(2R)-2-[[2-amino-5-[(3-chloro-2-fluorophenyl)methylsulfanyl]-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]propan-1-ol | 942408-19-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2R)-2-[[2-amino-5-[(3-chloro-2-fluorophenyl)methylsulfanyl]-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]propan-1-ol
• CAS: 942408-19-7
• 化学式: C₁₅H₁₅ClFN₅OS₂
• 分子量: 399.9
• InChiKey: FQIAAOXQRBGGTL-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R)-2-[[2-amino-5-[(3-chloro-2-fluorophenyl)methylsulfanyl]-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]propan-1-ol 在 三溴甲烷 、 亚硝酸异戊酯 作用下， 以 二甲基亚砜 为溶剂， 生成 (R)-2-((2-bromo-5-((3-chloro-2-fluorobenzyl)thio)thiazolo[4,5-d]pyrimidin-7-yl)amino)propan-1-ol
  参考文献：
  名称：

  Evaluation of a series of bicyclic CXCR2 antagonists

  摘要：

  The CXCR2 SAR of a series of bicyclic antagonists such as the 2-aminothiazolo[4,5-d]pyrimidine 3b was investigated by systematic variation of the fused pyrimidine-based heterocyclic cores. Replacement of the aminothiazole ring with a 2-thiazolone alternative led to a series of thiazolo[4,5-d]pyrimidine-2(3H)-one antagonists with markedly improved biological and pharmacokinetic properties, which are suitable pharmacological tools to probe the in vivo effects of CXCR2 antagonism combined with the associated CCR2 activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.039
• 作为产物：
  描述：

  (R)-2-[[2-Amino-5-[(phenylmethyl)thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-propanol 在 Oxone 、 sodium tetrahydroborate 作用下， 以 二甲基亚砜 为溶剂， 生成 (2R)-2-[[2-amino-5-[(3-chloro-2-fluorophenyl)methylsulfanyl]-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]propan-1-ol
  参考文献：
  名称：

  SAR studies on thiazolo[4,5-d]pyrimidine based CXCR2 antagonists involving a novel tandem displacement reaction

  摘要：

  As part of a Lead Optimisation programme to identify small molecule antagonists of the human CXCR2 receptor, a series of substituted thiazolo[4,5-d]pyrimidines was prepared via the application of a novel tandem displacement reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.080

文献信息

• SAR studies on thiazolo[4,5-d]pyrimidine based CXCR2 antagonists involving a novel tandem displacement reaction
  作者：Fraser Hunt、Caroline Austin、Rupert Austin、Roger Bonnert、Peter Cage、Jadeen Christie、Mark Christie、Clare Dixon、Steven Hill、Robert Jewell、Ian Martin、David Robinson、Paul Willis

  DOI：10.1016/j.bmcl.2007.02.080

  日期：2007.5

  As part of a Lead Optimisation programme to identify small molecule antagonists of the human CXCR2 receptor, a series of substituted thiazolo[4,5-d]pyrimidines was prepared via the application of a novel tandem displacement reaction. (c) 2007 Elsevier Ltd. All rights reserved.
• Evaluation of a series of bicyclic CXCR2 antagonists
  作者：Iain Walters、Caroline Austin、Rupert Austin、Roger Bonnert、Peter Cage、Mark Christie、Mark Ebden、Stuart Gardiner、Caroline Grahames、Steven Hill、Fraser Hunt、Robert Jewell、Shirley Lewis、Iain Martin、David Nicholls、David Robinson

  DOI：10.1016/j.bmcl.2007.11.039

  日期：2008.1

  The CXCR2 SAR of a series of bicyclic antagonists such as the 2-aminothiazolo[4,5-d]pyrimidine 3b was investigated by systematic variation of the fused pyrimidine-based heterocyclic cores. Replacement of the aminothiazole ring with a 2-thiazolone alternative led to a series of thiazolo[4,5-d]pyrimidine-2(3H)-one antagonists with markedly improved biological and pharmacokinetic properties, which are suitable pharmacological tools to probe the in vivo effects of CXCR2 antagonism combined with the associated CCR2 activity. (c) 2007 Elsevier Ltd. All rights reserved.