N-benzyl-4-chlorophthalazin-1-amine | 677322-97-3

• 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: N-benzyl-4-chlorophthalazin-1-amine
• CAS: 677322-97-3
• 化学式: C₁₅H₁₂ClN₃
• 分子量: 269.733
• InChiKey: SPVAQTODVZCKSM-UHFFFAOYSA-N

物化性质

• 沸点：
  500.0±35.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-4-chlorophthalazin-1-amine 在 sodium acetate trihydrate 、 溶剂黄146 作用下， 以65%的产率得到4-benzylamino-2H-phthalazin-1-one
  参考文献：
  名称：

  Design, synthesis, and molecular modelling of pyridazinone and phthalazinone derivatives as protein kinases inhibitors

  摘要：

  The design and synthesis of pyridazinone and phthalazinone derivatives are described. Newly synthesized compounds were tested on a panel of four kinases in order to evaluate their activity and potential selectivity. In addition, the promising compounds were tested on four cancer cell lines to examine cytotoxic effects. The compounds inhibited DYRK1A and GSK3 with different activity. SAR analysis and docking calculations were carried out to aid in the interpretation of the results. Taken together, our findings suggest that pyridazinone and phthalazinone scaffolds are interesting starting points for design of potent GSK3 and DYRK1A inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.027
• 作为产物：
  描述：

  邻苯二甲酰肼 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 N-benzyl-4-chlorophthalazin-1-amine
  参考文献：
  名称：

  N-苄基-4-苯基酞嗪-1-胺衍生物和制备方法、治疗RECQL4特异性表达的药物

  摘要：

  本发明属于有机化合物技术领域，具体涉及N‑苄基‑4‑苯基酞嗪‑1‑胺衍生物和制备方法、治疗RECQL4特异性表达的肝癌药物。本发明提供了一种N‑苄基‑4‑苯基酞嗪‑1‑胺衍生物，具有式I所示结构式，式I中R1为‑H或‑OCH3；R2为‑H、苯基、取代苯基、烷基、烷氧基、烯基或二苯氨基；R3为‑H、硝基或甲基；R4为‑H或苯基；R1、R2、R3和R4不同时为‑H。本发明提供的N‑苄基‑4‑苯基酞嗪‑1‑胺衍生物对RECQL4高表达的肝癌细胞SNU‑398的增殖具有较强的抑制作用。本发明为开发新的抗RECQL4高表达肝癌药物，以及临床个性化治疗RECQL4高表达的肝癌提供了科学实验数据；

  公开号：

  CN114014814B

文献信息

• N-苄基-4-苯基酞嗪-1-胺衍生物和制备方法、治疗RECQL4特异性表达的药物
  申请人：山东第一医科大学（山东省医学科学院）

  公开号：CN114014814B

  公开（公告）日：2023-07-25

  本发明属于有机化合物技术领域，具体涉及N‑苄基‑4‑苯基酞嗪‑1‑胺衍生物和制备方法、治疗RECQL4特异性表达的肝癌药物。本发明提供了一种N‑苄基‑4‑苯基酞嗪‑1‑胺衍生物，具有式I所示结构式，式I中R1为‑H或‑OCH3；R2为‑H、苯基、取代苯基、烷基、烷氧基、烯基或二苯氨基；R3为‑H、硝基或甲基；R4为‑H或苯基；R1、R2、R3和R4不同时为‑H。本发明提供的N‑苄基‑4‑苯基酞嗪‑1‑胺衍生物对RECQL4高表达的肝癌细胞SNU‑398的增殖具有较强的抑制作用。本发明为开发新的抗RECQL4高表达肝癌药物，以及临床个性化治疗RECQL4高表达的肝癌提供了科学实验数据；
• Design and synthesis of 3-aminophthalazine derivatives and structural analogues as PDE5 inhibitors: anti-allodynic effect against neuropathic pain in a mouse model
  作者：Maud Bollenbach、Claire Lugnier、Mélanie Kremer、Eric Salvat、Salim Megat、Frédéric Bihel、Jean-Jacques Bourguignon、Michel Barrot、Martine Schmitt

  DOI：10.1016/j.ejmech.2019.05.026

  日期：2019.9

  Neuropathic pain is a chronic pain caused by a lesion or disease affecting the somatosensory nervous system. To date, no specific treatment has been developed to cure this pain. Antidepressants and anticonvulsant drugs are used, but they do not demonstrate universal efficacy, and they often cause detrimental adverse effects. Some studies highlighted the efficacy of sildenafil, a well-known inhibitor of phosphodiesterase 5 (PDE5, (IC50=3.3 nM)), in models of pain. Based on these results, we focused our attention on MY 5445, another known PDE5 inhibitor. Homologues, isosteres and structural analogues of MY 5445 were designed and all synthesized compounds were evaluated for their inhibitory activity toward PDE5. Selectivity profiles towards other PDE1-4 isoenzymes, water solubility and stability in acidic medium of the most potent PDE5 inhibitors were determined and the aminophthalazine 16h and its mimetic 41n (3-aminoindazole) were evaluated in comparison to MY 5445 (4b) in vivo in a model of neuropathic pain induced by sciatic nerve cuffing in mice (3 and 0.5 mg/kg, ip twice a day). Both compounds showed the same efficacy on neuropathic allodynia as MY 5445, and thus produced a significant relief of mechanical hypersensitivity after 12 days of treatment. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Design, synthesis, and molecular modelling of pyridazinone and phthalazinone derivatives as protein kinases inhibitors
  作者：Mohamed Elagawany、Mohamed A. Ibrahim、Hany Emary Ali Ahmed、A.Sh. El-Etrawy、Adel Ghiaty、Zakaria K. Abdel-Samii、Said A. El-Feky、Jürgen Bajorath

  DOI：10.1016/j.bmcl.2013.02.027

  日期：2013.4

  The design and synthesis of pyridazinone and phthalazinone derivatives are described. Newly synthesized compounds were tested on a panel of four kinases in order to evaluate their activity and potential selectivity. In addition, the promising compounds were tested on four cancer cell lines to examine cytotoxic effects. The compounds inhibited DYRK1A and GSK3 with different activity. SAR analysis and docking calculations were carried out to aid in the interpretation of the results. Taken together, our findings suggest that pyridazinone and phthalazinone scaffolds are interesting starting points for design of potent GSK3 and DYRK1A inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.