2-(7H-嘌呤-6-基)胍 | 446839-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-(7H-嘌呤-6-基)胍
• 英文名称: 6-guanidinopurine
• 英文别名: 2-(7H-purin-6-yl)guanidine
• CAS: 446839-81-2
• 化学式: C₆H₇N₇
• 分子量: 177.168
• InChiKey: WDNNRYVUSSAUPC-UHFFFAOYSA-N

物化性质

• 沸点：
  519.5±53.0 °C(Predicted)
• 密度：
  1.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 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：
  119
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(7H-嘌呤-6-基)胍 在 三甲基溴硅烷 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 15.0h， 生成 7-[2-(phosphonomethoxy)ethyl]-6-guanidino-7H-purine
  参考文献：
  名称：

  6-Guanidinopurine nucleosides and their analogues

  摘要：

  A general synthetic approach to 6-guanidinopurines, their ribonucleosides, 2-deoxyribonucleosides, acyclic nucleoside analogues and acyclic nucleoside phosphonates was developed. The approach consists in the reaction of the 6-chloropurine derivatives with guanidine solution in DMF under DABCO catalysis. This method was used to synthesize 6-guanidinopurine and 2-amino-6-guanidinopurine derivatives. Acyclic nucleosides and acyclic nucleoside phosphonates were also obtained by alkylation of the 6-guanidinopurine bases. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00186-2
• 作为产物：
  描述：

  盐酸胍 、 6-氯-9-(四氢-2-吡喃基)嘌呤 在 sodium hydride 、 1,4-diazabicyclooctane 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 以72%的产率得到2-(7H-嘌呤-6-基)胍
  参考文献：
  名称：

  6-Guanidinopurine nucleosides and their analogues

  摘要：

  A general synthetic approach to 6-guanidinopurines, their ribonucleosides, 2-deoxyribonucleosides, acyclic nucleoside analogues and acyclic nucleoside phosphonates was developed. The approach consists in the reaction of the 6-chloropurine derivatives with guanidine solution in DMF under DABCO catalysis. This method was used to synthesize 6-guanidinopurine and 2-amino-6-guanidinopurine derivatives. Acyclic nucleosides and acyclic nucleoside phosphonates were also obtained by alkylation of the 6-guanidinopurine bases. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00186-2

文献信息

• Synthesis of guanidino analogues of PMPDAP and their immunobiological activity
  作者：Michal Česnek、Antonín Holý、Milena Masojídková、Eva Kmoníčková、Zdeněk Zídek

  DOI：10.1016/j.bmc.2007.10.010

  日期：2008.1

  A series of novel 9-, 7- and 3-substituted 2- or 6-guanidinopurines as analogues of potent antiviral and immunobiologically active compound enantiomers of PMPDAP was synthesized and evaluated for their biological activity. Compounds containing the combination of guanidino and amino group at the purine moiety enhanced the interferon-gamma-triggered NO production in murine macrophages and stimulated the secretion of cytokines and chemokines in both murine macrophages and human peripheral blood mononuclear cells. The most active compounds are 27 and 54. None of the compounds tested exhibited any significant cytostatic effect or antiviral effect. (C) 2007 Elsevier Ltd. All rights reserved.
• 6-Guanidinopurine nucleosides and their analogues
  作者：Michal Česnek、Antonı́n Holý、Milena Masojı́dková

  DOI：10.1016/s0040-4020(02)00186-2

  日期：2002.4

  A general synthetic approach to 6-guanidinopurines, their ribonucleosides, 2-deoxyribonucleosides, acyclic nucleoside analogues and acyclic nucleoside phosphonates was developed. The approach consists in the reaction of the 6-chloropurine derivatives with guanidine solution in DMF under DABCO catalysis. This method was used to synthesize 6-guanidinopurine and 2-amino-6-guanidinopurine derivatives. Acyclic nucleosides and acyclic nucleoside phosphonates were also obtained by alkylation of the 6-guanidinopurine bases. (C) 2002 Elsevier Science Ltd. All rights reserved.

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