4,5-Dihydro-6-(α-styryl)pyridazin-3(2H)-one | 35990-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,5-Dihydro-6-(α-styryl)pyridazin-3(2H)-one
• 英文别名: 4,5-Dihydro-6-α-styrylpyridazin-3(2H)-on；6-styryl-4,5-dihydro-2H-pyridazin-3-one；3(2H)-Pyridazinone, 4,5-dihydro-6-(2-phenylethenyl)-；3-(2-phenylethenyl)-4,5-dihydro-1H-pyridazin-6-one
• CAS: 35990-92-2
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: BHAMKLMGLDPCFV-UHFFFAOYSA-N

物化性质

• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-Dihydro-6-(α-styryl)pyridazin-3(2H)-one 在 氢氧化钾 、 selenium(IV) oxide 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 4-Benzyl-6-((E)-styryl)-2H-pyridazin-3-one
  参考文献：
  名称：

  Ismail, M. Fekry; Shams, Nabil A.; Mostafa, Omnia E., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 4, p. 371 - 372

  摘要：

  DOI：
• 作为产物：
  描述：

  δ-benzylidene levulinic acid 在 一水合肼 、 溶剂黄146 作用下， 生成 4,5-Dihydro-6-(α-styryl)pyridazin-3(2H)-one
  参考文献：
  名称：

  Structure-based molecular design, synthesis, and in vivo anti-inflammatory activity of pyridazinone derivatives as nonclassic COX-2 inhibitors

  摘要：

  A scaffold with bicyclic core carrying pyridazinone moiety, which exhibited potent in vivo anti-inflammatory activities, was introduced in this article. The design of these compounds was assisted by docking and superposition experiments on cyclooxygenase-2 enzyme. The activity of a chloro analogue was as high as that of diclofenac in carrageenan-induced rat paw edema anti-inflammatory screening.

  DOI：

  10.1007/s00044-009-9218-4

文献信息

• Synthesis and anti-inflammatory activity of novel pyridazine and pyridazinone derivatives as non-ulcerogenic agents
  作者：Makarem M. Saeed、Nadia A. Khalil、Eman M. Ahmed、Kholoud I. Eissa

  DOI：10.1007/s12272-012-1205-5

  日期：2012.12

  Herein, we report the synthesis and pharmacological properties of several series of pyridazine and pyridazinone derivatives. All the synthesized compounds were tested, in vivo, for their anti-inflammatory and ulcerogenic properties against indomethacin, as a reference compound. Compounds 4a and 9d have shown a potent anti-inflammatory activity more than indomethacin with rapid onset of action and safe gastric profile. The latter compounds were then selected for further investigation. In the MTT assay in vitro, both compounds were identified as potent and selective COX-2 inhibitors.

  在此，我们报告了几系列吡嗪和吡嗪酮衍生物的合成和药理性质。所有合成的化合物都进行了体内测试，以评估其抗炎和溃疡形成特性，参考化合物为吲哚美辛。化合物4a和9d显示出比吲哚美辛更强的抗炎活性，且起效迅速，胃部安全性良好。这些化合物随后被选择进行进一步研究。在体外的MTT实验中，这两种化合物被确定为有效且选择性的COX-2抑制剂。