1-苄基-6-氧代-1,6-二氢哒嗪-4-甲醛 | 1001620-76-3

• 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: 1-苄基-6-氧代-1,6-二氢哒嗪-4-甲醛
• 英文名称: 1-benzyl-6-oxo-1,6-dihydropyridazine-4-carbaldehyde
• 英文别名: 1-Benzyl-6-oxopyridazine-4-carbaldehyde
• CAS: 1001620-76-3
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: PSAICHYPKXOZDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-乙酰基呋喃 、 1-苄基-6-氧代-1,6-二氢哒嗪-4-甲醛 在 silica-supported aluminum chloride 作用下， 以 乙醇 为溶剂， 以52%的产率得到2-benzyl-5-[3-(furan-2-yl)-3-oxoprop-1-enyl]pyridazin-3-one
  参考文献：
  名称：

  Silica-Supported Aluminum Chloride-Assisted Solution Phase Synthesis of Pyridazinone-Based Antiplatelet Agents

  摘要：

  A solution phase protocol that enabled the synthesis of three diverse libraries of pyridazin-3-ones incorporating alpha,beta-unsaturated moieties at position S of the heterocyclic core has been developed using silica-supported aluminum trichloride as a heterogeneous and reusable catalyst. This robust procedure has facilitated the hit to lead process for these series of compounds and allowed the identification of new potent derivatives that elicit antiplatelet activity in the low micromolar range.

  DOI：

  10.1021/co100017h
• 作为产物：
  描述：

  2-benzyl-5-vinylpyridazin-3(2H)-one 在 氧气 、 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 以67%的产率得到1-苄基-6-氧代-1,6-二氢哒嗪-4-甲醛
  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