(2R)-2-[[6-chloro-5-nitro-2-[[phenylmethyl]thio]pyrimidin-4-yl]amino]-1-propanol | 354822-24-5

• 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-[[6-chloro-5-nitro-2-[[phenylmethyl]thio]pyrimidin-4-yl]amino]-1-propanol
• 英文别名: (2R)-2-[(2-benzylsulfanyl-6-chloro-5-nitropyrimidin-4-yl)amino]propan-1-ol
• CAS: 354822-24-5
• 化学式: C₁₄H₁₅ClN₄O₃S
• 分子量: 354.817
• InChiKey: RNCFNRCFEYYMQO-SECBINFHSA-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：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R)-2-[[6-chloro-5-nitro-2-[[phenylmethyl]thio]pyrimidin-4-yl]amino]-1-propanol 、 potassium thioacyanate 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 18.0h， 生成 (2R)-2-[[5-Nitro-2-[[phenylmethyl]thio]-6-thiocyanatopyrimidin-4-yl]amino]-1-propanol
  参考文献：
  名称：

  PYRIMIDINE COMPOUNDS AND THEIR USE AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

  摘要：

  公开号：

  EP1257555B1
• 作为产物：
  描述：

  4,6-Dichloro-5-nitro-2-[(phenylmethyl)thio]-pyrimidine 、 D-氨基丙醇 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到(2R)-2-[[6-chloro-5-nitro-2-[[phenylmethyl]thio]pyrimidin-4-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

• [EN] PYRIMIDINE COMPOUNDS AND THEIR USE AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] COMPOSES PYRIMIDINIQUES ET LEUR UTILISATION COMME MODULATEURS DE L'ACTIVITE DES RECEPTEURS DE CHIMIOKINE
  申请人：ASTRAZENECA AB

  公开号：WO2001058906A1

  公开（公告）日：2001-08-16

  The invention provides certain pyrimidine compounds, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy. Formula (I) in which: A is a group of formula (a), (b) or (c).
• PYRIMIDINE COMPOUNDS AND THEIR USE AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：AstraZeneca AB

  公开号：EP1257555B1

  公开（公告）日：2003-12-03
• 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.