7-chloro-5-[(2-chlorobenzyl)sulfanyl][1,3]thiazolo[4,5-d]pyrimidin-2-amine | 1429127-85-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 7-chloro-5-[(2-chlorobenzyl)sulfanyl][1,3]thiazolo[4,5-d]pyrimidin-2-amine
• CAS: 1429127-85-4
• 化学式: C₁₂H₈Cl₂N₄S₂
• 分子量: 343.26
• InChiKey: CBLPZRTZTIVNPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  64.69
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl [(3R)-1-hydroxy-5-methylhexan-3-yl]carbamate 、 7-chloro-5-[(2-chlorobenzyl)sulfanyl][1,3]thiazolo[4,5-d]pyrimidin-2-amine 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以6%的产率得到(3S)-3-({2-amino-5-[(2-chlorobenzyl)sulfanyl][1,3]thiazolo[4,5-d]pyrimidin-7-yl}amino)-5-methylhexan-1-ol
  参考文献：
  名称：

  Substituted 7-Amino-5-thio-thiazolo[4,5-d]pyrimidines as Potent and Selective Antagonists of the Fractalkine Receptor (CX₃CR1)

  摘要：

  We have developed two parallel series, A and B, of CX(3)CR1 antagonists for the treatment of multiple sclerosis. By modifying the substituents on the 7-amino-5-thio-thiazolo[4,5-d]-pyrimidine core structure, we were able to achieve compounds with high selectivity for CX(3)CR1 over the closely related CXCR2 receptor. The structure-activity relationships showed that a leucinol moiety attached to the core-structure in the 7-position together with alpha-methyl branched benzyl derivatives in the 5-position displayed promising affinity, and selectivity as well as physicochemical properties, as exemplified by compounds 18a and 24h. We show the preparation of the first potent and selective orally available CX(3)CR1 antagonists.

  DOI：

  10.1021/jm3012273
• 作为产物：
  描述：

  2-(ortho-chlorobenzylthio)-6-aminouracil 在 吡啶 、 溴 、 三氯氧磷 作用下， 以 N,N-二甲基苯胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.17h， 生成 7-chloro-5-[(2-chlorobenzyl)sulfanyl][1,3]thiazolo[4,5-d]pyrimidin-2-amine
  参考文献：
  名称：

  Substituted 7-Amino-5-thio-thiazolo[4,5-d]pyrimidines as Potent and Selective Antagonists of the Fractalkine Receptor (CX₃CR1)

  摘要：

  We have developed two parallel series, A and B, of CX(3)CR1 antagonists for the treatment of multiple sclerosis. By modifying the substituents on the 7-amino-5-thio-thiazolo[4,5-d]-pyrimidine core structure, we were able to achieve compounds with high selectivity for CX(3)CR1 over the closely related CXCR2 receptor. The structure-activity relationships showed that a leucinol moiety attached to the core-structure in the 7-position together with alpha-methyl branched benzyl derivatives in the 5-position displayed promising affinity, and selectivity as well as physicochemical properties, as exemplified by compounds 18a and 24h. We show the preparation of the first potent and selective orally available CX(3)CR1 antagonists.

  DOI：

  10.1021/jm3012273