dibenzyl 2-[(6-oxo-3-phenyl-1H-pyridazin-4-yl)methylidene]propanedioate | 1001620-22-9

• 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: dibenzyl 2-[(6-oxo-3-phenyl-1H-pyridazin-4-yl)methylidene]propanedioate
• CAS: 1001620-22-9
• 化学式: C₂₈H₂₂N₂O₅
• 分子量: 466.493
• InChiKey: APMJSNAKRQNEKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二苄基马来酸酯 、 6-氧代-3-苯基-1H-哒嗪-4-甲醛 在 三氯化铝 作用下， 以 1,4-二氧六环 为溶剂， 以78%的产率得到dibenzyl 2-[(6-oxo-3-phenyl-1H-pyridazin-4-yl)methylidene]propanedioate
  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.