((2S,3R,5S)-3-(benzoyloxy)-5-(5-fluoro-2-oxo-4-thioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl benzoate | 725259-06-3

• 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: ((2S,3R,5S)-3-(benzoyloxy)-5-(5-fluoro-2-oxo-4-thioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl benzoate
• CAS: 725259-06-3
• 化学式: C₂₃H₁₉FN₂O₆S
• 分子量: 470.478
• InChiKey: NFTCIYHXMNOYPK-QYZOEREBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  99.62
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ((2S,3R,5S)-3-(benzoyloxy)-5-(5-fluoro-2-oxo-4-thioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl benzoate 在 氨 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以87%的产率得到β-L-2'-deoxy-5-fluorocytidine
  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-deoxy-3,5-di-O-benzoyl-β-L-erythro-pentofuranosyl)-5-fluorouracil 在 劳森试剂 作用下， 以 1,2-二氯乙烷 为溶剂， 以92%的产率得到((2S,3R,5S)-3-(benzoyloxy)-5-(5-fluoro-2-oxo-4-thioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl benzoate
  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

• 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.