6-bromo-8-methyl-2-(phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one | 851756-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 6-bromo-8-methyl-2-(phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one
• 英文别名: 2-anilino-6-bromo-8-methylpyrido[2,3-d]pyrimidin-7-one
• CAS: 851756-49-5
• 化学式: C₁₄H₁₁BrN₄O
• 分子量: 331.172
• InChiKey: NKICMUUPNWIXEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  489.4±55.0 °C(Predicted)
• 密度：
  1.639±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-bromo-8-methyl-2-(phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one 在 四(三苯基膦)钯 、 三苯胂 、 三溴化硼 、 cesium fluoride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 6-(2-Hydroxy-6-methoxy-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：

  6-bromo-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one 在 间氯过氧苯甲酸 作用下， 生成 6-bromo-8-methyl-2-(phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-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

• PYRIDONS AS PDK1 INHIBITORS
  申请人：Engelhardt Harald

  公开号：US20110269958A1

  公开（公告）日：2011-11-03

  The present invention encompasses compounds of general formula (1) while the groups R 4 to R 7 and the units W, L, Q a and Q H are defined as in claim 1 , which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and their use as medicaments having the above-mentioned properties.

  本发明涵盖了一般式（1）的化合物，其中R4到R7和单位W、L、Qa和QH的定义如权利要求1所述，适用于治疗由过度或异常细胞增殖特征的疾病，并且它们作为具有上述特性的药物的用途。
• HETEROCYCLYL CARBONIC ACID AMIDES AS ANTIPROLIFERATIVE AGENTS, PDKL INHIBITORS
  申请人：Engelhardt Harald

  公开号：US20110313156A1

  公开（公告）日：2011-12-22

  The present invention encompasses compounds of general formula (1) wherein the units W, A, L, Q a and Q H are defined as in claim 1 , which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and their use as medicaments having the above-mentioned properties.

  本发明涵盖了一般式（1）中的化合物，其中W，A，L，Qa和QH的定义如权利要求书中所述，适用于治疗由过度或异常细胞增殖所特征化的疾病，并且它们作为具有上述特性的药物的用途。
• US8637549B2
  申请人：——

  公开号：US8637549B2

  公开（公告）日：2014-01-28
• [EN] NEW CHEMICAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS CHIMIQUES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2010007114A2

  公开（公告）日：2010-01-21

  The present invention encompasses compounds of general formula (1) wherein the units W, A, L, Qa and QH are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and their use as medicaments having the above-mentioned properties.
• 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.