2-(甲氧基甲基)-6-苯基-5-(2-苯基乙烯基)哒嗪-3-酮 | 404936-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-(甲氧基甲基)-6-苯基-5-(2-苯基乙烯基)哒嗪-3-酮
• 英文名称: 2-methoxymethyl-6-phenyl-5-styrylpyridazin-3(2H)-one
• 英文别名: 2-(Methoxymethyl)-6-phenyl-5-(2-phenylethenyl)pyridazin-3(2H)-one；2-(methoxymethyl)-6-phenyl-5-(2-phenylethenyl)pyridazin-3-one
• CAS: 404936-86-3
• 化学式: C₂₀H₁₈N₂O₂
• 分子量: 318.375
• InChiKey: FJDIUPMXBJKJEN-UHFFFAOYSA-N

物化性质

• 沸点：
  472.7±55.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(甲氧基甲基)-6-苯基-5-(2-苯基乙烯基)哒嗪-3-酮 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到6-phenyl-5-styrylpyridazin-3(2H)-one
  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
• 作为产物：
  描述：

  5-溴-6-苯基-3(2H)-吡嗪酮 在 palladium diacetate 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 2-(甲氧基甲基)-6-苯基-5-(2-苯基乙烯基)哒嗪-3-酮
  参考文献：
  名称：

  Pyridazines. Part 25: Efficient and selective deprotection of pharmacologically useful 2-MOM-pyridazinones using Lewis acids

  摘要：

  An efficient and selective procedure for the cleavage of a methoxymethyl group at the 2-position in acid-sensitive pyridazinones is presented. Deprotection with Lewis acids (boron tribromide or aluminium chloride) affords 3(2H)-pyridazinones under mild conditions without affecting multiple bonds in substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01898-6

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.
• Pyridazines. Part 25: Efficient and selective deprotection of pharmacologically useful 2-MOM-pyridazinones using Lewis acids
  作者：Eddy Sotelo、Alberto Coelho、Enrique Raviña

  DOI：10.1016/s0040-4039(01)01898-6

  日期：2001.12

  An efficient and selective procedure for the cleavage of a methoxymethyl group at the 2-position in acid-sensitive pyridazinones is presented. Deprotection with Lewis acids (boron tribromide or aluminium chloride) affords 3(2H)-pyridazinones under mild conditions without affecting multiple bonds in substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.