(2S)-ethyl 2-(((((2R,4R)-4-(2-amino-6-hydroxy-9H-purin-9-yl)-1,3-dioxolan-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate | 1239439-31-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-ethyl 2-(((((2R,4R)-4-(2-amino-6-hydroxy-9H-purin-9-yl)-1,3-dioxolan-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
• 英文别名: ethyl (2S)-2-[[[(2R,4R)-4-(2,6-diaminopurin-9-yl)-1,3-dioxolan-2-yl]methoxy-phenoxy-phosphoryl]amino]propanoate；ethyl (2S)-2-[[[(2R,4R)-4-(2,6-diaminopurin-9-yl)-1,3-dioxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
• CAS: 1239439-31-6
• 化学式: C₂₀H₂₆N₇O₇P
• 分子量: 507.443
• InChiKey: YFYHWNLDSMAGMI-DBCIDPAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  188
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  (2R,4R)-4-(2,6-二氨基-9H-嘌呤-9-基)-1,3-二氧戊环-2-甲醇 、 (2S)-2-((氯(苯氧基)膦)氨基)丙酸乙酯 在 叔丁基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以45%的产率得到(2S)-ethyl 2-(((((2R,4R)-4-(2-amino-6-hydroxy-9H-purin-9-yl)-1,3-dioxolan-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
  参考文献：
  名称：

  Synthesis and antiviral evaluation of 2-amino-6-carbamoylpurine dioxolane nucleoside derivatives and their phosphoramidates prodrugs

  摘要：

  The synthesis of 9-(beta-D-1,3-dioxolan-4-yl)2,6-diaminopurine nucleoside phosphoramidate prodrugs as well as various 2-amino-6-carbamoylpurine dioxolane derivatives and their phosphoramidates prodrugs is reported. Their ability to block HIV and HBV replication along with their cytotoxicity toward HepG2, human lymphocyte, CEM and Vero cells was also assessed. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.10.003

文献信息

• MONOPHOSPHATE PRODRUGS OF DAPD AND ANALOGS THEREOF
  申请人：Schinazi Raymond F.

  公开号：US20120142627A1

  公开（公告）日：2012-06-07

  The present invention is directed to compounds, compositions and methods for treating or preventing cancer and viral infections, in particular, HIV and HBV, in human patients or other animal hosts. The compounds are certain 6-substituted-2-amino-purine dioxolane monophosphates or phosphonates, and pharmaceutically acceptable, salts, prodrugs, and other derivatives thereof.

  本发明涉及用于治疗或预防癌症和病毒感染，特别是HIV和HBV，在人类患者或其他动物宿主中的化合物、组合物和方法。这些化合物是某些6-取代-2-氨基嘧啶二氧杂环己糖单磷酸盐或膦酸盐，以及其药用可接受的盐、前药和其他衍生物。
• PURINE NUCLEOSIDE MONOPHOSPHATE PRODRUGS FOR TREATMENT OF CANCER AND VIRAL INFECTIONS
  申请人：Cho Jong Hyun

  公开号：US20120040924A1

  公开（公告）日：2012-02-16

  The present invention is directed to compounds, compositions and methods for treating or preventing cancer and viral infections, in particular, HIV, HCV, Norovirus, Saporovirus, HSV-1, HSV-2, Dengue virus, Yellow fever, and HBV in human patients or other animal hosts. The compounds are certain 6-substituted purine monophosphates, and pharmaceutically acceptable, salts, prodrugs, and other derivatives thereof. In particular, the compounds show potent antiviral activity against HIV-1, HIV-2, HCV, Norovirus, Saporovirus, HSV-1, HSV-2, Dengue virus, Yellow fever, and HBV.

  本发明涉及化合物、组合物和方法，用于治疗或预防癌症和病毒感染，特别是在人类患者或其他动物宿主中的HIV、HCV、Norovirus、Saporovirus、HSV-1、HSV-2、登革热病毒、黄热病和HBV。这些化合物是某些6-取代嘌呤单磷酸盐，以及其药学上可接受的盐、前药和其他衍生物。特别是这些化合物显示出对HIV-1、HIV-2、HCV、Norovirus、Saporovirus、HSV-1、HSV-2、登革热病毒、黄热病和HBV的强效抗病毒活性。
• US9173893B2
  申请人：——

  公开号：US9173893B2

  公开（公告）日：2015-11-03
• Synthesis and antiviral evaluation of 2-amino-6-carbamoylpurine dioxolane nucleoside derivatives and their phosphoramidates prodrugs
  作者：Jong Hyun Cho、Lavanya Bondana、Mervi A. Detorio、Cathy Montero、Leda C. Bassit、Franck Amblard、Steven J. Coats、Raymond F. Schinazi

  DOI：10.1016/j.bmc.2014.10.003

  日期：2014.12

  The synthesis of 9-(beta-D-1,3-dioxolan-4-yl)2,6-diaminopurine nucleoside phosphoramidate prodrugs as well as various 2-amino-6-carbamoylpurine dioxolane derivatives and their phosphoramidates prodrugs is reported. Their ability to block HIV and HBV replication along with their cytotoxicity toward HepG2, human lymphocyte, CEM and Vero cells was also assessed. Published by Elsevier Ltd.