4-pyrrolidino-1-(2H)-phthalazinone | 78755-14-3

• 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: 4-pyrrolidino-1-(2H)-phthalazinone
• 英文别名: 4-pyrrolidino-1(2H)-phthalazinone；4-pyrrolidin-1-yl-2H-phthalazin-1-one
• CAS: 78755-14-3
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: SKRSSEJVRFBVBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-pyrrolidino-1-(2H)-phthalazinone 在 sodium hydride 、 sodium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-{3-[4-(3-acetamidophenyl)piperidin-1-yl]propyl}-4-(pyrrolidin-1-yl)phthalazin-1(2H)-one
  参考文献：
  名称：

  4-Aminophthalazin-1(2H)-one Derivatives as Melanin Concentrating Hormone Receptor 1 (MCH-R1) Antagonists

  摘要：

  DOI：

  10.5012/bkcs.2013.34.12.3851
• 作为产物：
  描述：

  4-(4-bromobutylamino)-2H-phthalazin-1-one 生成 4-pyrrolidino-1-(2H)-phthalazinone
  参考文献：
  名称：

  KOERMENDY, K.;RUFF, F., ACTA CHIM. HUNG., 1983, 112, N 1, 65-81

  摘要：

  DOI：

文献信息

• Koermendy, K.; Ruff, F., Acta Chimica Academiae Scientiarum Hungaricae, 1981, vol. 106, # 2, p. 155 - 166
  作者：Koermendy, K.、Ruff, F.

  DOI：——

  日期：——
• 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.; Ruff, F., Acta Chimica Hungarica, 1983, vol. 112, # 1, p. 65 - 82
  作者：Koermendy, K.、Ruff, F.

  DOI：——

  日期：——
• KOERMENDY K.; RUFF F., ACTA CHIM. ACAD. SCI. HUNG., 1981, 106, NO 2, 155-166
  作者：KOERMENDY K.、 RUFF F.

  DOI：——

  日期：——