1-(2-deoxy-β-L-threo-pentofuranosyl)-5-fluorouracil | 169527-98-4

• 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-β-L-threo-pentofuranosyl)-5-fluorouracil
• 英文别名: 1-(2-Deoxy-beta-L-threo-pentofuranosyl)-5-fluorouracil；5-fluoro-1-[(2S,4S,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 169527-98-4
• 化学式: C₉H₁₁FN₂O₅
• 分子量: 246.195
• InChiKey: ODKNJVUHOIMIIZ-ACZMJKKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-β-L-threo-pentofuranosyl)-5-fluorouracil 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 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-(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 、 氨 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 3.5h， 生成 1-(2-deoxy-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

• 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。
• US7439351B2
  申请人：——

  公开号：US7439351B2

  公开（公告）日：2008-10-21
• Stereospecific synthesis and biological evaluations of β-l-pentofuranonucleoside derivatives of 5-fluorouracil and 5-fluorocytosine
  作者：Jean-François Griffon、Christophe Mathé、Abdesslem Faraj、Anne-Marie Aubertin、Erik De Clercq、Jan Balzarini、Jean-Pierre Sommadossi、Gilles Gosselin

  DOI：10.1016/s0223-5234(01)01238-7

  日期：2001.5

  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.