3-benzyl-7-chloro-5-methyl-1,2,3-triazolo[4,5-d]pyrimidine | 592520-20-2

• 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: 3-benzyl-7-chloro-5-methyl-1,2,3-triazolo[4,5-d]pyrimidine
• 英文别名: 3-benzyl-7-chloro-5-methyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine；3-benzyl-7-chloro-5-methyltriazolo[4,5-d]pyrimidine
• CAS: 592520-20-2
• 化学式: C₁₂H₁₀ClN₅
• 分子量: 259.698
• InChiKey: OJCNOAHTLRIWOK-UHFFFAOYSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzyl-7-chloro-5-methyl-1,2,3-triazolo[4,5-d]pyrimidine 在 氨 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 9-benzyl-2-methyl-8-azaadenine
  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-azapurin-6-one 在 N,N-二乙基苯胺 、 三氯氧磷 作用下， 反应 6.0h， 生成 3-benzyl-7-chloro-5-methyl-1,2,3-triazolo[4,5-d]pyrimidine
  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

文献信息

• 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。
• [EN] COMPOUNDS CONTAINING A N-HETEROARYL MOIETY LINKED TO FUSED RING MOIETIES FOR THE INHIBITION OF NAD(P)H OXIDASES AND PLATELET ACTIVATION<br/>[FR] COMPOSES COMPRENANT UNE FRACTION N-HETEROARYLE LIEE A DES FRACTIONS DE NOYAU FUSIONNEES ET DESTINES A L'INHIBITION DES NAD(P)H OXYDASES ET DE L'ACTIVATION DE PLAQUETTES
  申请人：VASOPHARM BIOTECH GMBH

  公开号：WO2005111041A1

  公开（公告）日：2005-11-24

  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.

  本发明涉及一种含有N-杂芳基基团的化合物，该基团通过氧、硫或氮或通过亚甲基桥和氧、硫或氮连接到融合环基团上，特别是1,2,3-三唑并[4,5-d]嘧啶-7-基自由基。本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该化合物的用途。
• 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。
• 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：EP1756113A1

  公开（公告）日：2007-02-28
• EP1756113B1
  申请人：——

  公开号：EP1756113B1

  公开（公告）日：2014-05-07