9-benzyl-2-methyl-8-azapurin-6-one | 71492-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 9-benzyl-2-methyl-8-azapurin-6-one
• 英文别名: 3-benzyl-5-methyl-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one；9-Benzyl-2-methyl-8-azapurin-6-on；3-Benzyl-5-methyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol；3-benzyl-5-methyl-6H-triazolo[4,5-d]pyrimidin-7-one
• CAS: 71492-05-2
• 化学式: C₁₂H₁₁N₅O
• mdl: MFCD03753698
• 分子量: 241.252
• InChiKey: LHLLYOFPMYOQAO-UHFFFAOYSA-N

物化性质

• 熔点：
  185-187 °C
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-benzyl-2-methyl-8-azapurin-6-one 在 氨 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  2,9-Disubstituted-N6-(arylcarbamoyl)-8-azaadenines as new selective A3 adenosine receptor antagonists: Synthesis, biochemical and molecular modelling studies

  摘要：

  A number of N-6-(N-arylcarbamoyl)-2-substituted-9-benzyl-8-azaadenines, obtained by a modification of the synthetic scheme used to prepare selective A(1) ligands, by only three or two steps, are described. At first we prepared a series of 2-phenyl-9-benzyl-8-azaadenines having as N-6 substituent a variously substituted N-phenylcarbamoyl group. Some of these derivatives demonstrated good affinity towards the A(3) subtype but low selectivity. Compounds having p-CF3, p-F and p-OCH3, as substituents on the phenylcarbamoyl group were selected as lead compounds for the second part of this study. Without modifying the N-6 substituent, which would assure A(3) affinity, we varied the 9 and 2 positions on these molecules to enhance selectivity. Some compounds having a p-methyl group on the 2-phenyl substituent showed a very good affinity and selectivity for the A(3) subtype, revealing the first class of A(3) adenosine receptor selective antagonists with a bicyclic structure strictly correlated to the adenine nucleus. The molecular modelling work, carried out using the DOCK program, supplied two models which may be useful for a better understanding of the binding modes. Both models highlighted the preferred interacting tautomeric forms of the antagonists for human A(1) and A(3) receptors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.063
• 作为产物：
  描述：

  9-benzyl-2-methyl-8-azapurine 以 水 为溶剂， 以38%的产率得到9-benzyl-2-methyl-8-azapurin-6-one
  参考文献：
  名称：

  Kazmierczak, Franciszek, Polish Journal of Chemistry, 1980, vol. 54, # 6, p. 1333 - 1334

  摘要：

  DOI：

文献信息

• A facile “one pot” synthesis of 2,9-disubstituted 8-azapurin-6-ones (3,5-disubstituted 7-hydroxy-3<i>H</i>-1,2,3-triazolo[4,5-<i>d</i>]pyrimidines)
  作者：Pier Luigi Barili、Giuliana Biagi、Oreste Livi、Valerio Scartoni

  DOI：10.1002/jhet.5570220628

  日期：1985.11

  A series of title compounds have been synthesized by utilising benzylazide, cyanoacetamide, ethyl or methyl esters of aliphatic or aromatic carboxylic acids and sodium ethoxide as catalyst.

  利用苄基叠氮化物，氰基乙酰胺，脂族或芳族羧酸的乙酯或甲酯和乙醇钠合成了一系列标题化合物。
• Compounds containing a N-heteroaryl moiety linked to fused ring moieties for the inhibition of NAD(P)H oxidases and platelet activation
  申请人：Vasopharm Biotech GmbH

  公开号：EP1598354A1

  公开（公告）日：2005-11-23

  The invention relates to compounds containing a N-heteroaryl moiety, which is linked via oxygen, sulfur or nitrogen, or via a methylene bridge and oxygen, sulfur or nitrogen to a fused ring moiety, in particular to the 1,2,3-triazolo[4,5-d]pyrimidine-7-yl radical. The invention also relates to a process for the preparation of said compounds and the use thereof in drugs for the treatment of NAD(P)H oxidases-related diseases and disorders and inhibition of platelet activation.

  该发明涉及含有N-杂环芳基团的化合物，该化合物通过氧、硫或氮，或通过亚甲基桥和氧、硫或氮连接到融合环基团，特别是到1,2,3-三唑并[4,5-d]嘧啶-7-基自由基。该发明还涉及一种制备所述化合物的方法以及在治疗NAD(P)H氧化酶相关疾病和疾病以及抑制血小板活化的药物中的使用。
• Compounds Containing a N-Heteroaryl Moiety Linked to Fused Ring Moieties for the Inhibition of Nad(P)H Oxidases and Platelet Activation
  申请人：Tegtmeier Frank

  公开号：US20080044354A1

  公开（公告）日：2008-02-21

  The invention relates to compounds containing a N-heteroaryl moiety, which is linked via oxygen, sulfur or nitrogen, or via a methylene bridge and oxygen, sulfur or nitrogen to a fused ring moiety, in particular to the 1,2,3-triazolo[4,5d]pyrimidine-7-yl radical. The invention also relates to a process for the preparation of said compounds and the use thereof in drugs for the treatment of NAD(P)H oxidases-related diseases and disorders and inhibition of platelet activation.

  该发明涉及含有N-杂环芳基基团的化合物，该基团通过氧、硫或氮或通过亚甲基桥和氧、硫或氮连接到一个融合环基团上，特别是1,2,3-三唑并[4,5d]嘧啶-7-基自由基。该发明还涉及制备该化合物的方法以及在治疗NAD（P）H氧化酶相关疾病和障碍以及抑制血小板活化的药物中使用它们的用途。
• Three-Step Synthetic Pathway toward Fully Decorated [1,2,3]Triazolo[4,5-<i>d</i>]pyrimidine (8-Azapurine) Derivatives
  作者：Felien Reniers、Stijn Anthonissen、Luc Van Meervelt、Wim Dehaen

  DOI：10.1021/acs.orglett.3c00729

  日期：2023.4.28

  5-d]pyrimidines (8-azapurines) are known bioisosteres of the purine nucleus. A step-efficient synthesis of 8-azapurines, in particular 6-alkyl derivatives, is currently unavailable. This work focuses on a three-step synthetic pathway for the synthesis of fully decorated 8-azapurines, with special attention on 6-alkyl-8-azapurines. A diverse library of 8-azapurines was obtained starting from various alkynes

  [1,2,3]三唑并[4,5- d ]嘧啶（8-氮杂嘌呤）是已知的嘌呤核生物电子等排物。目前无法有效地合成 8-氮杂嘌呤，特别是 6-烷基衍生物。这项工作侧重于合成完全修饰的 8-氮杂嘌呤的三步合成途径，特别关注 6-烷基-8-氮杂嘌呤。从各种炔烃、叠氮化物和脒开始，获得了一个多样化的 8-氮杂嘌呤库，涉及中断的 CuAAC、氧化和环化反应。此外，对选定数量的底物进行了后功能化反应。
• ——
  作者：V. P. Kislyi、E. B. Danilova、V. V. Semenov

  DOI：10.1023/a:1026004720790

  日期：——

  The reactions of N-substituted 4-amino-3-benzyl-1,2,3-triazole-5-carboxamides with phosphorus oxochloride and dimethylformamide at 80 degreesC or with triethyl orthoacetate and acetic anhydride at 160 degreesC afforded 6-mono- or 5,6-disubstituted 1,2,3-triazolo[4.5-d]pyrimidin-7-ones in 30-85% and 65-90% yields, respectively.