2-((2-amino-5-(benzylthio)thiazolo[4,5-d]pyrimidin-7-yl)amino)propane-1,3-diol | 333744-00-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-((2-amino-5-(benzylthio)thiazolo[4,5-d]pyrimidin-7-yl)amino)propane-1,3-diol
• 英文别名: 2-[[2-amino-5-[(phenylmethyl)thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1,3-propanediol；2-[(2-amino-5-benzylsulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]propane-1,3-diol
• CAS: 333744-00-6
• 化学式: C₁₅H₁₇N₅O₂S₂
• 分子量: 363.464
• InChiKey: AGVMIKGBXRDABU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  171
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-amino-5-[(phenylmethyl)thio]thiazolo[4,5-d]pyrimidin-7(4H)-one 在 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基苯胺 为溶剂， 反应 9.0h， 生成 2-((2-amino-5-(benzylthio)thiazolo[4,5-d]pyrimidin-7-yl)amino)propane-1,3-diol
  参考文献：
  名称：

  PB-10, a thiazolo[4,5-d] pyrimidine derivative, targets p21-activated kinase 4 in human colorectal cancer cells

  摘要：

  Targeting p21-activated kinase 4 (PAK4) is a potential therapeutic strategy against human colorectal cancer (CRC). In this study, we synthesized a series of novel thiazolo [4,5-d]pyrimidine derivatives (PB-1-12) and identified PB-10 (PAK4 IC50 = 15.12 mu M) as a potential and potent PAK4 inhibitor. Our results showed that PB10 significantly suppressed the proliferation and colony formation of human CRC cells. PB-10 also arrested HCT-116 CRC cells at sub G0/G1 phase while promoting the expression of proapoptotic proteins. In addition, PB-10 inhibited migration, invasion, and adhesion as well as the PAK4 downstream signaling pathway in HCT-116 cells. Molecular docking analysis showed possible binding modes between PB-10 and PAK4. Our study provides a novel compound that may block the PAK4 signaling in CRC cells.

  DOI：

  10.1016/j.bmcl.2019.126807

文献信息

• [EN] NOVEL THIAZOLO(4,5-D)PYRIMIDINE COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES DE THIAZOLO(4,5-D)PYRIMIDINE
  申请人：ASTRAZENECA UK LTD

  公开号：WO2001025242A1

  公开（公告）日：2001-04-12

  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.

  本发明提供了式（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，含有它们的药物组合物以及它们在治疗中的使用。
• 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 AB

  公开号：US08143261B2

  公开（公告）日：2012-03-27

  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.

  本发明提供公式（I）的某些噻唑嘧啶化合物或其药学上可接受的盐或溶剂，以及用于它们制备的过程和中间体，含有它们的制药组合物以及它们在治疗中的使用。
• 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