N,N-dimethylguanidine nitrate | 70940-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: N,N-dimethylguanidine nitrate
• 英文别名: N,N'-Dimethyl-guanidin; Nitrat
• CAS: 70940-09-9
• 化学式: C₃H₉N₃*HNO₃
• 分子量: 150.137
• InChiKey: XDXUPUAATIQDJB-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  N,N-dimethylguanidine nitrate 、 (E)-3-(dimethylamino)-1-(2,4-dimethylthiazol-5-yl)prop-2-en-1-one 在 sodium hydroxide 作用下， 以 乙二醇甲醚 为溶剂， 反应 22.0h， 以57%的产率得到4-(2,4-dimethyl-1,3-thiazol-5-yl)-N,N-dimethylpyrimidin-2-amine
  参考文献：
  名称：

  2-Anilino-4-(thiazol-5-yl)pyrimidine CDK Inhibitors:  Synthesis, SAR Analysis, X-ray Crystallography, and Biological Activity

  摘要：

  Following the identification through virtual screening of 4-(2,4-dimethyl-thiazol-5-yl)pyrimidin-2-ylamines as moderately potent inhibitors of cyclin-dependent kinase-2 (CDK2), a CDK inhibitor analogue program was initiated. The first aims were to optimize potency and to evaluate the cellular mode of action of lead candidate molecules. Here the synthetic chemistry, the structure-guided design approach, and the structure-activity relationships (SARs) that led to the discovery of 2-anilino-4-(thiazol-5-yl)pyrimidine ATP-antagonistic CDK2 inhibitors, many with very low nM K(i)s against CDK2, are reported. Furthermore, X-ray crystal structures of four representative analogues from our chemical series in complex with CDK2 are presented, and these structures are used to rationalize the observed biochemical SARs. Finally results are reported that show, using the most potent CDK2 inhibitor compound from the current series, that the observed antiproliferative and proapoptotic effects are consistent with cellular CDK2 and CDK9 inhibition.

  DOI：

  10.1021/jm0309957