(2R)-2-[[2-Amino-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-butanol

• 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-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-butanol
• 英文别名: (R)-2-(5-(2,3-difluorobenzylthio)-2-aminothiazolo[4,5-d]pyrimidin-7-ylamino)butan-1-ol；(2R)-2-[[2-amino-5-[(2,3-difluorophenyl)methylsulfanyl]-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]butan-1-ol
• 化学式: C₁₆H₁₇F₂N₅OS₂
• 分子量: 397.473
• InChiKey: RWUQUOUNNCHFDU-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-amino-5-[(phenylmethyl)thio]thiazolo[4,5-d]pyrimidin-7(4H)-one 在 aluminum tri-bromide 、 potassium tert-butylate 、 三氯氧磷 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 80.0h， 生成 (2R)-2-[[2-Amino-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-butanol
  参考文献：
  名称：

  Hit-to-Lead studies: The discovery of potent, orally bioavailable thiazolopyrimidine CXCR2 receptor antagonists

  摘要：

  A Hit-to-Lead optimisation programme was carried out on a high throughput screening hit, the thiazolopyrimidine 1, resulting in the discovery of the potent, orally bioavailable CXCR2 antagonist 29. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.091

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.
• NOVEL THIAZOLOPYRIMIDINE COMPOUNDS
  申请人：AstraZeneca AB

  公开号：EP1104425B1

  公开（公告）日：2003-01-29
• US6806273B1
  申请人：——

  公开号：US6806273B1

  公开（公告）日：2004-10-19
• [EN] NOVEL THIAZOLOPYRIMIDINE COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES DE THIAZOLOPYRIMIDINE
  申请人：ASTRA PHARMA PROD

  公开号：WO2000009511A1

  公开（公告）日：2000-02-24

  The invention provides certain thiazolopyrimidine compounds of general formula (I), processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy.
• Hit-to-Lead studies: The discovery of potent, orally bioavailable thiazolopyrimidine CXCR2 receptor antagonists
  作者：Andrew Baxter、Anne Cooper、Elizabeth Kinchin、Kerry Moakes、John Unitt、Alan Wallace

  DOI：10.1016/j.bmcl.2005.10.091

  日期：2006.2

  A Hit-to-Lead optimisation programme was carried out on a high throughput screening hit, the thiazolopyrimidine 1, resulting in the discovery of the potent, orally bioavailable CXCR2 antagonist 29. (c) 2005 Elsevier Ltd. All rights reserved.