2,4-diamino-6-(4-methoxyphenyl)-pyrimidine | 17511-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,4-diamino-6-(4-methoxyphenyl)-pyrimidine
• 英文别名: 2,4-diamino-6-(4-methoxyphenyl)pyrimidine；6-(4-methoxyphenyl)pyrimidine-2,4-diamine；4-(4-methoxyphenyl)pyrimidin-2,6-diamine；6-(4-methoxy-phenyl)-pyrimidine-2,4-diamine
• CAS: 17511-19-2
• 化学式: C₁₁H₁₂N₄O
• 分子量: 216.242
• InChiKey: JVWGRSYEFVJHCX-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212 °C
• 沸点：
  522.1±60.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-二氯-6-(4-甲氧基苯基)嘧啶 在 氨 作用下， 以 乙醇 为溶剂， 以23.57%的产率得到2,4-diamino-6-(4-methoxyphenyl)-pyrimidine
  参考文献：
  名称：

  Identification of novel isocytosine derivatives as xanthine oxidase inhibitors from a set of virtual screening hits

  摘要：

  In recent years, xanthine oxidase has emerged as an important target not only for gout but also for cardiovascular and metabolic disorders involving hyperuricemia. Contrary to popular belief, recent clinical trials with uricosurics have demonstrated that enhanced excretion of uric acid is, by itself, not adequate to treat hyperuricemia; simultaneous inhibition of production of uric acid by inhibition of xanthine oxidase is also important. Virtual screening of in-house synthetic library followed by in vitro and in vivo testing led to the identification of a novel scaffold for xanthine oxidase inhibition. In vitro activity results corroborated the results from molecular docking studies of the virtual screening hits. The isocytosine scaffold maintains key hydrogen bonding and pi-stacking interactions in the deep end of the xanthine-binding pocket, which anchors it in an appropriate pose to inhibit binding of xanthine and shows promise for further lead optimization using structure-based drug design approach. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.019

文献信息

• A new method for the synthesis of 2,4-diamino-6-arylpyrimidines
  作者：V. G. Nenajdenko、I. V. Golubinskii、O. N. Lenkova、A. V. Shastin、E. S. Balenkova

  DOI：10.1007/s11172-005-0246-z

  日期：2005.1

  A method for the synthesis of 2,4-diamino-6-arylpyrimidines from guanidine and α-chlorocinnamonitriles was developed. The starting nitriles can be easily prepared by catalytic olefination reaction.

  从胍和α-氯肉桂腈合成2,4-二氨基-6-芳基嘧啶的方法已经开发出来。起始腈可以通过催化烯化反应轻松制备。
• Synthesis of 6-aryl-2,4-diamino-pyrimidines and triazines using palladium catalysed Suzuki cross-coupling reactions
  作者：Graeme Cooke、Hugues Augier de Cremiers、Vincent M Rotello、Brian Tarbit、Petra E Vanderstraeten

  DOI：10.1016/s0040-4020(01)00119-3

  日期：2001.4

  The high yielding synthesis of 6-aryl-2,4-diaminopyrimidines and triazines via palladium catalysed Suzuki cross-coupling reactions of commercially available 6-chloro-2,4-diaminopyrimidine 1 or 6-chloro-2,4-diaminotriazine 8 and aryl boronic acids are described. (C) 2001 Elsevier Science Ltd. All rights reserved.
• PYRIMIDINE, PYRIDINE, PTERIDINONE AND INDAZOLE DERIVATIVES AS ENZYME INHIBITORS
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0674627A1

  公开（公告）日：1995-10-04
• JPH08504798A
  申请人：——

  公开号：JPH08504798A

  公开（公告）日：1996-05-21
• [EN] PYRIMIDINE, PYRIDINE, PTERIDINONE AND INDAZOLE DERIVATIVES AS ENZYME INHIBITORS<br/>[FR] DERIVES DE PYRIMIDINE, DE PYRIDINE, DE PTERIDINONE ET D'INDAZOLE UTILISES COMME INHIBITEURS ENZYMATIQUES
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：WO1994014780A1

  公开（公告）日：1994-07-07

  (EN) The use of a compound which binds at the tetrahydrobiopterin site of NO synthase for the treatment of conditions where there is an advantage in inhibiting neuronal NO synthase with little or no inhibition of endothelial NO synthase is disclosed. Pharmaceutical formulations comprising such compounds, and processes, including a novel process, for their preparation are also disclosed.(FR) L'invention concerne l'utilisation d'un composé qui se lie au site de tétrahydrobioptérine de la NO synthétase pour le traitement d'états dans lesquels il est bénéfique d'inhiber la NO synthétase neuronale avec peu ou pas d'inhibition de la NO synthétase endothéliale. L'invention concerne également des formulations pharmaceutiques contenant de tels composés et des procédés, y compris un nouveau procédé, pour leur préparation.