α-5-Fluordesoxyuridin-5'-carbonsaeure | 55774-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: α-5-Fluordesoxyuridin-5'-carbonsaeure
• 英文别名: 1-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-α-D-erythro-1,2-dideoxy-pentofuranuronic acid
• CAS: 55774-29-3
• 化学式: C₉H₉FN₂O₆
• 分子量: 260.179
• InChiKey: OHKLEIJCOJXRTB-ZLUOBGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.59
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  121.62
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 α-5-Fluordesoxyuridin-5'-carbonsaeure 在 吡啶 作用下， 反应 73.0h， 以43%的产率得到1-(3-O-acetyl-2-deoxy-β-d-erythro-pentofuranosyl-4-carboxy)-5-fluorouracil
  参考文献：
  名称：

  A new class of pyrimidine nucleosides: inhibitors of hepatitis B and C viruses

  摘要：

  Hepatitis B virus (HBV) and hepatitis C virus (HCV) infections are major health threats worldwide leading to liver cirrhosis, liver cancer and mortality. Herein, we report a new category of dideoxy pyrimidine nucleosides possessing a 4'-carboxyl (or carboxymethyl) function (7-9, 13, 16, 17), which are discovered as potential antiviral agents. For the first time, these nucleosides are recognized to be inhibitors of HBV and/or HCV replication. Among 4'-carboxy compounds, 3',4'-didehydrothymidine (16) was most effective against DHBV, HBV and HCV. Modification of the 4'-position in compound 7 from a carboxyl to carboxymethyl group (17) did not affect the anti-HBV activity but greatly increased the anti-HCV activity. Importantly, 17 yielded synergistic antiviral effect when combined with ribavirin without toxicity. The activity exhibited by a single agent towards both hepatitis viruses and no detectable in vitro cytotoxicity make this new class of compounds of interest. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.042
• 作为产物：
  描述：

  α-2'-deoxy-5-fluorouridine 在 水合三氯化钌 、 potassium persulfate 、 potassium hydroxide 作用下， 反应 5.0h， 以31%的产率得到α-5-Fluordesoxyuridin-5'-carbonsaeure
  参考文献：
  名称：

  A new class of pyrimidine nucleosides: inhibitors of hepatitis B and C viruses

  摘要：

  Hepatitis B virus (HBV) and hepatitis C virus (HCV) infections are major health threats worldwide leading to liver cirrhosis, liver cancer and mortality. Herein, we report a new category of dideoxy pyrimidine nucleosides possessing a 4'-carboxyl (or carboxymethyl) function (7-9, 13, 16, 17), which are discovered as potential antiviral agents. For the first time, these nucleosides are recognized to be inhibitors of HBV and/or HCV replication. Among 4'-carboxy compounds, 3',4'-didehydrothymidine (16) was most effective against DHBV, HBV and HCV. Modification of the 4'-position in compound 7 from a carboxyl to carboxymethyl group (17) did not affect the anti-HBV activity but greatly increased the anti-HCV activity. Importantly, 17 yielded synergistic antiviral effect when combined with ribavirin without toxicity. The activity exhibited by a single agent towards both hepatitis viruses and no detectable in vitro cytotoxicity make this new class of compounds of interest. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.042