia、Isabel Estevez

  DOI：10.3987/com-90-5493

  日期：——

  -Several 2H-pyridazin-3-ones with phenyl- or 2-furoylpiperazinyl group, have been prepared. 6-Phenyl-5-(N4-aroyl-N1-piperazinyl)-2H-pyridazin-3-ones were obtained by nucleophilic substitution of the chlorine atom of 6-phenyl-5-chloro-2H-pyridazin-3-one or alternatively, by aroylation of N1-piperazinyl-2h-pyridazin-3-one. Also, 6-phenyl-5-(N4-aroyl-N1-piperazinylmethyl)-2H-pyridazin-3-ones were prepared by displacement of the bromine in 6-phenyl-5-bromomethyl-2h-pyridazin-3-one.
• RAVINA, ENRIQUE;TERAN, CARMEN;SANTANA, LOURDES;GARCIA, NEFTALI;ESTEVES, I+, HETEROCYCLES, 31,(1990) N1, C. 1967-1974
  作者：RAVINA, ENRIQUE、TERAN, CARMEN、SANTANA, LOURDES、GARCIA, NEFTALI、ESTEVES, I+

  DOI：——

  日期：——