5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-methanesulfonyl-1H,2H,3H,4H-[1,3]diazino[4,5-d]pyrimidin-2-one | 906462-83-7

• 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: 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-methanesulfonyl-1H,2H,3H,4H-[1,3]diazino[4,5-d]pyrimidin-2-one
• 英文别名: 4-(2-chlorophenyl)-8-(2,6-dichlorophenyl)-2-methylsulfonyl-5,6-dihydropyrimido[4,5-d]pyrimidin-7-one
• CAS: 906462-83-7
• 化学式: C₁₉H₁₃Cl₃N₄O₃S
• 分子量: 483.762
• InChiKey: LDJYQPLHXNCUPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-methanesulfonyl-1H,2H,3H,4H-[1,3]diazino[4,5-d]pyrimidin-2-one 在 氨 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 7-amino-5-(2-chloro-phenyl)-1-(2,6-dichloro-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one
  参考文献：
  名称：

  p38 MAP kinase inhibitors. Part 3: SAR on 3,4-dihydropyrimido[4,5-d]pyrimidin-2-ones and 3,4-dihydropyrido[4,3-d]pyrimidin-2-ones

  摘要：

  p38 inhibitors based on 3,4-dihydropyrimido[4,5-d]pyrimidin-2-one and 3,4-dihydropyrido[4,3-d]pyrimidin-2-one platforms were synthesized and preliminary SAR explored. Among the pyrimido-pyrimidones the emergence of two sub-types of analogs-C7-amino-pyrimidines such as 24 and C7-amino-piperidines such as 42-characterized with good p38 inhibition and better off-target profiles in terms of ion channel activities was significant. Representative compound 54 in the pyrido-pyrimidone class was found to be equipotent with corresponding analog in the quinazolinone series. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.045
• 作为产物：
  描述：

  6-(2-chloro-phenyl)-2-mercapto-5-methyl-pyrimidin-4-ol 在 吡啶 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 potassium carbonate 、 三氟乙酸 、 三氯氧磷 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-methanesulfonyl-1H,2H,3H,4H-[1,3]diazino[4,5-d]pyrimidin-2-one
  参考文献：
  名称：

  p38 MAP kinase inhibitors. Part 3: SAR on 3,4-dihydropyrimido[4,5-d]pyrimidin-2-ones and 3,4-dihydropyrido[4,3-d]pyrimidin-2-ones

  摘要：

  p38 inhibitors based on 3,4-dihydropyrimido[4,5-d]pyrimidin-2-one and 3,4-dihydropyrido[4,3-d]pyrimidin-2-one platforms were synthesized and preliminary SAR explored. Among the pyrimido-pyrimidones the emergence of two sub-types of analogs-C7-amino-pyrimidines such as 24 and C7-amino-piperidines such as 42-characterized with good p38 inhibition and better off-target profiles in terms of ion channel activities was significant. Representative compound 54 in the pyrido-pyrimidone class was found to be equipotent with corresponding analog in the quinazolinone series. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.045

文献信息

• p38 MAP kinase inhibitors. Part 3: SAR on 3,4-dihydropyrimido[4,5-d]pyrimidin-2-ones and 3,4-dihydropyrido[4,3-d]pyrimidin-2-ones
  作者：Swaminathan R. Natarajan、David D. Wisnoski、James E. Thompson、Edward A. O’Neill、Stephen J. O’Keefe

  DOI：10.1016/j.bmcl.2006.05.045

  日期：2006.8

  p38 inhibitors based on 3,4-dihydropyrimido[4,5-d]pyrimidin-2-one and 3,4-dihydropyrido[4,3-d]pyrimidin-2-one platforms were synthesized and preliminary SAR explored. Among the pyrimido-pyrimidones the emergence of two sub-types of analogs-C7-amino-pyrimidines such as 24 and C7-amino-piperidines such as 42-characterized with good p38 inhibition and better off-target profiles in terms of ion channel activities was significant. Representative compound 54 in the pyrido-pyrimidone class was found to be equipotent with corresponding analog in the quinazolinone series. (c) 2006 Elsevier Ltd. All rights reserved.