4-bromo-2-(4-nitrophenyl)phthalazin-1(2H)-one

• 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-bromo-2-(4-nitrophenyl)phthalazin-1(2H)-one
• 英文别名: 4-bromo-2-(4-nitro-phenyl)-2H-phthalazin-1-one；4-bromo-2-(4-nitrophenyl)phthalazin-1-one
• 化学式: C₁₄H₈BrN₃O₃
• 分子量: 346.14
• InChiKey: YDIDJQAXSBPLKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-bromo-2-(4-nitrophenyl)phthalazin-1(2H)-one 在 二氧化铂 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以to yield title compound (0.61 g, 67% yield)的产率得到2-(4-amino-phenyl)-4-bromo-2H-phthalazin-1-one
  参考文献：
  名称：

  Methods of inhibiting BTK and SYK protein kinases

  摘要：

  本文披露了一种抑制酪氨酸激酶的方法，其中所述的酪氨酸激酶是BTK或SYK，包括向需要治疗的患者施用公式I所述的化合物的治疗有效量。这些化合物可用于治疗自身免疫和炎症性疾病。

  公开号：

  US07501410B2
• 作为产物：
  描述：

  邻苯二甲酰肼 在 sodium hydride 、 溶剂黄146 、 三溴氧磷 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 4-bromo-2-(4-nitrophenyl)phthalazin-1(2H)-one
  参考文献：
  名称：

  The synthesis and anti‐tumour properties of novel 4-substituted phthalazinones as Aurora B kinase inhibitors

  摘要：

  A series of novel 4-substituted phthalazinones as Aurora B kinase inhibitors was synthesized and evaluated the anti-proliferative activities against A549, HCT116, MCF-7 and HepG2 cells. 1-(4-(2-((4-Oxo-3,4-dihydrophthalazin-1-yl)amino)ethyl) phenyl)-3-(3-(trifluoromethyl)phenyl)urea (17b) exhibited the most potent anti-proliferative activity against HCT116 cells with IC50 value of 4.35 ± 1.21 μM, as well as the moderate Aurora B inhibitory activity with the IC50 value of 142 nM. Furthermore, 17b inhibited the phosphorylation of Aurora B on Thr232, leading to cell cycle arrest in the G2/M phase by down-regulating the expression of CyclinB1 and Cdc2 proteins, and apoptosis by up-regulating the expression of BAD and Bax proteins in HCT116 cells. In addition, a docking study revealed that 17b could form key hydrogen bonds with Ala173, Glu171 and Glu177 in Aurora B. All the results reveal that 17b is worthy of further development as an Aurora B kinase inhibitor.

  DOI：

  10.1016/j.bmcl.2020.127556

文献信息

• [EN] NOVEL PHTHALAZINONE DERIVATIVES, AS AURORA-A KINASE INHIBITORS<br/>[FR] NOUVEAUX COMPOSÉS DE PHTALAZINONE SERVANT D'INHIBITEURS DE LA KINASE AURORA-A
  申请人：HOFFMANN LA ROCHE

  公开号：WO2006032518A1

  公开（公告）日：2006-03-30

  Objects of the present invention are the compounds of formula (I) their pharmaceutically acceptable salts, enantiomeric forms, diastereoisomers and racemates, the preparation of the above-mentioned compounds, medicaments containing them and their manufacture, as well as the use of the above-mentioned compounds in the control or prevention of illnesses such as cancer.

  本发明的对象是公式（I）的化合物及其药学上可接受的盐、对映体形式、二对映异构体和消旋体，上述化合物的制备，含有它们的药物以及其制造，以及上述化合物在控制或预防癌症等疾病中的应用。
• Phthalazinone derivatives
  申请人：Boyd Edward

  公开号：US20060089359A1

  公开（公告）日：2006-04-27

  Compounds of formula I their pharmaceutically acceptable salts, enantiomeric forms, diastereoisomers and racemates are disclosed. Also disclosed are methods for the preparation of the above-mentioned compounds, pharmaceutical compositions containing them, as well as the use of the above-mentioned compounds in the treatment, control or prevention of illnesses such as cancer.

  公开了式I的化合物及其药学上可接受的盐、对映体、二对映异构体和混合物。还公开了制备上述化合物的方法、含有它们的药物组合物，以及上述化合物在治疗、控制或预防癌症等疾病中的应用。
• NOVEL PHTHALAZINONE DERIVATIVES, AS AURORA-A KINASE INHIBITORS
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1794148A1

  公开（公告）日：2007-06-13
• METHODS OF INHIBITING BTK AND SYK PROTEIN KINASES
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1998777A1

  公开（公告）日：2008-12-10
• US7226923B2
  申请人：——

  公开号：US7226923B2

  公开（公告）日：2007-06-05