2,4-bis[[(2,3-difluorophenyl)methyl]thio]-7(8H)-pteridinone | 357612-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 2,4-bis[[(2,3-difluorophenyl)methyl]thio]-7(8H)-pteridinone
• 英文别名: 2,4-bis[(2,3-difluorophenyl)methylsulfanyl]-8H-pteridin-7-one
• CAS: 357612-93-2
• 化学式: C₂₀H₁₂F₄N₄OS₂
• 分子量: 464.467
• InChiKey: VWBPQIASVZZSLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,4-bis[[(2,3-difluorophenyl)methyl]thio]-7(8H)-pteridinone 、 D-氨基丙醇 在 乙酸乙酯 、 氯化铵 、 silica gel 、 甲醇 、 二氯甲烷 作用下， 反应 0.08h， 以methanol and then 1:1 DCM:ethyl acetate to yield the titled compound (220 mg)的产率得到2-(2,3 difluoro-benzylsulphanyl)-4-((R)-2-hydroxy-1-methyl-ethylamino)-8H-pteridin-7-one
  参考文献：
  名称：

  Pteridine compounds for the treatment of psoriasis

  摘要：

  本发明提供了公式(I)的黄素化合物，以及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。公式(I)中，A是公式(a)或(b)的基团。

  公开号：

  US20050171345A1
• 作为产物：
  描述：

  乙醛酸乙酯 、 2,6-bis[[(2,3-difluorophenyl)methyl]thio]-4,5-pyrimidinediamine 在 sodium 作用下， 以 甲醇 为溶剂， 以46%的产率得到2,4-bis[[(2,3-difluorophenyl)methyl]thio]-7(8H)-pteridinone
  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

• PTERIDINE COMPOUNDS FOR THE TREATMENT OF PSORIASIS
  申请人：AstraZeneca AB

  公开号：EP1259512A1

  公开（公告）日：2002-11-27
• US6875868B2
  申请人：——

  公开号：US6875868B2

  公开（公告）日：2005-04-05
• [EN] PTERIDINE COMPOUNDS FOR THE TREATMENT OF PSORIASIS<br/>[FR] COMPOSES DE PTERIDINE DESTINES AU TRAITEMENT DU PSORIASIS
  申请人：ASTRAZENECA AB

  公开号：WO2001062758A1

  公开（公告）日：2001-08-30

  The invention provides pteridine compounds of formula (I), 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) or (b).
• Pteridine compounds for the treatment of psoriasis
  申请人：——

  公开号：US20030055250A1

  公开（公告）日：2003-03-20

  The invention provides pteridine compounds of formula (I), 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) or (b).

  本发明提供了式(I)的蝶啶化合物，制备这些化合物的方法和中间体，含有这些化合物的药物组合物，以及它们在治疗中的用途。式(I)中，A为式(a)或式(b)的基团。
• 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.