4-[2-amino-6-(3,4-dimethoxyphenyl)pteridin-4-yl]-N-[(4-fluorophenyl)methyl]piperazine-1-carboxamide | 851315-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-[2-amino-6-(3,4-dimethoxyphenyl)pteridin-4-yl]-N-[(4-fluorophenyl)methyl]piperazine-1-carboxamide
• CAS: 851315-91-8
• 化学式: C₂₆H₂₇FN₈O₃
• 分子量: 518.551
• InChiKey: WEIQKOLKYRYHGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-amino-4-N-piperazinyl-6-(3,4-dimethoxyphenyl)-pteridine 、 4-氟代苯异氰酸盐 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-[2-amino-6-(3,4-dimethoxyphenyl)pteridin-4-yl]-N-[(4-fluorophenyl)methyl]piperazine-1-carboxamide
  参考文献：
  名称：

  Synthesis and in vitro evaluation of 2-amino-4-N-piperazinyl-6-(3,4-dimethoxyphenyl)-pteridines as dual immunosuppressive and anti-inflammatory agents

  摘要：

  Screening of a pteridine-based compound library led to the identification of compounds exhibiting immunosuppressive as well as anti-inflammatory activity. Optimization afforded a series of 2-amino-4-N-piperazinyl-6-(3,4-dimethoxyphenyl)pteridine analogues. The most potent congeners in this series displayed low nM IC50 values in the Mixed Lymphocyte Reaction (MLR) assay. In addition, these compounds also have potent anti-inflammatory activity as measured in the Tumor Necrosis Factor (TNF) assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.053

文献信息

• Pteridine derivatives useful for making pharmaceutical compositions
  申请人：Waer Jozef Albert Mark

  公开号：US20070032477A1

  公开（公告）日：2007-02-08

  This invention relates to a group of substituted pteridine derivatives, their pharmaceutically acceptable salts, N-oxides, solvates, dihydro- and tetrahydro-derivatives, and enantiomers, possessing unexpectedly desirable pharmaceutical properties, in particular which are highly active immunosuppressive agents, and as such are useful in the treatment in transplant rejection and/or in the treatment of certain inflammatory diseases. These derivatives are also useful in preventing or treating cardiovascular disorders, allergic conditions, disorders of the central nervous system, TNF-α related disorders, viral diseases, inflammatory bowel diseases and cell proliferative disorders.

  本发明涉及一类取代的喹噁啉衍生物，其药学上可接受的盐、N-氧化物、溶剂合物、二氢和四氢衍生物以及对映体，具有出乎意料的理想药理特性，尤其是高活性的免疫抑制剂，因此在移植排斥和/或某些炎症性疾病的治疗中非常有用。这些衍生物还可用于预防或治疗心血管疾病、过敏性疾病、中枢神经系统疾病、TNF-α相关疾病、病毒性疾病、炎症性肠病和细胞增殖性疾病。
• HETEROCYCLE-SUBSTITUTED PTERIDINE DERIVATIVES AND THEIR USE IN THERAPY
  申请人：4 AZA IP NV

  公开号：EP1673092B1

  公开（公告）日：2007-08-15
• Synthesis and in vitro evaluation of 2-amino-4-N-piperazinyl-6-(3,4-dimethoxyphenyl)-pteridines as dual immunosuppressive and anti-inflammatory agents
  作者：Steven De Jonghe、Arnaud Marchand、Ling-Jie Gao、Agnes Calleja、Eva Cuveliers、Ilse Sienaert、Jean Herman、Gavin Clydesdale、Hassane Sefrioui、Yuan Lin、Wolfgang Pfleiderer、Mark Waer、Piet Herdewijn

  DOI：10.1016/j.bmcl.2010.11.053

  日期：2011.1

  Screening of a pteridine-based compound library led to the identification of compounds exhibiting immunosuppressive as well as anti-inflammatory activity. Optimization afforded a series of 2-amino-4-N-piperazinyl-6-(3,4-dimethoxyphenyl)pteridine analogues. The most potent congeners in this series displayed low nM IC50 values in the Mixed Lymphocyte Reaction (MLR) assay. In addition, these compounds also have potent anti-inflammatory activity as measured in the Tumor Necrosis Factor (TNF) assay. (C) 2010 Elsevier Ltd. All rights reserved.