1-(2-deoxy-3,5-di-O-benzoyl-β-L-threo-pentofuranosyl)-5-fluorouracil | 77180-89-3

• 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-deoxy-3,5-di-O-benzoyl-β-L-threo-pentofuranosyl)-5-fluorouracil
• 英文别名: 1-(3,5-di-O-benzoyl-2-deoxy-beta-L-xylofuranosyl)-5-fluorouracil；[(2S,3S,5S)-3-benzoyloxy-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 77180-89-3
• 化学式: C₂₃H₁₉FN₂O₇
• 分子量: 454.411
• InChiKey: QSWJDRDXNLNCJA-FHWLQOOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-3,5-di-O-benzoyl-β-L-threo-pentofuranosyl)-5-fluorouracil 在 氨 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-(2-deoxy-3,5-di-O-benzoyl-β-L-erythro-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-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

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。
• [EN] 2' OR 3'-DEOXY AND 2'-DIDEOXY- beta -L-PENTAFURANONUCLEOSIDE COMPOUNDS, METHOD OF PREPARATION AND APPLICATION IN THERARY, ESPECIALLY AS ANTI-VIRAL AGENTS<br/>[FR] COMPOSES 2' OU 3'-DEOXY- ET 2', 3'-DIDEOXY- beta -L-PENTOFURANONUCLEOSIDES, PROCEDE DE PREPARATION ET APPLICATION THERAPEUTIQUE, NOTAMMENT ANTI-VIRALE
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：WO1995007287A1

  公开（公告）日：1995-03-16

  (EN) Method for the stereospecific preparation of 2' or 3' deoxy and 2', 3'-dideoxy-$g(b)-L-pentafuanonucleoside compounds. 2' or 3' deoxy and 2', 3'-dideoxy-$g(b)-L-pentofuranonucleoside compounds are also described. Finally, the invention concerns the use of these compounds, and particularly 2', 3' dideoxy-$g(b)-L-5-fluorocytidine, as drugs, and especially as anti-viral agents.(FR) La présente invention a pour objet un procédé de préparation stéréospécifique de composés 2' ou 3' déoxy et 2', 3'-didéoxy-$g(b)-L-pentofuranonucléosides. La présente invention concerne également des composés 2' ou 3' déoxy et 2', 3' didéoxy-$g(b)-L-pentofuranonucléosides. La présente invention concerne enfin l'utilisation de ces composés et notamment de 2', 3'-didéoxy-$g(b)-L-5-fluoro-cytidine à titre de médicaments et notamment à titre d'agents anti-viraux.

  (中) 本发明涉及一种立体特异性制备2'或3'去氧和2'，3'-二去氧-$g(b)-L-戊糖核苷化合物的方法。本发明还涉及2'或3'去氧和2'，3'-二去氧-$g(b)-L-戊糖核苷化合物。最后，本发明涉及这些化合物的用途，特别是2'，3'二去氧-$g(b)-L-5-氟胞嘧啶作为药物，特别是作为抗病毒剂。
• 2' or 3' -deoxy and 2' , 3' -dideoxy-beta-L-pentofuranonucleo-side compounds, method of preparation and application in therapy, especially as anti-viral agents
  申请人：Gosselin Gilles

  公开号：US20050101776A1

  公开（公告）日：2005-05-12

  Method for the sterospecific preparation of 2′ or 3′ deoxy and 2′,3′-dideoxy-β-L-pentafuranonucleoside compounds. 2′ or 3′ deoxy and 2′,3′-dideoxy-β-L-pentofuranonucleoside compounds are also described. Finally, the invention concerns the use of these compounds, and particularly 2′,3′dideoxy-β-L-fluorocytidine, as drugs, and especially as anti-viral agents.

  一种立体选择性制备2′或3′去氧和2′,3′-二去氧-β-L-戊糖核苷化合物的方法。还描述了2′或3′去氧和2′,3′-二去氧-β-L-戊糖核苷化合物。最后，本发明涉及这些化合物的用途，特别是2′,3′-二去氧-β-L-氟胞嘧啶作为药物，特别是作为抗病毒剂。
• 2' or 3' -deoxy and 2', 3' -dideoxy-beta-L-pentofuranonucleo-side compounds, method of preparation and application in therapy, especially as anti- viral agents
  申请人：——

  公开号：US20020120130A1

  公开（公告）日：2002-08-29

  Method for the sterospecific preparation of 2′ or 3′ deoxy and 2′, 3′-dideoxy-&bgr;-L-pentofuranonucleoside compounds. 2′ or 3′ deoxy and 2′, 3′-dideoxy-&bgr;-L-pentofuranonucleoside compounds are also described. Finally, the invention concerns the use of these compounds, and particularly 2′, 3′ dideoxy-&bgr;-L-fluorocytidine, as drugs, and especially as anti-viral agents.

  这是一种用于立体选择性制备2'或3'脱氧和2'，3'-二脱氧-β-L-戊糖呋喃核苷化合物的方法。本发明还描述了2'或3'脱氧和2'，3'-二脱氧-β-L-戊糖呋喃核苷化合物。最后，本发明涉及这些化合物的用途，特别是2'，3'二脱氧-β-L-氟胞嘧啶作为药物，特别是作为抗病毒药物。
• 2′ or 3′ -deoxy and 2′, 3′-dideoxy-β-L-pentofuranonucleo-side compounds, method of preparation and application in therapy, especially as anti-viral agents
  申请人：The UAB Research Foundation

  公开号：US07439351B2

  公开（公告）日：2008-10-21

  Method for the sterospecific preparation of 2′ or 3′ deoxy and 2′,3′-dideoxy-β-L-pentafuranonucleoside compounds. 2′ or 3′ deoxy and 2′,3′-dideoxy-β-L-pentofuranonucleoside compounds are also described. Finally, the invention concerns the use of these compounds, and particularly 2′,3′dideoxy-β-L-fluorocytidine, as drugs, and especially as anti-viral agents.

  2′或3′去氧和2′,3′-二去氧-β-L-戊糖核苷化合物的立体特异性制备方法。还描述了2′或3′去氧和2′,3′-二去氧-β-L-戊糖核苷化合物。最后，本发明涉及这些化合物的用途，特别是2′,3′-二去氧-β-L-氟胞嘧啶作为药物，特别是作为抗病毒剂。