2-[(6-oxo-3-phenyl-1H-pyridazin-4-yl)methylidene]propanedioic acid | 1001620-53-6

• 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: 2-[(6-oxo-3-phenyl-1H-pyridazin-4-yl)methylidene]propanedioic acid
• CAS: 1001620-53-6
• 化学式: C₁₄H₁₀N₂O₅
• 分子量: 286.244
• InChiKey: PPGJTMZDPMTXDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  dimethyl 2-[(6-oxo-3-phenyl-1H-pyridazin-4-yl)methylidene]propanedioate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以60%的产率得到2-[(6-oxo-3-phenyl-1H-pyridazin-4-yl)methylidene]propanedioic acid
  参考文献：
  名称：

  Design, Synthesis, and Structure–Activity Relationships of a Novel Series of 5-Alkylidenepyridazin-3(2H)-ones with a Non-cAMP-Based Antiplatelet Activity

  摘要：

  5-Alkylidenepyridazin-3-ones with four points of diversity (R-2, R-6, X, Y) have been synthesized and evaluated as platelet aggregation inhibitors. Several derivatives eliciting antiplatelet activity in the low micromolar range (e.g., 14e, 14k, 14p, 14v, IC50 congruent to 1 mu M) were identified. Structure-activity relationships studies on these compounds revealed the key molecular determinants of this new family of antiplatelet agents: (a) two ester groups in the alkoxy moieties; (b) lipophilic substituents at the N2 position of the pyridazin-3-one. The preliminary results of a pharmacological study aimed at determining the mechanism of action of a set of representative compounds revealed that, unlike other pyridazinones, the documented antiplatelet effect is not a consequence of a PDE-III inhibitory activity.

  DOI：

  10.1021/jm061401d

文献信息

• Design, Synthesis, and Structure–Activity Relationships of a Novel Series of 5-Alkylidenepyridazin-3(2<i>H</i>)-ones with a Non-cAMP-Based Antiplatelet Activity
  作者：Alberto Coelho、Enrique Raviña、Nuria Fraiz、Matilde Yáñez、Reyes Laguna、Ernesto Cano、Eddy Sotelo

  DOI：10.1021/jm061401d

  日期：2007.12.27

  5-Alkylidenepyridazin-3-ones with four points of diversity (R-2, R-6, X, Y) have been synthesized and evaluated as platelet aggregation inhibitors. Several derivatives eliciting antiplatelet activity in the low micromolar range (e.g., 14e, 14k, 14p, 14v, IC50 congruent to 1 mu M) were identified. Structure-activity relationships studies on these compounds revealed the key molecular determinants of this new family of antiplatelet agents: (a) two ester groups in the alkoxy moieties; (b) lipophilic substituents at the N2 position of the pyridazin-3-one. The preliminary results of a pharmacological study aimed at determining the mechanism of action of a set of representative compounds revealed that, unlike other pyridazinones, the documented antiplatelet effect is not a consequence of a PDE-III inhibitory activity.