6-(2,6-Dimethoxy-phenyl)-8-methyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one | 851756-70-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(2,6-Dimethoxy-phenyl)-8-methyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one
• 英文别名: 2-anilino-6-(2,6-dimethoxyphenyl)-8-methylpyrido[2,3-d]pyrimidin-7-one
• CAS: 851756-70-2
• 化学式: C₂₂H₂₀N₄O₃
• 分子量: 388.426
• InChiKey: JRPLMLPNEXPGSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(2,6-Dimethoxy-phenyl)-8-methyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 6-(2,6-Dihydroxy-phenyl)-8-methyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one
  参考文献：
  名称：

  Structure–activity relationships for 2-anilino-6-phenylpyrido[2,3-d]pyrimidin-7(8H)-ones as inhibitors of the cellular checkpoint kinase Wee1

  摘要：

  A series of 2-anilino-6-phenylpyrido[2,3-d]-alpyrimidin-7(8H)-ones were synthesized and evaluated for their inhibitory properties against the non-receptor kinase c-Src and the G2/M checkpoint kinase Weel. Overall, the compounds were 10-100-fold more potent inhibitors of c-Src than Weel, and variation of substituents on the 6-phenyl ring did not markedly alter this preference. Solubilizing substituents off the 2-anilino ring in many cases increased Wee I activity, thus lowering this preference to about 10-fold. 5-Alkyl substituted analogs were generally Weel selective, but at the expense of absolute potency. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.079
• 作为产物：
  描述：

  2-(甲基硫代)吡啶并[2,3-d]嘧啶-7(8h)-酮 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 三苯胂 、 caesium carbonate 、 间氯过氧苯甲酸 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-(2,6-Dimethoxy-phenyl)-8-methyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one
  参考文献：
  名称：

  Structure–activity relationships for 2-anilino-6-phenylpyrido[2,3-d]pyrimidin-7(8H)-ones as inhibitors of the cellular checkpoint kinase Wee1

  摘要：

  A series of 2-anilino-6-phenylpyrido[2,3-d]-alpyrimidin-7(8H)-ones were synthesized and evaluated for their inhibitory properties against the non-receptor kinase c-Src and the G2/M checkpoint kinase Weel. Overall, the compounds were 10-100-fold more potent inhibitors of c-Src than Weel, and variation of substituents on the 6-phenyl ring did not markedly alter this preference. Solubilizing substituents off the 2-anilino ring in many cases increased Wee I activity, thus lowering this preference to about 10-fold. 5-Alkyl substituted analogs were generally Weel selective, but at the expense of absolute potency. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.079

文献信息

• Structure–activity relationships for 2-anilino-6-phenylpyrido[2,3-d]pyrimidin-7(8H)-ones as inhibitors of the cellular checkpoint kinase Wee1
  作者：Brian D. Palmer、Jeff B. Smaill、Gordon W. Rewcastle、Ellen M. Dobrusin、Alan Kraker、Charles W. Moore、Randall W. Steinkampf、William A. Denny

  DOI：10.1016/j.bmcl.2005.01.079

  日期：2005.4

  A series of 2-anilino-6-phenylpyrido[2,3-d]-alpyrimidin-7(8H)-ones were synthesized and evaluated for their inhibitory properties against the non-receptor kinase c-Src and the G2/M checkpoint kinase Weel. Overall, the compounds were 10-100-fold more potent inhibitors of c-Src than Weel, and variation of substituents on the 6-phenyl ring did not markedly alter this preference. Solubilizing substituents off the 2-anilino ring in many cases increased Wee I activity, thus lowering this preference to about 10-fold. 5-Alkyl substituted analogs were generally Weel selective, but at the expense of absolute potency. (c) 2005 Elsevier Ltd. All rights reserved.