(S)-6-guanidino-7-[2-(phosphonomethoxy)propyl]-7H-purine | 1016647-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (S)-6-guanidino-7-[2-(phosphonomethoxy)propyl]-7H-purine
• 英文别名: [(2S)-1-[6-(diaminomethylideneamino)purin-7-yl]propan-2-yl]oxymethylphosphonic acid
• CAS: 1016647-30-5
• 化学式: C₁₀H₁₆N₇O₄P
• 分子量: 329.255
• InChiKey: USBXDYZHJNKAFO-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  175
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (S)-7-{2-[(diisopropoxyphosphoryl)methoxy]propyl}-6-guanidino-7H-purine 在 三甲基溴硅烷 、 氨 作用下， 以 乙腈 、 水 为溶剂， 反应 0.08h， 以48%的产率得到(S)-6-guanidino-7-[2-(phosphonomethoxy)propyl]-7H-purine
  参考文献：
  名称：

  Synthesis of guanidino analogues of PMPDAP and their immunobiological activity

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.10.010

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.