2-(4-ethoxycarbonylpiperazin-1-yl)-N'-(phthalazin-1-yl)acetohydrazide | 1375502-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(4-ethoxycarbonylpiperazin-1-yl)-N'-(phthalazin-1-yl)acetohydrazide
• 英文别名: Ethyl 4-[2-oxo-2-(2-phthalazin-1-ylhydrazinyl)ethyl]piperazine-1-carboxylate
• CAS: 1375502-55-8
• 化学式: C₁₇H₂₂N₆O₃
• 分子量: 358.4
• InChiKey: APATVTNQONSWOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  99.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(2H)-酞嗪酮 在 一水合肼 、 三乙胺 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.03h， 生成 2-(4-ethoxycarbonylpiperazin-1-yl)-N'-(phthalazin-1-yl)acetohydrazide
  参考文献：
  名称：

  Synthesis, vasorelaxant activity, and molecular modeling study of some new phthalazine derivatives

  摘要：

  New phthalazine-based vasodilators were synthesized through the chloroacylation of the starting compound 1-hydrazinophthalazine 4 to give the two key intermediates 5 and 7. These intermediates were used to alkylate various cyclic amines to furnish the final compounds 6a-h and 8a-h. Compounds were tested for their vasorelaxant activities against nor-adrenaline-induced spasm on thoracic rat aorta rings and compared to the reference drug, prazosin. Seven compounds showed higher activity than prazosin, especially compound 8d having an IC50 = 0.10 mM. Molecular modeling studies, including fitting of the synthesized compounds to a 3D-pharmacophore and their docking into optimized homology model as alpha(1)-AR antagonists showed high docking score and fit values. Most vasodilation activities of tested compounds are consistent with their molecular modeling results. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.051

文献信息

• Synthesis, vasorelaxant activity, and molecular modeling study of some new phthalazine derivatives
  作者：Fadi M. Awadallah、Wafaa I. El-Eraky、Dalia O. Saleh

  DOI：10.1016/j.ejmech.2012.02.051

  日期：2012.6

  New phthalazine-based vasodilators were synthesized through the chloroacylation of the starting compound 1-hydrazinophthalazine 4 to give the two key intermediates 5 and 7. These intermediates were used to alkylate various cyclic amines to furnish the final compounds 6a-h and 8a-h. Compounds were tested for their vasorelaxant activities against nor-adrenaline-induced spasm on thoracic rat aorta rings and compared to the reference drug, prazosin. Seven compounds showed higher activity than prazosin, especially compound 8d having an IC50 = 0.10 mM. Molecular modeling studies, including fitting of the synthesized compounds to a 3D-pharmacophore and their docking into optimized homology model as alpha(1)-AR antagonists showed high docking score and fit values. Most vasodilation activities of tested compounds are consistent with their molecular modeling results. (C) 2012 Elsevier Masson SAS. All rights reserved.