4-(2,5-dichloro-anilino)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester | 107920-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(2,5-dichloro-anilino)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester
• 英文别名: 4-(2,5-Dichlor-anilino)-2-methylmercapto-pyrimidin-5-carbonsaeure-aethylester
• CAS: 107920-52-5
• 化学式: C₁₄H₁₃Cl₂N₃O₂S
• 分子量: 358.248
• InChiKey: WJYAERLHFDPEDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  64.11
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(2,5-dichloro-anilino)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester 在 氯化亚砜 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 [4-(2,5-dichloroanilino)pyrimidin-5-yl]-(3,4-dihydro-2H-quinolin-1-yl)methanone
  参考文献：
  名称：

  Discovery of novel pyrimidine and malonamide derivatives as TGR5 agonists

  摘要：

  Takeda G-protein-coupled receptor 5 (TGR5) is a promising molecular target for metabolic diseases. A series of 4-(2,5-dichlorophenoxy)pyrimidine and cyclopropylmalonamide derivatives were synthesized as potent agonists of TGR5 based on a bioisosteric replacement strategy. Several compounds exhibited improved potency, compared to a reference compound with a pyridine scaffold. The pharmacokinetic profile of the representative compound 18 was considered moderate.

  DOI：

  10.1016/j.bmcl.2014.07.026
• 作为产物：
  描述：

  2,5-二氯苯胺 、 4-氯-2-甲硫基嘧啶-5-羧酸乙酯 在 N,N-二异丙基乙胺 作用下， 以 叔丁醇 为溶剂， 以85%的产率得到4-(2,5-dichloro-anilino)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Discovery of novel pyrimidine and malonamide derivatives as TGR5 agonists

  摘要：

  Takeda G-protein-coupled receptor 5 (TGR5) is a promising molecular target for metabolic diseases. A series of 4-(2,5-dichlorophenoxy)pyrimidine and cyclopropylmalonamide derivatives were synthesized as potent agonists of TGR5 based on a bioisosteric replacement strategy. Several compounds exhibited improved potency, compared to a reference compound with a pyridine scaffold. The pharmacokinetic profile of the representative compound 18 was considered moderate.

  DOI：

  10.1016/j.bmcl.2014.07.026