5-(2-hydroxyethylamino)pyrido<2,3-d>pyridazine-8(7H)-one | 81214-71-3

• 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: 5-(2-hydroxyethylamino)pyrido<2,3-d>pyridazine-8(7H)-one
• 英文别名: 5-(2-hydroxyethylamino)pyrido<2,3-d>pyridazin-8(7H)-one；5-(2-hydroxyethylamino)-7H-pyrido[2,3-d]pyridazin-8-one
• CAS: 81214-71-3
• 化学式: C₉H₁₀N₄O₂
• 分子量: 206.204
• InChiKey: VOWKEDBEVAVFDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.28
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  90.9
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(2-hydroxyethylamino)pyrido<2,3-d>pyridazine-8(7H)-one 在 氢氧化钾 、 ammonium hydroxide 、 氢溴酸 作用下， 以 水 为溶剂， 反应 2.5h， 生成 6-(2-ammoniumethyl)pyrido<2,3-d>pyridazin-5-one-8-olate
  参考文献：
  名称：

  Koermendy, Karoly; Soltesz, Zsuzsanna; Ruff, Ferenc, Acta Chimica Hungarica, 1985, vol. 120, # 3, p. 177 - 190

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-吡啶二羧酸酐 在 吡啶 、 盐酸 、 氢氧化钾 、 一水合肼 作用下， 以 氯仿 为溶剂， 反应 1.75h， 生成 5-(2-hydroxyethylamino)pyrido<2,3-d>pyridazine-8(7H)-one
  参考文献：
  名称：

  Kormendy, K.; Kovacs, T.; Szulagyi, J., Acta Chimica Academiae Scientiarum Hungaricae, 1981, vol. 108, # 2, p. 167 - 182

  摘要：

  DOI：

文献信息

• N -ferrocenylpyridazinones and new organic analogues: Synthesis, cyclic voltammetry, DFT analysis and in vitro antiproliferative activity associated with ROS-generation
  作者：Tamás Jernei、Szilvia Bősze、Rita Szabó、Ferenc Hudecz、Katalin Majrik、Antal Csámpai

  DOI：10.1016/j.tet.2017.09.015

  日期：2017.10

  Employing an optimized Pd-catalyzed cross-coupling reaction promoted by CuI, novel N-ferrocenylpyridazinones along with N-phenyl- and N-(2-pyridyl) analogues were synthesized from readily available heterocyclic precursors, iodoferrocene, iodobenzene and 2-bromopyridine. With exception of the ferrocenylation of 6-ferrocenylpyridazin-3(2H)-one yielding both N- and O-substituted products, the studied reactions exclusively afforded N-aryl lactams. The novel compounds exhibited cytotoxicity towards HEPG2 and HT-29 human malignant cells under in vitro conditions. The measured IC50 values supplemented with the results of cyclic voltammetry and DFT calculations suggest that the cytotoxic activity of the N- and O-ferrocenyl-substituted derivatives and the decreased effect of the N-phenyl analogues seem to be at least partly associated with the potential to generate reactive oxygen species (ROS). This interpretation, allowing the prediction of characteristic substituent-dependent SAR, was supported by the results of related studies on the practically inactive N-(2-pyridyl)pyridazinones assumed to be present in protonated chelate forms with highly a decreased propensity to undergo ionization. (C) 2017 Elsevier Ltd. All rights reserved.
• KOERMENDY, K.;KOVACS, T.;SZULAGYI, J.;FUFF, F.;KOEVESDI, I., ACTA CHIM. ACAD. SCI. HUNG., 1981, 108, N 2, 167-182
  作者：KOERMENDY, K.、KOVACS, T.、SZULAGYI, J.、FUFF, F.、KOEVESDI, I.

  DOI：——

  日期：——
• KOERMENDY, K.;SOLTESZ, Z.;RUFF, F.;KOEVESDI, I., ACTA CHIM. HUNG., 1985, 120, N 3, 177-190
  作者：KOERMENDY, K.、SOLTESZ, Z.、RUFF, F.、KOEVESDI, I.

  DOI：——

  日期：——