4,5-二氨基-6-氯-2-苯基嘧啶 | 424830-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 4,5-二氨基-6-氯-2-苯基嘧啶
• 英文名称: 6-chloro-2-phenylpyrimidine-4,5-diamine
• 英文别名: 6-Chloro-2-phenyl-pyrimidine-4,5-diamine
• CAS: 424830-76-2
• 化学式: C₁₀H₉ClN₄
• 分子量: 220.661
• InChiKey: BSMPQPRDZDMGKR-UHFFFAOYSA-N

物化性质

• 沸点：
  294.8±40.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-二氨基-6-氯-2-苯基嘧啶 在 potassium nitrite 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以53%的产率得到6-chloro-2-phenyl-9H-8-azapurine
  参考文献：
  名称：

  erythro- and threo-2-Hydroxynonyl substituted 2-phenyladenines and 2-phenyl-8-azaadenines: ligands for A1 adenosine receptors and adenosine deaminase

  摘要：

  erythro-2-Phenyl-9-(2-hydroxy-3-nonyl)adenine and its 8-aza analog were prepared and showed a very high inhibitory activity towards adenosine deaminase (ADA), with K-i 0.55 and 1.67 nM, respectively, and high affinity for A, adenosine receptors, with K-i 28 and 2.8 nM, respectively. To increase affinity for A(1) receptors we introduced a substituent on the N-6 position such as alkyl or cycloalkyl groups, which are present in effective agonists or antagonists. Furthermore, for some compounds, we prepared the two diastereoisomers erythro and threo to verify whether the binding with A(1) receptors is stereoselective, as in ADA. Results show that some of the synthesised compounds are good inhibitors for ADA and good ligands for A(1), and the erythro diastereoisomers are more active than the threo ones. The experimental evidence allows us to hypothesise some similarity in the three dimensional structures of the binding site of the two proteins, ADA and A(1) adenosine receptor, in spite of lacking any homologies in the aminoacid sequences. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01200-4
• 作为产物：
  描述：

  4,6-二氯-5-硝基-2-苯基嘧啶 在 氨 、 铁粉 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 73.5h， 生成 4,5-二氨基-6-氯-2-苯基嘧啶
  参考文献：
  名称：

  erythro- and threo-2-Hydroxynonyl substituted 2-phenyladenines and 2-phenyl-8-azaadenines: ligands for A1 adenosine receptors and adenosine deaminase

  摘要：

  erythro-2-Phenyl-9-(2-hydroxy-3-nonyl)adenine and its 8-aza analog were prepared and showed a very high inhibitory activity towards adenosine deaminase (ADA), with K-i 0.55 and 1.67 nM, respectively, and high affinity for A, adenosine receptors, with K-i 28 and 2.8 nM, respectively. To increase affinity for A(1) receptors we introduced a substituent on the N-6 position such as alkyl or cycloalkyl groups, which are present in effective agonists or antagonists. Furthermore, for some compounds, we prepared the two diastereoisomers erythro and threo to verify whether the binding with A(1) receptors is stereoselective, as in ADA. Results show that some of the synthesised compounds are good inhibitors for ADA and good ligands for A(1), and the erythro diastereoisomers are more active than the threo ones. The experimental evidence allows us to hypothesise some similarity in the three dimensional structures of the binding site of the two proteins, ADA and A(1) adenosine receptor, in spite of lacking any homologies in the aminoacid sequences. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01200-4

文献信息

• Synthesis of New 2-Phenyladenines and 2-Phenylpteridines and Biological Evaluation as Adenosine Receptor Ligands
  作者：Irene Giorgi、Giuliana Biagi、Oreste Livi、Michele Leonardi、Valerio Scartoni、Daniele Pietra

  DOI：10.1002/ardp.200600168

  日期：2007.2

  maintain high activity towards adenosine receptors; in fact, pteridine derivatives did not show themselves to be good adenosine receptor ligands. On the contrary, N6‐cycloalkyl‐ or N6‐alkyl‐2‐phenyladenines showed a very high affinity and selectivity for A1 adenosine receptors. We demonstrate also that the 9‐benzyl substituent is crucial for conferring high affinity for A3 receptors to molecules having a

  描述了一系列 2-苯基蝶啶衍生物的合成和生物测定，以将它们对腺苷受体的亲和力与特意制备的相应腺嘌呤和先前描述的 8-氮杂腺嘌呤的亲和力进行比较。这项研究表明，腺嘌呤核的五元环扩大为六元环是一种修饰，不允许分子保持对腺苷受体的高活性；事实上，蝶啶衍生物本身并不是良好的腺苷受体配体。相反，N6-环烷基-或N6-烷基-2-苯基腺嘌呤对A1腺苷受体表现出非常高的亲和力和选择性。我们还证明了 9-苄基取代基对于将 A3 受体的高亲和力赋予具有 2-苯腺嘌呤样核的分子至关重要。
• 2,6-Disubstituted and 2,6,8-Trisubstituted Purines as Adenosine Receptor Antagonists
  作者：Lisa C. W. Chang、Ronald F. Spanjersberg、Jacobien K. von Frijtag Drabbe Künzel、Thea Mulder-Krieger、Johannes Brussee、Adriaan P. IJzerman

  DOI：10.1021/jm050640i

  日期：2006.5.1

  Purines have long been exploited as adenosine receptor antagonists. The substitution pattern about the purine ring has been well investigated, and certain criteria have become almost a prerequisite for good affinity at the adenosine A(1) receptor. The adaptation of the pharmacophore and the initial series of pyrimidines developed in an earlier publication resulted in a series of purines with an entirely

  嘌呤长期以来被用作腺苷受体拮抗剂。嘌呤环的取代模式已得到很好的研究，并且某些标准几乎已经成为在腺苷A（1）受体上具有良好亲和力的前提。在较早的出版物中开发的药效基团和最初的嘧啶系列适用于此，从而产生了一系列具有全新取代模式的嘌呤。一种化合物，特别是8-环戊基-2,6-二苯基嘌呤（31，LUF 5962）已被证明是非常有前途的，对人腺苷A（1）受体的亲和力为0.29 nM。
• [EN] HETEROCYCLIC COMPOUNDS FOR ORGANIC ELECTROLUMINESCENT DEVICES<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES POUR DISPOSITIFS ÉLECTROLUMINESCENTS ORGANIQUES<br/>[DE] HETEROCYCLISCHE VERBINDUNGEN FÜR ORGANISCHE ELEKTROLUMINESZENZVORRICHTUNGEN
  申请人：[de]MERCK PATENT GMBH

  公开号：WO2022117473A1

  公开（公告）日：2022-06-09

  Die vorliegende Erfindung betrifft heterocyclische Verbindungen, die sich für die Verwendung in elektronischen Vorrichtungen eignen, sowie elektronische Vorrichtungen, insbesondere organischen Elektrolumineszenzvorrichtungen, enthaltend diese Verbindungen.