1-bromo-2-[(1S)-1-chloroethyl]benzene | 1429127-79-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-bromo-2-[(1S)-1-chloroethyl]benzene
• CAS: 1429127-79-6
• 化学式: C₈H₈BrCl
• 分子量: 219.509
• InChiKey: JJYCAISWXYBWPK-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(2-amino-5-sulfanyl[1,3]thiazolo[4,5-d]pyrimidin-7-yl)-amino]-4-methylpentan-1-ol 、 1-bromo-2-[(1S)-1-chloroethyl]benzene 在 sodium tetrahydroborate 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 以11%的产率得到(2R)-2-[[2-amino-5-[(1R)-1-(2-bromophenyl)ethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-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：

  (R)-(+)-2-溴-α-甲基苯甲醇 在 三苯基膦 、 lithium chloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到1-bromo-2-[(1S)-1-chloroethyl]benzene
  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