6-bromo-3-chloropyrazin-2-one | 1410166-55-0

• 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: 6-bromo-3-chloropyrazin-2-one
• 英文别名: 6-Bromo-3-chloropyrazin-2(1H)-one；6-bromo-3-chloro-1H-pyrazin-2-one
• CAS: 1410166-55-0
• 化学式: C₄H₂BrClN₂O
• 分子量: 209.43
• InChiKey: OFGJYDSIMLXEAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吗啉 、 6-bromo-3-chloropyrazin-2-one 在 N,N-二异丙基乙胺 作用下， 以 正丁醇 为溶剂， 反应 1.0h， 以45%的产率得到6-bromo-3-(morpholino)-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：

  3-(benzyloxy)-5-bromo-2-chloropyrazine 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以68%的产率得到6-bromo-3-chloropyrazin-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

• PYRIDIN-2(1H)-ONE QUINOLINONE DERIVATIVES AS MUTANT-ISOCITRATE DEHYDROGENASE INHIBITORS
  申请人：Forma Therapeutics, Inc.

  公开号：US20160083366A1

  公开（公告）日：2016-03-24

  The invention relates to inhibitors of mutant isocitrate dehydrogenase (mt-IDH) proteins with neomorphic activity useful in the treatment of cell-proliferation disorders and cancers, having the Formula: where A, U, W 1 , W 2 , W 3 , R 1 -R 6 , and R 9 are described herein.

  本发明涉及对突变异构己二酸脱氢酶（mt-IDH）蛋白的抑制剂，具有新型活性，可用于治疗细胞增殖障碍和癌症，其化学式为：其中A、U、W1、W2、W3、R1-R6和R9如本文所述。
• CN115850240
  申请人：——

  公开号：——

  公开（公告）日：——
• Design and synthesis of 2(1H)-pyrazinones as inhibitors of protein kinases
  作者：John J. Caldwell、Nicolas Veillard、Ian Collins

  DOI：10.1016/j.tet.2012.09.039

  日期：2012.11

  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.