5-bromo-3-(N-methylpiperazin-1-yl)-1H-pyrazin-2-one | 1410166-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5-bromo-3-(N-methylpiperazin-1-yl)-1H-pyrazin-2-one
• 英文别名: 5-bromo-3-(4-methylpiperazin-1-yl)-1H-pyrazin-2-one
• CAS: 1410166-27-6
• 化学式: C₉H₁₃BrN₄O
• 分子量: 273.132
• InChiKey: VKHRDBHQVSOUNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-3-(N-methylpiperazin-1-yl)-1H-pyrazin-2-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.33h， 以38%的产率得到5-(4-methoxyphenyl)-3-(4-methylpiperazin-1-yl)-1H-pyrazin-2-one
  参考文献：
  名称：

  Design and synthesis of 2(1H)-pyrazinones as inhibitors of protein kinases

  摘要：

  Kinase enzymes play a key role in the development and progression of cancer. Inhibitors of deregulated kinases are effective small molecule anticancer drugs. The 2(1H)-pyrazinone heterocycle is a previously unexploited motif that can fulfil the structural requirements for ATP-competitive inhibition of kinases. Rapid solution-phase syntheses of novel 3,5- and 3,6-disubstituted-2(1H)-pyrazinones were developed through selective, sequential substitution of 2,5-dihalo-3-benzyloxypyrazine and 3,5-dihalo-2(1H)-pyrazinone intermediates. Palladium-catalysed cross-couplings and SNAr reactions were used to introduce substituents chosen on the basis of the calculated physicochemical properties of the target pyrazinones. Representative compounds demonstrated good solubility, kinase inhibitory activity and antiproliferative activity in human tumour cells, confirming the suitability of this chemical class as a kinase-focused library. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.039
• 作为产物：
  描述：

  N-甲基哌嗪 、 2-羟基-3-氯-5-溴吡嗪 在 N,N-二异丙基乙胺 作用下， 以 正丁醇 为溶剂， 反应 1.0h， 以53%的产率得到5-bromo-3-(N-methylpiperazin-1-yl)-1H-pyrazin-2-one
  参考文献：
  名称：

  Design and synthesis of 2(1H)-pyrazinones as inhibitors of protein kinases

  摘要：

  Kinase enzymes play a key role in the development and progression of cancer. Inhibitors of deregulated kinases are effective small molecule anticancer drugs. The 2(1H)-pyrazinone heterocycle is a previously unexploited motif that can fulfil the structural requirements for ATP-competitive inhibition of kinases. Rapid solution-phase syntheses of novel 3,5- and 3,6-disubstituted-2(1H)-pyrazinones were developed through selective, sequential substitution of 2,5-dihalo-3-benzyloxypyrazine and 3,5-dihalo-2(1H)-pyrazinone intermediates. Palladium-catalysed cross-couplings and SNAr reactions were used to introduce substituents chosen on the basis of the calculated physicochemical properties of the target pyrazinones. Representative compounds demonstrated good solubility, kinase inhibitory activity and antiproliferative activity in human tumour cells, confirming the suitability of this chemical class as a kinase-focused library. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.039

文献信息

• KDM1A INHIBITORS FOR THE TREATMENT OF DISEASE
  申请人：Imago Biosciences Inc.

  公开号：EP3790867A1

  公开（公告）日：2021-03-17
• [EN] KDM1A INHIBITORS FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS DE KDM1A POUR LE TRAITEMENT D'UNE MALADIE
  申请人：IMAGO BIOSCIENCES INC

  公开号：WO2019217972A1

  公开（公告）日：2019-11-14

  The present disclosure relates to compounds and methods which may be useful as inhibitors of KDM1 A for the treatment or prevention of diseases. Methods of inhibition of KDM1 A, methods of increasing gamma globin gene expression, and methods to induce differentiation in cancer cells in a human or animal subject are also provided for treatment of disease such as acute myelogenous leukemia.