5-[bis(2,2,2-trifluoroethoxy)methyl]-3'-fluoro-2',3'-dideoxyuridine

• 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: 5-[bis(2,2,2-trifluoroethoxy)methyl]-3'-fluoro-2',3'-dideoxyuridine
• 英文别名: 5-[bis(2,2,2-trifluoroethoxy)methyl]-1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione；5-[bis(2,2,2-trifluoroethoxy)methyl]-1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• 化学式: C₁₄H₁₅F₇N₂O₆
• 分子量: 440.272
• InChiKey: VTZTVWMJOAQPBD-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  3’-脱氧-3-氟胸苷 在 吡啶 、 四丁基氟化铵 、 溴 作用下， 以 甲醇 、 四氯化碳 、 乙二醇二甲醚 为溶剂， 反应 0.75h， 生成 5-[bis(2,2,2-trifluoroethoxy)methyl]-3'-fluoro-2',3'-dideoxyuridine
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Novel Fluorinated 2′,3′‐Dideoxynucleosides

  摘要：

  A series of 5-(trifluoroethoxymethyl)-2',3'-dideoxyuridines and 5-[bis(trifluorroethoxy)-methyl]-2', 3'-dideoxyuri dines have been prepared and screened for antiviral activity. The conformations of these compounds are discussed on the bases of NOE studies and the MO calculations. Modelling and NOE studies suggest both syn- and anti conformations for these 5-(2,2,2-trifluoroethoxymethyl)- and 5-[bis(2,2,2-trifluoroethoxy)-methyl]- derivatives. The NOE parameters are also suggested to be more attributable to the nature of the fluorine atom than to structural or conformational changes. Compounds 17, 26 and 30 showed some activity in anti-HIV-1 and anti-HIV-2 assays, but the compounds were devoid of activity against HSV and human rhinovirus. The compounds tested exhibited low cytotoxicity and were inactive against a bank of cancer cells in vitro.

  DOI：

  10.1081/ncn-120027814

文献信息

• Synthesis and Antiviral Activity of Novel Fluorinated 2′,3′‐Dideoxynucleosides
  作者：Piyush Kumar、Kazue Ohkura、Jan Balzarini、Erik De Clercq、Koh‐ichi Seki、Leonard I. Wiebe

  DOI：10.1081/ncn-120027814

  日期：2004.1.1

  A series of 5-(trifluoroethoxymethyl)-2',3'-dideoxyuridines and 5-[bis(trifluorroethoxy)-methyl]-2', 3'-dideoxyuri dines have been prepared and screened for antiviral activity. The conformations of these compounds are discussed on the bases of NOE studies and the MO calculations. Modelling and NOE studies suggest both syn- and anti conformations for these 5-(2,2,2-trifluoroethoxymethyl)- and 5-[bis(2,2,2-trifluoroethoxy)-methyl]- derivatives. The NOE parameters are also suggested to be more attributable to the nature of the fluorine atom than to structural or conformational changes. Compounds 17, 26 and 30 showed some activity in anti-HIV-1 and anti-HIV-2 assays, but the compounds were devoid of activity against HSV and human rhinovirus. The compounds tested exhibited low cytotoxicity and were inactive against a bank of cancer cells in vitro.