(2R)-2-[[2-Bromo-5-[[(2-methyl-4-thiazolyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-propanol | 333743-42-3

• 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-Bromo-5-[[(2-methyl-4-thiazolyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-propanol
• 英文别名: (2R)-2-[[2-bromo-5-[(2-methyl-1,3-thiazol-4-yl)methylsulfanyl]-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]propan-1-ol
• CAS: 333743-42-3
• 化学式: C₁₃H₁₄BrN₅OS₃
• 分子量: 432.389
• InChiKey: XGMBSVRWDHOKTC-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  166
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2R)-2-[[2-Bromo-5-[[(2-methyl-4-thiazolyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-propanol 在 氢氧化钾 作用下， 以79%的产率得到(2R)-2-[[2-methoxy-5-[[(2-methyl-4-thiazolyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-propanol
  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：

  (2R)-2-[[2-Amino-5-[[(2-methyl-4-thiazolyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-propanol 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 (2R)-2-[[2-Bromo-5-[[(2-methyl-4-thiazolyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-propanol
  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

文献信息

• Novel thiazolo (4,5-D) pyrimidine compounds
  申请人：AstraZeneca UK Limited, a British corporation

  公开号：US20040224961A1

  公开（公告）日：2004-11-11

  The invention provides certain thiazolopyrimidine compounds of formula (I) or a pharmaceutically acceptable salt or solvate thereof; processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy. 1

  本发明提供式（I）的某些噻唑嘧啶化合物或其药学上可接受的盐或溶剂；用于它们的制备的过程和中间体，含有它们的制药组合物及其在治疗中的用途。
• NOVEL THIAZOLO (4,5-D) PYRIMIDINE COMPOUNDS NOVEL COMPOUNDS
  申请人：Willis Paul Andrew

  公开号：US20090281123A1

  公开（公告）日：2009-11-12

  The invention provides certain thiazolopyrimidine compounds of formula (I) or a pharmaceutically acceptable salt or solvate thereof, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy.

  该发明提供了式（I）的某些噻唑嘧啶化合物或其药学上可接受的盐或溶剂，用于制备它们的过程和中间体，含有它们的制药组合物以及它们在治疗中的应用。
• Thiazolo (4,5-D) pyrimidine compounds
  申请人：AstraZeneca UK Limited

  公开号：EP1348709A2

  公开（公告）日：2003-10-01

  The invention provides certain thiazolopyrimidine compounds of formula (I) or a pharmaceutically acceptable salt or solvate thereof; processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了某些式（I）的噻唑并嘧啶化合物或其药学上可接受的盐或溶液；用于制备它们的工艺和中间体，含有它们的药物组合物以及它们在治疗中的用途。
• Thiazolo[4,5-d]pyrimidine compounds for the treatment of rheumatoid arthritis
  申请人：AstraZeneca UK Limited

  公开号：EP1348709B1

  公开（公告）日：2008-01-16
• NOVEL THIAZOLO(4,5-D)PYRIMIDINE COMPOUNDS
  申请人：AstraZeneca UK Limited

  公开号：EP1222195B1

  公开（公告）日：2004-01-14