9-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)adenine | 154463-68-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)adenine
• 英文别名: 9-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylo-furanosyl)adenine；9-(2-O-acetyl-3,5-di-O-benzoyl-beta-L-xylofuranosyl)adenine；[(2S,3R,4S,5S)-4-acetyloxy-5-(6-aminopurin-9-yl)-3-benzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 154463-68-0
• 化学式: C₂₆H₂₃N₅O₇
• 分子量: 517.498
• InChiKey: FQVCSCHSSVDBKM-UQWVPHONSA-N

物化性质

• 沸点：
  725.9±70.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  9-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)adenine 在 4-二甲氨基吡啶 、 三氟甲磺酸酐 、 四丁基氟化铵 、 氨 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 生成 L-adenosine
  参考文献：
  名称：

  A New and Convenient Approach for the Synthesis of Ribo- and 2′-Deoxyribo-β-L-Furanonucleosides Starting From β-L-Xylofuranonucleosides

  摘要：

  Ribo- and 2'-deoxyribo-beta-L-furanosyladenine have been synthesized. Although these compounds have been already reported in the literature, it seemed to us that a more convenient approach for their synthesis deserved to be developed. Intramolecular substitution as well as Mitsunobu reaction were used to invert the configuration of carbon 3' of starting beta-L-xylofuranosyl intermediates.

  DOI：

  10.1080/15257779908041512
• 作为产物：
  描述：

  5,7-二氢-4H-嘌呤-6-胺 、 1,2-di-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranose 在 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以61%的产率得到9-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)adenine
  参考文献：
  名称：

  合成和β-L-的抗病毒评价低聚木糖五个-fuanosyl核苷天然存在的核酸碱基†

  摘要：

  已经合成了天然存在的核苷的β-L-二甲苯基-呋喃糖基类似物，并研究了它们的抗病毒特性。迄今为止，所有这些化合物都是未知的，它们是通过嘧啶和嘌呤糖苷配基与合适的过酰基-L-木糖-呋喃糖（为达到我们目前的目的特别从L-木糖合成）进行糖基化立体定向制备的，然后除去保护基团。测试了所有制备的化合物对多种DNA和RNA病毒（包括HIV）的活性，但它们未显示出显着的抗病毒活性。

  DOI：

  10.1002/jhet.5570300510

文献信息

• Methods of treating hepatitis delta virus infection with beta-l-2'-deoxy-nucleosides
  申请人：——

  公开号：US20020035085A1

  公开（公告）日：2002-03-21

  A method and composition for treating a host infected with hepatitis D comprising administering an effective hepatitis D treatment amount of a described 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof.

  一种治疗感染乙型肝炎的宿主的方法和组合物，包括给予所述2'-脱氧-β-L-赤霉糖核苷或其药用可接受的盐或前药的有效乙型肝炎治疗剂量。
• &bgr;-L-2'-deoxy-nucleosides for the treatment of hepatitis B
  申请人：Novirio Pharmaceuticals Limited

  公开号：US06444652B1

  公开（公告）日：2002-09-03

  This invention is directed to a method for treating a host infected with hepatitis B comprising administering an effective amount of an anti-HBV biologically active 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof, wherein the 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside has the formula: wherein R is selected from the group consisting of H, straight chained, branched or cyclic alkyl, CO-alkyl, CO-aryl, CO-alkoxyalkyl, CO-aryloxyalkyl, CO-substituted aryl, alkylsulfonyl, arylsulfonyl, aralkylsulfonyl, amino acid residue, mono, di, or triphosphate, or a phosphate derivative; and BASE is a purine or pyrimidine base which may be optionally substituted. The 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof may be administered either alone or in combination with another 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or in combination with another anti-hepatitis B agent.

  本发明涉及一种治疗乙型肝炎感染宿主的方法，包括给予有效量的抗HBV生物活性2'-脱氧-β-L-核糖呋喃核苷或其药物可接受的盐或前药，其中2'-脱氧-β-L-核糖呋喃核苷的化学式为：其中R选自H、直链、支链或环烷基、CO-烷基、CO-芳基、CO-烷氧基烷基、CO-芳氧基烷基、CO-取代芳基、烷基磺酰基、芳基磺酰基、芳基烷基磺酰基、氨基酸残基、单、二或三磷酸盐或磷酸衍生物；BASE是一种可以选择性取代的嘌呤或嘧啶碱基。2'-脱氧-β-L-核糖呋喃核苷或其药物可接受的盐或前药可以单独或与另一种2'-脱氧-β-L-核糖呋喃核苷或其他抗乙型肝炎药物联合使用。
• &bgr;-L-2′-deoxy-nucleosides for the treatment of hepatitis B
  申请人：Novirio Pharmaceuticals Limited

  公开号：US06395716B1

  公开（公告）日：2002-05-28

  This invention is directed to a method for treating a host infected with hepatitis B comprising administering an effective amount of an anti-HBV biologically active 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof, wherein the 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside has the formula: wherein R is selected from the group consisting of H, straight chained, branched or cyclic alkyl, CO-alkyl, CO-aryl, CO-alkoxyalkyl, CO-aryloxyalkyl, CO-substituted aryl, alkylsulfonyl, arylsulfonyl, aralkylsulfonyl, amino acid residue, mono, di, or triphosphate, or a phosphate derivative; and BASE is a purine or pyrimidine base which may be optionally substituted. The 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof may be administered either alone or in combination with another 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or in combination with another anti-hepatitis B agent.

  本发明涉及一种治疗乙型肝炎感染宿主的方法，包括给予有效量的抗HBV生物活性2'-去氧-β-L-赤霉糖核苷或其药物可接受的盐或前药，其中2'-去氧-β-L-赤霉糖核苷的化学式为：其中R选自H、直链、支链或环烷基、CO-烷基、CO-芳基、CO-烷氧基烷基、CO-芳氧基烷基、CO-取代芳基、烷基磺酰基、芳基磺酰基、芳基烷基磺酰基、氨基酸残基、单、二或三磷酸盐或磷酸衍生物；BASE为一种可以选择性地取代的嘌呤或嘧啶碱基。2'-去氧-β-L-赤霉糖核苷或其药物可接受的盐或前药可以单独或与另一种2'-去氧-β-L-赤霉糖核苷或另一种抗乙型肝炎药物联合使用。
• [EN] beta -L-2'-DEOXY-NUCLEOSIDES FOR THE TREATMENT OF HEPATITIS B<br/>[FR] beta -L-2'-DESOXY-NUCLEOSIDES POUR LE TRAITEMENT DE L'HEPATITE B
  申请人：NORIVIO PHARMACEUTICALS LTD

  公开号：WO2000009531A2

  公开（公告）日：2000-02-24

  This invention is directed to a method for treating a host infected with hepatitis B comprising administering an effective amount of an anti-HBV biologically active 2'-deoxy-β-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof, wherein the 2'-deoxy-β-L-erythro-pentofuranonucleoside has formula (I) wherein R is selected from the group consisting of H, straight chained, branched or cyclic alkyl, CO-alkyl, CO-aryl, CO-alkoxyalkyl, CO-aryloxyalkyl, CO-substituted aryl, alkylsulfonyl, arylsulfonyl, aralkylsulfonyl, amino acid residue, mono, di, or triphosphate, or a phosphate derivative; and BASE is a purine or pyrimidine base which may be optionally substituted. The 2'-deoxy-β-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof may be administered either alone or in combination with another 2'-deoxy-β-L-erythro-pentofuranonucleoside or in combination with another anti-hepatitis B agent.

  本发明涉及一种治疗乙型肝炎感染宿主的方法，包括给予有效量的抗HBV生物活性2'-脱氧-β-L-erythro-戊糖核苷或其药学上可接受的盐或前药，其中2'-脱氧-β-L-erythro-戊糖核苷具有式(I)，其中R选自H、直链、支链或环烷基、CO-烷基、CO-芳基、CO-烷氧基烷基、CO-芳氧基烷基、CO-取代芳基、烷基磺酰基、芳基磺酰基、芳基烷基磺酰基、氨基酸残基、单磷酸、二磷酸或三磷酸或磷酸衍生物；而基团是一种可以选择性地被取代的嘌呤或嘧啶碱基。2'-脱氧-β-L-erythro-戊糖核苷或其药学上可接受的盐或前药可以单独给予或与另一种2'-脱氧-β-L-erythro-戊糖核苷或另一种抗乙型肝炎药物联合给予。
• Beta-L-2'-deoxy-nucleosides for the treatment of hepatitis B
  申请人：Centre National da la Reserche Scientifique

  公开号：US20030220290A1

  公开（公告）日：2003-11-27

  This invention is directed to a method for treating a host infected with hepatitis B comprising administering an effective amount of an anti-HBV biologically active 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof, wherein the 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside has the formula: 1 wherein R is selected from the group consisting of H, straight chained, branched or cyclic alkyl, CO-alkyl, CO-aryl, CO-alkoxyalkyl, CO-aryloxyalkyl, CO-substituted aryl, alkylsulfonyl, arylsulfonyl, aralkylsulfonyl, amino acid residue, mono, di, or triphosphate, or a phosphate derivative; and BASE is a purine or pyrimidine base which may be optionally substituted. The 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof may be administered either alone or in combination with another 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or in combination with another anti-hepatitis B agent.

  本发明涉及一种治疗乙型肝炎感染宿主的方法，包括给予一种抗HBV生物活性2'-脱氧-β-L-核糖呋喃核苷或其药学上可接受的盐或前药的有效量，其中2'-脱氧-β-L-核糖呋喃核苷的化学式为：1，其中R选自H、直链、支链或环烷基、CO-烷基、CO-芳基、CO-烷氧基烷基、CO-芳氧基烷基、CO-取代芳基、烷基磺酰基、芳基磺酰基、芳基烷基磺酰基、氨基酸残基、单、二或三磷酸盐或磷酸衍生物；BASE是嘌呤或嘧啶碱基，可以选择性地被取代。2'-脱氧-β-L-核糖呋喃核苷或其药学上可接受的盐或前药可以单独使用或与另一种2'-脱氧-β-L-核糖呋喃核苷或另一种抗乙型肝炎药物联合使用。