3-amino-6-<3,4-(methylenedioxy)phenyl>pyridazine | 143268-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-amino-6-<3,4-(methylenedioxy)phenyl>pyridazine
• 英文别名: 3-amino-6-(3,4-methylenedioxy phenyl)pyridazine；6-(1,3-Benzodioxol-5-yl)pyridazin-3-amine
• CAS: 143268-21-7
• 化学式: C₁₁H₉N₃O₂
• 分子量: 215.211
• InChiKey: QLEVGPGEDIZEPN-UHFFFAOYSA-N

物化性质

• 熔点：
  191-193 °C
• 沸点：
  472.1±45.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-amino-6-<3,4-(methylenedioxy)phenyl>pyridazine 在 氢溴酸 、 N,N-二甲基甲酰胺 作用下， 以 溶剂黄146 为溶剂， 反应 26.0h， 生成 2-(3-caboxypropyl)-3-imino-6-[3,4-(methylenedioxy)phenyl]-2,3-dihydropyridazine hydrobromide
  参考文献：
  名称：

  muscimol或thiomuscimol与氨基哒嗪的缩合产生GABA-A拮抗剂。

  摘要：

  通过将6-芳基-3-氨基哒嗪与（氯甲基）异恶唑或（氯甲基）异噻唑衍生物进行N 2烷基化反应，制备了氨基官能团在local胺基体系中离域的十种麝香酚和硫代麝香酚类似物。这些muscimol和thiomuscimol衍生物显示出对GABA-A受体的强效结合特性（它们取代了[3H] GABA和[3H] gabazine）并在静脉注射后引起惊厥。它们与我们小组提出的GABA-A拮抗剂模型药效基团非常吻合，并显示出与哒嗪基-GABA相似的结构活性图谱。

  DOI：

  10.1021/jm00100a015
• 作为产物：
  描述：

  3-hydrazino-6-<3,4-(methylenedioxy)phenyl>pyridazine 在 镍 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以52%的产率得到3-amino-6-<3,4-(methylenedioxy)phenyl>pyridazine
  参考文献：
  名称：

  muscimol或thiomuscimol与氨基哒嗪的缩合产生GABA-A拮抗剂。

  摘要：

  通过将6-芳基-3-氨基哒嗪与（氯甲基）异恶唑或（氯甲基）异噻唑衍生物进行N 2烷基化反应，制备了氨基官能团在local胺基体系中离域的十种麝香酚和硫代麝香酚类似物。这些muscimol和thiomuscimol衍生物显示出对GABA-A受体的强效结合特性（它们取代了[3H] GABA和[3H] gabazine）并在静脉注射后引起惊厥。它们与我们小组提出的GABA-A拮抗剂模型药效基团非常吻合，并显示出与哒嗪基-GABA相似的结构活性图谱。

  DOI：

  10.1021/jm00100a015

文献信息

• Microwave-enhanced synthesis of 2,3,6-trisubstituted pyridazines: application to four-step synthesis of gabazine (SR-95531)
  作者：Navnath Gavande、Graham A. R. Johnston、Jane R. Hanrahan、Mary Chebib

  DOI：10.1039/c0ob00004c

  日期：——

  Microwave-enhanced, highly efficient protocols for the synthesis of synthetically and biologically important 2,3,6-trisubstituted pyridazine architectures have been developed by sequential amination/Suzuki coupling/alkylation reactions. This powerful strategy is an economical and highly chemoselective protocol for the synthesis of diversified pyridazines. The total synthesis of gabazine (SR-95531)

  微波增强的，高效的合成和生物学上重要的2,3,6-三取代合成方案 哒嗪通过顺序胺化/ Suzuki偶联/烷基化反应已经开发出各种结构。这种强大的策略是用于合成多种哒嗪的经济且高度化学选择性的方案。川ab嗪的全合成（SR-95531）可通过四个步骤采用多功能策略实现，总收率达到73％。
• A Convenient 3-Step Synthesis of 3-Acetamido-6-arylpyridazines Directed to Novel Y5 Receptor Antagonist.
  作者：Sébastien Guéry、Yveline Rival、Camille-Georges Wermuth、Pierre Renard、Jean-Albert Boutin

  DOI：10.1248/cpb.50.636

  日期：——

  A 3-step synthesis of 3-acetamido-6-arylpyridazines as potential NPY5 antagonists.

  3-乙酰氨基-6-芳基哒嗪作为潜在的NPY5拮抗剂的3步合成。
• Competitive antagonism of insect GABA receptors by iminopyridazine derivatives of GABA
  作者：Mohammad Mostafizur Rahman、Yuki Akiyoshi、Shogo Furutani、Kazuhiko Matsuda、Kenjiro Furuta、Izumi Ikeda、Yoshihisa Ozoe

  DOI：10.1016/j.bmc.2012.07.049

  日期：2012.10

  A series of 4-(6-imino-3-aryl/heteroarylpyridazin-1-yl) butanoic acids were synthesized and examined for antagonism of GABA receptors from three insect species. When tested against small brown planthopper GABA receptors, the 3,4-methylenedioxyphenyl and the 2-naphthyl analogues showed complete inhibition of GABA-induced fluorescence changes at 100 mu M in assays using a membrane potential probe. Against common cutworm GABA receptors, these analogues displayed approximately 86% and complete inhibition of GABA-induced fluorescence changes at 100 mu M, respectively. The 4-biphenyl and 4-phenoxyphenyl analogues showed moderate inhibition at 10 mu M in these receptors, although the inhibition at 100 mu M was not complete. Against American cockroach GABA receptors, the 4-biphenyl analogue exhibited the greatest inhibition (approximately 92%) of GABA-induced currents, when tested at 500 mu M using a patch-clamp technique. The second most active analogue was the 2-naphthyl analogue with approximately 85% inhibition. The 3-thienyl analogue demonstrated competitive inhibition of cockroach GABA receptors. Homology modeling and ligand docking studies predicted that hydrophobic 3-substituents could interact with an accessory binding site at the orthosteric binding site. (C) 2012 Elsevier Ltd. All rights reserved.
• Efficient one-step synthesis of 3-amino-6-arylpyridazines
  作者：Sébastien Guery、Isabelle Parrot、Yveline Rival、Camille G Wermuth

  DOI：10.1016/s0040-4039(01)00134-4

  日期：2001.3

  Starting from the commercially available 3-amino-6-chloropyridazine, 3-amino-6-arylpyridazines were prepared in good yields by means of a Suzuki cross-coupling reaction avoiding the somewhat lengthy four-step classic synthesis. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Condensation of muscimol or thiomuscimol with aminopyridazines yields GABA-A antagonists
  作者：Anita Melikian、Gilbert Schlewer、Jean Pierre Chambon、Camille Georges Wermuth

  DOI：10.1021/jm00100a015

  日期：1992.10

  Ten analogs of muscimol and thiomuscimol in which the amino function was delocalized in an amidinic system were prepared by N2 alkylation of 6-aryl-3-aminopyridazines with (chloromethyl)isoxazole or (chloromethyl)isothiazole derivatives. These muscimol and thiomuscimol derivatives show potent binding properties for GABA-A receptors (they displace [3H]GABA and [3H]gabazine) and provoke convulsions after

  通过将6-芳基-3-氨基哒嗪与（氯甲基）异恶唑或（氯甲基）异噻唑衍生物进行N 2烷基化反应，制备了氨基官能团在local胺基体系中离域的十种麝香酚和硫代麝香酚类似物。这些muscimol和thiomuscimol衍生物显示出对GABA-A受体的强效结合特性（它们取代了[3H] GABA和[3H] gabazine）并在静脉注射后引起惊厥。它们与我们小组提出的GABA-A拮抗剂模型药效基团非常吻合，并显示出与哒嗪基-GABA相似的结构活性图谱。