Ethyl 4-(2,5-dichlorophenoxy)-2-(methylsulfanyl)-5-pyrimidinecarboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 4-(2,5-dichlorophenoxy)-2-(methylsulfanyl)-5-pyrimidinecarboxylate
• 英文别名: ethyl 4-(2,5-dichlorophenoxy)-2-methylsulfanylpyrimidine-5-carboxylate
• 化学式: C₁₄H₁₂Cl₂N₂O₃S
• 分子量: 359.233
• InChiKey: HLPCYGLYOFNHQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  86.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(2,5-dichlorophenoxy)-2-(methylsulfanyl)-5-pyrimidinecarboxylate 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-dichloro-phenoxy)-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：

  4-氯-2-甲硫基嘧啶-5-羧酸乙酯 、 2,5-二氯苯酚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到Ethyl 4-(2,5-dichlorophenoxy)-2-(methylsulfanyl)-5-pyrimidinecarboxylate
  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

文献信息

• Discovery of novel pyrimidine and malonamide derivatives as TGR5 agonists
  作者：Eun Ju Park、Young Gil Ahn、Seung Hyun Jung、Hyo Jeong Bang、Mira Kim、Dong Jin Hong、Jisook Kim、Kwee Hyun Suh、Young Jin Kim、Doran Kim、Eun-Yeong Kim、Kiho Lee、Kyung Hoon Min

  DOI：10.1016/j.bmcl.2014.07.026

  日期：2014.9

  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.