4-chloro-5-(piperazin-1-yl)-2,3-dihydropyridazin-3-one | 153276-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-chloro-5-(piperazin-1-yl)-2,3-dihydropyridazin-3-one
• 英文别名: 4-chloro-5-(piperazin-1-yl)pyridazin-3(2H)-one；4-chloro-5-piperazin-1-yl-pyridazin-3-one；4-(4-chloro-3-oxo-2H-pyridazin-5-yl)-piperazine；4-chloro-5-piperazin-4-ium-1-ylpyridazin-3-olate
• CAS: 153276-34-7
• 化学式: C₈H₁₁ClN₄O
• mdl: MFCD09040970
• 分子量: 214.655
• InChiKey: ICFYLQIKMKKTQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-5-(piperazin-1-yl)-2,3-dihydropyridazin-3-one 在 sodium hydroxide 、 sodium carbonate 作用下， 以 乙醇 、 异戊醇 为溶剂， 反应 6.0h， 生成 1,2 bis-<2-(4-chloro)-5-<4-(2-methoxyphenoxyethyl)-1-piperazinyl>-3(2H)-pyridazinonyl>ethane
  参考文献：
  名称：

  New pyridazinones: synthesis and correlation between structure and α-blocking activity

  摘要：

  The synthesis of a series of 5-(4-piperazinyl)-3(2H)-pyridazinone has been reported. The blocking activity of these compounds was determined on the pre- and postsynaptic alpha-adrenoreceptors of isolated rat vas deferens.

  DOI：

  10.1016/0223-5234(93)90097-x
• 作为产物：
  描述：

  4-chloro-5-(piperazin-1-yl)-2H-pyridazin-3-one hydrochloride 在 sodium hydroxide 作用下， 以 水 为溶剂， 以2.4 g的产率得到4-chloro-5-(piperazin-1-yl)-2,3-dihydropyridazin-3-one
  参考文献：
  名称：

  The Discovery of a Selective, Small Molecule Agonist for the Mas-Related Gene X1 Receptor

  摘要：

  The novel 7-transmembrane receptor MrgX1 is located predominantly in the dorsal root ganglion and has consequently been implicated in the perception of pain. Here we describe the discovery and optimization of a small molecule agonist and initial docking studies of this ligand into the receptor in order to provide a suitable lead and tool compound for the elucidation of the physiological function of the receptor.

  DOI：

  10.1021/jm800962k

文献信息

• Structure-Activity Relationships in a Series of 8-Substituted Xanthines as Bronchodilator and A1-Adenosine Receptor Antagonists
  作者：Stefano Corsano、Giovannella Strappaghetti、Rossana Scapicchi、Antonio Lucacchini、Generoso Senatore

  DOI：10.1002/ardp.19953280905

  日期：——

  Four new derivatives of 8‐piperazine ethyl xanthine were synthesized and their bronchospasmolytic activity and A1‐adenosine affinity were studied. Their relaxant action in the tracheal muscle was lower than that of theophylline and that of theophylline derivatives substituted at the 7‐position. Only compound 9, where the methyl group in the 1‐position of the theophylline was substituted by an isobutyl

  合成了 8-哌嗪乙基黄嘌呤的四种新衍生物，并研究了它们的支气管痉挛活性和 A1-腺苷亲和力。它们在气管肌肉中的松弛作用低于茶碱和 7 位取代的茶碱衍生物。只有化合物 9，其中茶碱 1 位的甲基被异丁基取代，对 A1-腺苷受体显示出良好的亲和力。
• Bronchodilator Activity of Theophylline Derivatives Substituted at the 7-Position
  作者：Stefano Corsano、Rossana Scapicchi、Giovannella Strappaghetti

  DOI：10.1002/ardp.19943271006

  日期：——

  Theophylline derivatives with several groups linked at the 7‐position were synthesized and their pharmacological activities were studied on guinea pig. Relaxant action in the tracheal muscle was increased in comparison with that of theophylline when the 3(2H)‐pyridazinone system was linked to 7‐(2‐ethyl)‐theophylline through the piperazine ring, but decreased when the 7‐(2‐ethyl)‐theophylline was linked

  合成了7-位连接多个基团的茶碱衍生物，并在豚鼠身上研究了它们的药理活性。当 3 (2H)-哒嗪酮系统通过哌嗪环与 7-(2-乙基)-茶碱相连时，与茶碱相比，气管肌肉的松弛作用增加，但当 7-(2-乙基)-茶碱与 7-(2-乙基)-茶碱相连时，气管肌肉的松弛作用减弱。 ) -茶碱通过氨基与 3 (2H) -哒嗪酮环相连。
• [EN] PYRIDAZINONES AND METHODS OF USE THEREOF<br/>[FR] PYRIDAZINONES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：GOLDFINCH BIO INC

  公开号：WO2019055966A3

  公开（公告）日：2019-04-18
• WO2008/146064
  申请人：——

  公开号：——

  公开（公告）日：——
• Adenosine receptors: synthesis, structure-activity relationships and biological activity of new 6-amino purine derivatives
  作者：Giovannella Strappaghetti、Stefano Corsano、Roberta Barbaro、Antonio Lucacchini、Gino Giannaccini、Laura Betti

  DOI：10.1016/s0223-5234(98)80050-0

  日期：1998.6

  The synthesis and evaluation of the biological activity of a series of pyridazin-3(2H)-one derivatives is reported. The compounds were tested in radioligand binding assays for affinity at A(1) and A(2A) adenosine receptors in bovine brain cortical membranes, and bovine brain striatal membranes, respectively. None of the compounds shows any affinity towards A(2A) receptor, while compounds in which the 6-chloro-pyridazin-3(2H)-one or 6-phenyl-pyridazin-3(2H)-one group is linked through a chain of two carbon atoms in the 6 position of the adenosine, show a good affinity towards A(1) adenosine receptor, particularly compound 8 in which a phenyl-pyridazinone group is present shows highest affinity with K-i values 6.6 nM. (C) Elsevier, Paris.