[(3R)-3-[(2-氨基-6-氧代-3H-嘌呤-9-基)甲氧基]-4-羟基丁基]膦酸 | 151006-30-3

• 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: [(3R)-3-[(2-氨基-6-氧代-3H-嘌呤-9-基)甲氧基]-4-羟基丁基]膦酸
• 英文名称: (R)-3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutylphosphonic acid
• 英文别名: <(R)-3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutyl>phosphonic acid；9-[((3R)-1-hydroxymethyl-3-phosphono)propyloxymethyl]guanine；P-[(3R)-3-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-4-hydroxybutyl]-phosphonic acid；(R)-ganciclovir phosphonate；(3-((2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutyl)phosphonic acid；[(3R)-3-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]-4-hydroxybutyl]phosphonic acid
• CAS: 151006-30-3
• 化学式: C₁₀H₁₆N₅O₆P
• 分子量: 333.241
• InChiKey: QVNXYSKNFUJRMI-ZCFIWIBFSA-N

物化性质

• 密度：
  1.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(3R)-3-[(2-氨基-6-氧代-3H-嘌呤-9-基)甲氧基]-4-羟基丁基]膦酸 在 GMP kinase from numan red blood cells 作用下， 生成 (R)-3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutylphosphonic acid monophosphate
  参考文献：
  名称：

  Phosphorylation of Ganciclovir Phosphonate by Cellular GMP Kinase Determines the Stereoselectivity of Anti-Human Cytomegalovirus Activity

  摘要：

  A racemic mixture of ganciclovir phosphonate was resolved by stereoselective phosphorylation using GMP kinase. The R-enantiomer of ganciclovir phosphonate was active against human cytomegalovirus but the S-enantiomer was less active. We show that enantiomeric selectivity of antiviral activity for ganciclovir phosphonate was conferred by stereoselective phosphorylations by mammalian enzymes, not by stereoslective inhibition of DNA polymerase from human cytomegalovirus.

  DOI：

  10.1080/15257770008033013
• 作为产物：
  描述：

  N,9-二乙酰鸟嘌呤 在 苯磺酰胺 、 sodium hydroxide 、 phosphodiesterase 、 三氟甲磺酸三甲基硅酯 、 甲胺 作用下， 反应 2.25h， 生成 [(3R)-3-[(2-氨基-6-氧代-3H-嘌呤-9-基)甲氧基]-4-羟基丁基]膦酸
  参考文献：
  名称：

  An Enantiospecific Synthesis of the Human Cytomegalovirus Antiviral Agent [(R)-3-((2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4- hydroxybutyl]phosphonic Acid

  摘要：

  The racemic isosteric phosphonate of ganciclovir monophosphate (BW2482U89, SR3745, [3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutyl]phosphonic acid, 1) has potent and selective in vitro;activity against human cytomegalovirus. An enantiospecific synthesis of the R-enantiomer of compound 1 starting from L-arabinose was developed. The synthesis involved (1) the preparation of a chiral acyclic moiety, (2) the coupling of the chiral acyclic moiety to diacetylguanine, (3) the introduction; of phosphorus, and (4) the final deprotection. The R-enantiomer, which has stereochemistry analogous to the natural compound GMP, was tested against human cytomegalovirus and had an IC50 Of 1.7 mu M, which was approximately 2-fold more active than the racemic material. Both racemic and chiral compounds were less toxic than ganciclovir to bone marrow progenitor cells in an in vitro assay.

  DOI：

  10.1021/jm00035a018

文献信息

• 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。
• Pharmacologically Active Agents Containing Esterified Phosphonates and Methods for Use Thereof
  申请人：Hostetler Karl Y.

  公开号：US20100273742A1

  公开（公告）日：2010-10-28

  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.

  本发明提供了用于治疗、预防或改善与病毒感染、细胞增殖和骨代谢有关的各种医疗障碍的化合物和组合物。本文提供的化合物是磷酸酯的烷基酯。
• US5532225A
  申请人：——

  公开号：US5532225A

  公开（公告）日：1996-07-02