4-Amino-6-chloro-5-nitro-2-[(phenylmethyl)thio]pyrimidine | 354582-78-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-Amino-6-chloro-5-nitro-2-[(phenylmethyl)thio]pyrimidine
• 英文别名: 6-chloro-5-nitro-2-[(phenylmethyl)thio]-4-pyrimidinamine；2-(Benzylthio)-6-chloro-5-nitropyrimidin-4-amine；2-benzylsulfanyl-6-chloro-5-nitropyrimidin-4-amine
• CAS: 354582-78-8
• 化学式: C₁₁H₉ClN₄O₂S
• 分子量: 296.737
• InChiKey: TWTMMICMISMLKM-UHFFFAOYSA-N

物化性质

• 沸点：
  515.9±50.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-Amino-6-chloro-5-nitro-2-[(phenylmethyl)thio]pyrimidine 在 铁粉 、 氯化铵 作用下， 以 乙醇 为溶剂， 生成 6-chloro-2-[(phenylmethyl)thio]-4,5-pyrimidinediamine
  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：

  4,6-Dichloro-5-nitro-2-[(phenylmethyl)thio]-pyrimidine 在 氨 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 以52%的产率得到4-Amino-6-chloro-5-nitro-2-[(phenylmethyl)thio]pyrimidine
  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

• Pyrimidine compounds and their use as modulators of chemokine receptor activity
  申请人：——

  公开号：US20030040523A1

  公开（公告）日：2003-02-27

  The invention provides certain heterocyclic compounds, processes, and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy; in formula (I), A is a group of formula (a) or (b).

  这项发明提供了某些杂环化合物，其制备过程和中间体，包含它们的药物组合物以及它们在治疗中的应用；在式（I）中，A是式（a）或（b）的基团。
• 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
• US6958344B2
  申请人：——

  公开号：US6958344B2

  公开（公告）日：2005-10-25
• [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).
• [EN] PYRIMIDINE COMPOUNDS AND THEIR USE AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] COMPOSES DE PYRIMIDE ET LEUR UTILISATION COMME MODULATEURS DE L'ACTIVITE DU RECEPTEUR DE CHIMIOKINE
  申请人：ASTRAZENECA AB

  公开号：WO2001058902A1

  公开（公告）日：2001-08-16

  The invention provides certain heterocyclic compounds, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy; in formula (I), A is a group of formula (a) or (b).