1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)-5-fluorouracil | 265988-66-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)-5-fluorouracil
• 英文别名: 1-(2-O-Acetyl-3,5-di-O-Benzoyl-beta-L-Xylofuranosyl)-5-Fluorouracil；[(2S,3R,4S,5S)-4-acetyloxy-3-benzoyloxy-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 265988-66-7
• 化学式: C₂₅H₂₁FN₂O₉
• 分子量: 512.448
• InChiKey: MPGPRVGWRXSGFW-IIZPIQPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)-5-fluorouracil 在 4-二甲氨基吡啶 、 三(三甲基硅基)硅烷 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 一水合肼 作用下， 以 1,4-二氧六环 、 吡啶 、 溶剂黄146 、 乙腈 为溶剂， 反应 3.5h， 生成 1-(2-deoxy-3,5-di-O-benzoyl-β-L-threo-pentofuranosyl)-5-fluorouracil
  参考文献：
  名称：

  Stereospecific synthesis and biological evaluations of β-l-pentofuranonucleoside derivatives of 5-fluorouracil and 5-fluorocytosine

  摘要：

  In the search for new chemotherapeutic agents, we have focused our work on the synthesis and the study of several unnatural beta -L-nucleoside analogues. In this paper, we report on the synthesis Of beta -L-pentofuranonucleosides (and their 2 ' -deoxy derivatives) of 5-fluorouracil and their inhibitory effects on the proliferation of several murine and human tumor cells. The corresponding 5-fluorocytosine derivatives were also synthesized and their anti-HIV and anti-HBV activities have been evaluated. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01238-7
• 作为产物：
  描述：

  1,2-di-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranose 、 O,O’-双(三甲基硅烷)-5-氟尿嘧啶 在 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 以11.0 g的产率得到1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)-5-fluorouracil
  参考文献：
  名称：

  Stereospecific synthesis and biological evaluations of β-l-pentofuranonucleoside derivatives of 5-fluorouracil and 5-fluorocytosine

  摘要：

  In the search for new chemotherapeutic agents, we have focused our work on the synthesis and the study of several unnatural beta -L-nucleoside analogues. In this paper, we report on the synthesis Of beta -L-pentofuranonucleosides (and their 2 ' -deoxy derivatives) of 5-fluorouracil and their inhibitory effects on the proliferation of several murine and human tumor cells. The corresponding 5-fluorocytosine derivatives were also synthesized and their anti-HIV and anti-HBV activities have been evaluated. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01238-7

文献信息

• &bgr;-L nucleosides for the treatment of HIV infection
  申请人：Emory University

  公开号：US06407077B1

  公开（公告）日：2002-06-18

  Compounds and pharmaceutical compositions active against HIV are provided, as is a method for the treatment of HIV infection in humans and other host animals is provided comprising administering an effective amount of a &bgr;-L-(2′ or 3′-azido)-2′,3′-dideoxy-5-fluorocytosine of the formula wherein R is H, acyl, monophosphate, diphosphate, or triphosphate, or a stabilized phosphate derivative (to form a stabilized nucleotide prodrug), and R′ is H, acyl, or alkyl.

  本发明提供了对抗HIV的化合物和制药组合物，以及一种治疗人类和其他宿主动物HIV感染的方法，包括给予有效量的β-L-(2'或3'-azido)-2'，3'-二脱氧-5-氟胞嘧啶，其化学式为其中R为H，酰基，单磷酸，二磷酸或三磷酸，或稳定的磷酸衍生物（形成稳定的核苷酸前药），而R'为H，酰基或烷基。
• β-L-2'-deoxy-nucleosides for the treatment of HIV infection
  申请人：Gosselin Gilles

  公开号：US06896900B2

  公开（公告）日：2005-05-24

  Compounds and pharmaceutical compositions active against HIV are provided, as is a method for the treatment of HIV infection in humans and other host animals is provided comprising administering an effective amount of a β-L-(2′ or 3′-azido)-2′,3′-dideoxy-5-fluorocytosine of the formula wherein R is H, acyl, monophosphate, diphosphate, or triphosphate, or a stabilized phosphate derivative (to form a stabilized nucleotide prodrug), and R′ is H, acyl, or alkyl.

  提供了对抗HIV的化合物和药物组合物，以及一种用于治疗人类和其他宿主动物HIV感染的方法，包括给予有效剂量的式中的β-L-(2′或3′-azido)-2′,3′-dideoxy-5-fluorocytosine，其中R为H、酰基、单磷酸、二磷酸或三磷酸，或稳定的磷酸衍生物（形成稳定的核苷酸前药），而R′为H、酰基或烷基。
• Beta-L-2'-deoxy-nucleosides for the treatment of HIV infection
  申请人：The Centre National da la Recherche Scientifique

  公开号：US20030036528A1

  公开（公告）日：2003-02-20

  Compounds and pharmaceutical compositions active against HIV are provided, as is a method for the treatment of HIV infection in humans and other host animals is provided comprising administering an effective amount of a &bgr;-L-(2′ or 3′-azido)-2′,3′-dideoxy-5-fluorocytosine of the formula 1 wherein R is H, acyl, monophosphate, diphosphate, or triphosphate, or a stabilized phosphate derivative (to form a stabilized nucleotide prodrug), and R′ is H, acyl, or alkyl.

  提供了对 HIV 有活性的化合物和药物组合物，以及治疗人类和其他宿主动物 HIV 感染的方法，包括施用有效量的 &bgr;-L-(2′ 或 3′-叠氮)-2′,3′-二脱氧-5-氟胞嘧啶，其式为 1 其中 R 是 H、酰基、单磷酸、二磷酸或三磷酸，或稳定的磷酸衍生物（形成稳定的核苷酸原药），R′是 H、酰基或烷基。
• NUCLEOSIDES WITH ANTI-HEPATITIS B VIRUS ACTIVITY
  申请人：CENTRE NATIONAL DELA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：EP1124839A2

  公开（公告）日：2001-08-22
• BETA-L-2'-DEOXY-NUCLEOSIDES FOR THE TREATMENT OF HIV INFECTION
  申请人：CENTRE NATIONAL DELA RECHERCHE SCIENTIFIQUE

  公开号：EP1124565A1

  公开（公告）日：2001-08-22