2-[2-(3,5-Dimethylanilino)pyrimidin-4-yl]-4-methyl-1,3-thiazole-5-carboxylic acid | 774230-49-8

• 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-[2-(3,5-Dimethylanilino)pyrimidin-4-yl]-4-methyl-1,3-thiazole-5-carboxylic acid
• CAS: 774230-49-8
• 化学式: C₁₇H₁₆N₄O₂S
• 分子量: 340.406
• InChiKey: ZPUOOGRVPLNSJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  L-氨基丙醇 、 2-[2-(3,5-Dimethylanilino)pyrimidin-4-yl]-4-methyl-1,3-thiazole-5-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-{2-[(3,5-dimethylphenyl)amino]pyrimidin-4-yl}-N-[(1S)-2-hydroxy-1-methylethyl]-4-methyl-1,3-thiazole-5-carboxamide
  参考文献：
  名称：

  Discovery and SAR of novel 4-thiazolyl-2-phenylaminopyrimidines as potent inhibitors of spleen tyrosine kinase (SYK)

  摘要：

  A series of SYK inhibitors based on the phenylamino pyrimidine thiazole lead 4 were prepared and evaluated for biological activity. Lead optimization provided compounds with nanomolar K(i)'s against SYK and potent inhibition in mast cell degranulation assays.

  DOI：

  10.1016/j.bmcl.2008.09.106
• 作为产物：
  描述：

  Ethyl 2-[2-(3,5-dimethylanilino)pyrimidin-4-yl]-4-methyl-1,3-thiazole-5-carboxylate 在 氢氧化钾 、 水 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 2-[2-(3,5-Dimethylanilino)pyrimidin-4-yl]-4-methyl-1,3-thiazole-5-carboxylic acid
  参考文献：
  名称：

  Discovery and SAR of novel 4-thiazolyl-2-phenylaminopyrimidines as potent inhibitors of spleen tyrosine kinase (SYK)

  摘要：

  A series of SYK inhibitors based on the phenylamino pyrimidine thiazole lead 4 were prepared and evaluated for biological activity. Lead optimization provided compounds with nanomolar K(i)'s against SYK and potent inhibition in mast cell degranulation assays.

  DOI：

  10.1016/j.bmcl.2008.09.106

文献信息

• THIAZOLES USEFUL AS INHIBITORS OF PROTEIN KINASES
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP1605946B1

  公开（公告）日：2008-05-28
• US7276502B2
  申请人：——

  公开号：US7276502B2

  公开（公告）日：2007-10-02
• Discovery and SAR of novel 4-thiazolyl-2-phenylaminopyrimidines as potent inhibitors of spleen tyrosine kinase (SYK)
  作者：Luc J. Farmer、Guy Bemis、Shawn D. Britt、John Cochran、Martin Connors、Edmund M. Harrington、Thomas Hoock、William Markland、Suganthini Nanthakumar、Paul Taslimi、Ernst Ter Haar、Jian Wang、Darshana Zhaveri、Francesco G. Salituro

  DOI：10.1016/j.bmcl.2008.09.106

  日期：2008.12

  A series of SYK inhibitors based on the phenylamino pyrimidine thiazole lead 4 were prepared and evaluated for biological activity. Lead optimization provided compounds with nanomolar K(i)'s against SYK and potent inhibition in mast cell degranulation assays.