2-anilino-4-(2,4-dimethylthiazol-5-yl)pyrimidine | 674333-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-anilino-4-(2,4-dimethylthiazol-5-yl)pyrimidine
• 英文别名: 4-(2,4-dimethyl-1,3-thiazol-5-yl)-N-phenylpyrimidine-2-amine；2-Pyrimidinamine, 4-(2,4-dimethyl-5-thiazolyl)-N-phenyl-；4-(2,4-dimethyl-1,3-thiazol-5-yl)-N-phenylpyrimidin-2-amine
• CAS: 674333-60-9
• 化学式: C₁₅H₁₄N₄S
• 分子量: 282.369
• InChiKey: CKJOPHUBYHDSMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-二甲基-5-乙酰基噻唑 在 sodium hydroxide 作用下， 以 乙二醇甲醚 为溶剂， 反应 43.0h， 生成 2-anilino-4-(2,4-dimethylthiazol-5-yl)pyrimidine
  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

文献信息

• THIAZOLES AS FUNGICIDES
  申请人：Greul Jorg Nico

  公开号：US20090030024A1

  公开（公告）日：2009-01-29

  Use of compounds of the formula (I), in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and X, Y, Z are as defined in the description as fungicides. Compounds of the formula (Ia), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 14 , A, X, Y and Z are as defined in the description, process for preparing these compounds and their use for controlling unwanted microorganisms.

  使用式(I)中的化合物，其中R1、R2、R3、R4、R5、R6、R7、R8以及X、Y、Z如描述中定义的作为杀菌剂。式(Ia)中的化合物，R1、R2、R3、R4、R5、R6、R7、R8、R14、A、X、Y和Z如描述中定义，制备这些化合物的方法以及它们用于控制不受欢迎的微生物的用途。
• Anti-viral compounds
  申请人：Wang Shudong

  公开号：US20050288307A1

  公开（公告）日：2005-12-29

  The present invention relates to the use of 2-substituted 4-heteroaryl-pyrimidines and related compounds in the treatment of viral disorders.

  本发明涉及使用2-取代的4-杂环基嘧啶和相关化合物治疗病毒性疾病。
• ANTI-VIRAL COMPOUNDS
  申请人：Cyclacel Limited

  公开号：EP1581231A1

  公开（公告）日：2005-10-05
• [EN] ANTI-VIRAL COMPOUNDS<br/>[FR] COMPOSES ANTIVIRAUX
  申请人：CYCLACEL LTD

  公开号：WO2004043467A1

  公开（公告）日：2004-05-27

  The present invention relates to the use of 2-substituted 4-heteroaryl-pyrimidines and related compounds of formula (I) in the treatment of viral disorders.
• 2-Anilino-4-(thiazol-5-yl)pyrimidine CDK Inhibitors:  Synthesis, SAR Analysis, X-ray Crystallography, and Biological Activity
  作者：Shudong Wang、Christopher Meades、Gavin Wood、Andrew Osnowski、Sian Anderson、Rhoda Yuill、Mark Thomas、Mokdad Mezna、Wayne Jackson、Carol Midgley、Gary Griffiths、Ian Fleming、Simon Green、Iain McNae、Su-Ying Wu、Campbell McInnes、Daniella Zheleva、Malcolm D. Walkinshaw、Peter M. Fischer

  DOI：10.1021/jm0309957

  日期：2004.3.1

  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.