3',5'-dideoxythymidin-2'-ene-5'-phosphonic acid

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3',5'-dideoxythymidin-2'-ene-5'-phosphonic acid
• 英文别名: [(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methylphosphonic acid；[(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methylphosphonic acid
• 化学式: C₁₀H₁₃N₂O₆P
• 分子量: 288.197
• InChiKey: MLXJMXIPJFZZQG-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-<5'-deoxy-5'-(dimethylphosphono)-β-D-threo-pentofuranosyl>thymine 在 吡啶 、 4-二甲氨基吡啶 、 三甲基溴硅烷 、 锂丁酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 3',5'-dideoxythymidin-2'-ene-5'-phosphonic acid
  参考文献：
  名称：

  Design, Synthesis, and Structure-Activity Relationship of Novel Dinucleotide Analogs as Agents against Herpes and Human Immunodeficiency Viruses

  摘要：

  A new acyclic nucleoside phosphonate (13) containing an adenine moiety was synthesized, which acted as an excellent inhibitor of calf mucosal adenosine deaminase. This inhibitory property allows it to exert great synergistic effect on certain antiviral agents (e.g., ara-A, 37). Phosphonate 13 was not phosphorylated by the bovine brain guanylate kinase nor by 5-phosphoribosyl 1-pyrophosphate synthetase. Syntheses of biologically active nucleotide phosphonate 40 and its phosphonoamidate derivative 42 were accomplished, which showed remarkable activity against herpes viruses and exhibited low host cell toxicity. 3'-Azido-nucleoside phosphonate 20 and 3'-fluoronucleoside phosphonate 32, as well as the corresponding dinucleotide analogs 47 and 48, and their respective phosphonoamidates 53-56 were also synthesized as new compounds, among which phosphonoamidates 53-56 showed potent activity against human immunodeficiency virus. Phosphonoamidates 55 and 56 bearing a methyl D-alaninate moiety exhibited less cellular toxicity than 53 and 54 bearing a methyl L-alaninate moiety. Nucleotide phosphonate 40 as well as dinucleotide phosphonates 47 and 48 were found susceptible to degradation by phosphodiesterases. Their respective phosphonoamidates 42 and 53-56, however, were completely resistant to snake venom and spleen enzymes.

  DOI：

  10.1021/jm00023a004

文献信息

• Pharmacologically active agents containing esterified phosphonates and methods for use thereof
  申请人：Hostetler Y. Karl

  公开号：US20050192246A1

  公开（公告）日：2005-09-01

  Compounds and compositions are provided for treatment, prevention, or amelioration of a variety of medical disorders associated with viral infections, cell proliferation and bone metabolism. The compounds provided herein are alkyl esters of phosphonates.

  提供了用于治疗、预防或改善与病毒感染、细胞增殖和骨代谢相关的各种医学疾病的化合物和组合物。本文提供的化合物是磷酸酯的烷基酯。
• [EN] PHOSPHONATE COMPOUNDS<br/>[FR] COMPOSES DE PHOSPHONATE
  申请人：UNIV CALIFORNIA SAN DIEGO

  公开号：WO2001039724A2

  公开（公告）日：2001-06-07

  The present invention relates to phosphonate compounds, compositions containing them, processes for obtaining them, and their use for treating a variety of medical disorders, e.g., osteoporosis and other disorders of bone metabolism, cancer, viral infections, and the like.

  本发明涉及膦酸酯化合物、包含其的组合物、制备它们的过程以及它们用于治疗各种医学紊乱，例如骨质疏松症和其他骨代谢紊乱、癌症、病毒感染等。
• PHOSPHONATE COMPOUNDS
  申请人：Hostetler Y. Karl

  公开号：US20080103115A1

  公开（公告）日：2008-05-01

  The present invention relates to phosphonate compounds, compositions containing them, processes for obtaining them, and their use for treating a variety of medical disorders, e.g., osteoporosis and other disorders of bone metabolism, cancer, viral infections, and the like.

  本发明涉及磷酸酯化合物、含有它们的组合物、制备它们的方法以及它们用于治疗各种医学疾病，例如骨质疏松症和其他骨代谢紊乱、癌症、病毒感染等。
• Phosphonate compounds
  申请人：Hostetler Y. Karl

  公开号：US20070161602A1

  公开（公告）日：2007-07-12

  The present invention relates to phosphonate compounds, compositions containing them, processes for obtaining them, and their use for treating a variety of medical disorders, e.g., osteoporosis and other disorders of bone metabolism, cancer, viral infections, and the like.

  本发明涉及膦酸盐化合物、含有它们的组合物、获得它们的过程及其用于治疗多种医学疾病的用途，例如骨质疏松症和其他骨代谢紊乱、癌症、病毒感染等。
• Phosphonate Compounds
  申请人：Hostetler Karl Y.

  公开号：US20100173870A1

  公开（公告）日：2010-07-08

  The present invention relates to phosphonate compounds, compositions containing them, processes for obtaining them, and their use for treating a variety of medical disorders, e.g., osteoporosis and other disorders of bone metabolism, cancer, viral infections, and the like.

  本发明涉及磷酸酯化合物、含有它们的组合物、获得它们的过程以及将它们用于治疗各种医学疾病的用途，例如骨质疏松症和其他骨代谢障碍、癌症、病毒感染等。