[1-[(2-Amino-6-chloropurin-9-yl)methyl]cyclopropyl]methoxymethylphosphonic acid | 1085516-56-8

• 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: [1-[(2-Amino-6-chloropurin-9-yl)methyl]cyclopropyl]methoxymethylphosphonic acid
• 英文别名: [1-[(2-amino-6-chloropurin-9-yl)methyl]cyclopropyl]methoxymethylphosphonic acid
• CAS: 1085516-56-8
• 化学式: C₁₁H₁₅ClN₅O₄P
• 分子量: 347.698
• InChiKey: NKILLFVGWNIREJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [1-[(2-Amino-6-chloropurin-9-yl)methyl]cyclopropyl]methoxymethylphosphonic acid 在 盐酸 作用下， 反应 7.0h， 以75%的产率得到((1-((2-amino-6-oxo-1,6-dihydropurin-9-yl)methyl)cyclopropyl)methoxy)methylphosphonic acid
  参考文献：
  名称：

  Design, Synthesis and Anti-HIV Activity of Homologous PMEA Derivatives

  摘要：

  This article describes an efficient route for synthesizing novel cyclopropyl homologous PMEA analogues. The condensation of the bromide 8 with nucleosidic bases (A, U, T, C, 5-FU, G) under standard nucleophilic substitution and deprotection conditions, afforded the target phosphonic acid analogues 14 similar to 18 and 21. These compounds were evaluated for their potential antiviral properties against various viruses. Guanine derivative 21 showed significant antiviral activity.

  DOI：

  10.1080/15257770701795953
• 作为产物：
  描述：

  9-[1-(diisopropoxyphosphorylmethoxymethyl)cyclopropylmethyl]-2-amino-6-chloropurine 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到[1-[(2-Amino-6-chloropurin-9-yl)methyl]cyclopropyl]methoxymethylphosphonic acid
  参考文献：
  名称：

  Design, Synthesis and Anti-HIV Activity of Homologous PMEA Derivatives

  摘要：

  This article describes an efficient route for synthesizing novel cyclopropyl homologous PMEA analogues. The condensation of the bromide 8 with nucleosidic bases (A, U, T, C, 5-FU, G) under standard nucleophilic substitution and deprotection conditions, afforded the target phosphonic acid analogues 14 similar to 18 and 21. These compounds were evaluated for their potential antiviral properties against various viruses. Guanine derivative 21 showed significant antiviral activity.

  DOI：

  10.1080/15257770701795953

文献信息

• Nucleobase phosphonate analogs for antiviral treatment
  申请人：Krawczyk H. Steven

  公开号：US20050059637A1

  公开（公告）日：2005-03-17

  The present invention provides novel compounds with activity against infectious viruses. The compounds of the invention may inhibit retroviral reverse transcriptases and thus inhibit the replication of the virus. They are useful for treating human patients infected with a human retrovirus, such as human immunodeficiency virus (strains of HIV-1 or HIV-2) or human T-cell leukemia viruses (HTLV-I or HTLV-II) which results in acquired immunodeficiency syndrome (AIDS) and/or related diseases. The present invention also relates generally to the accumulation or retention of therapeutic compounds inside cells. The invention is more particularly related to attaining high concentrations of active metabolite molecules in HIV infected cells. Intracellular targeting may be achieved by methods and compositions which allow accumulation or retention of biologically active agents inside cells. Such effective targeting may be applicable to a variety of therapeutic formulations and procedures.

  本发明提供了一种对抗传染病毒的新化合物。本发明的化合物可以抑制逆转录病毒逆转录酶，从而抑制病毒的复制。它们可用于治疗感染人类逆转录病毒（如HIV-1或HIV-2的菌株）或人类T细胞白血病病毒（HTLV-I或HTLV-II）而导致获得性免疫缺陷综合症（AIDS）和/或相关疾病的人类患者。本发明还涉及治疗化合物在细胞内的积累或保留。本发明更具体地涉及在感染HIV的细胞中获得活性代谢物分子的高浓度。通过允许生物活性剂在细胞内积累或保留的方法和组合物可以实现细胞内靶向。这种有效的靶向可以适用于各种治疗配方和程序。
• US7579332B2
  申请人：——

  公开号：US7579332B2

  公开（公告）日：2009-08-25
• Design, Synthesis and Anti-HIV Activity of Homologous PMEA Derivatives
  作者：Chang Hyun Oh、Joon Hee Hong

  DOI：10.1080/15257770701795953

  日期：2008.1.18

  This article describes an efficient route for synthesizing novel cyclopropyl homologous PMEA analogues. The condensation of the bromide 8 with nucleosidic bases (A, U, T, C, 5-FU, G) under standard nucleophilic substitution and deprotection conditions, afforded the target phosphonic acid analogues 14 similar to 18 and 21. These compounds were evaluated for their potential antiviral properties against various viruses. Guanine derivative 21 showed significant antiviral activity.