5-trifluoromethyl-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-trifluoromethyl-3'-fluoro-2',3'-dideoxyuridine
• 英文别名: 3'-fluoro-2',3'-dideoxy-5-trifluoromethyluridine；1-(2,3-dideoxy-3-fluoro-β-D-erythro-pentofuranosyl)5-trifluoromethyluracil；1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione；1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione
• 化学式: C₁₀H₁₀F₄N₂O₄
• 分子量: 298.194
• InChiKey: KZNAVPLPVSOYFG-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  三氟胸苷 在 4-二甲氨基吡啶 、 二乙胺基三氟化硫 、 水 、 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 水 、 苯 为溶剂， 反应 2.5h， 生成 5-trifluoromethyl-3'-fluoro-2',3'-dideoxyuridine
  参考文献：
  名称：

  Antimycobacterial activities of 5-alkyl (or halo)-3′-substituted pyrimidine nucleoside analogs

  摘要：

  Several 5-alkyl (or halo)-3'-azido (amino or halo) analogs of pyrimidine nucleosides have been synthesized and evaluated against Mycobacterium bovis, Mycobacterium tuberculosis and Mycobacterium avium. Among these compounds, 3'-azido-5-ethyl-2',3'-dideoxyuridine (3) was found to have significant antimycobacterial activities against M. bovis (MIC50 = 1 mu g/mL), M. tuberculosis (MIC50 = 10 mu g/mL) and M. avium (MIC50 = 10 mu g/mL). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.114

文献信息

• Antiviral agents
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0457326A1

  公开（公告）日：1991-11-21

  Nucleoside compounds of the formula wherein:    B is a purine or a pyrimidine;    X and X' are H, OH or F, provided that at least one is H;    Y and Y' are H, OH, OCH₃ or F, provided that at least one is H;    Y' and Z together form a cyclic phosphate ester, provided that Y is H; or Z is where n is zero, one, two or three; and Z' is N₃ or OCH₃;    provided that whenX' and Y' are OH and Z' is N₃, B is not cytosine, whenX' and Y' are OH and Z' is OCH₃, B is not uracil, adenine or cytosine, and whenZ' is N₃, X' is H, and Y' is H, OH, OCH₃, or F, B is not purine, cytosine, uracil, or thymine; and the pharmaceutically acceptable esters, ethers and salts thereof, have been found to have potent antiviral activity with a high therapeutic ratio.

  式中的核苷化合物 其中 B 是嘌呤或嘧啶； X 和 X'是 H、OH 或 F，但至少有一个是 H； Y 和 Y'是 H、OH、OCH₃ 或 F，但至少有一个是 H； Y' 和 Z 共同形成环磷酸酯，条件是 Y 是 H；或 Z 是 其中 n 为 0、1、2 或 3；以及 Z' 是 N₃ 或 OCH₃； 条件是 当 X' 和 Y' 为 OH 且 Z' 为 N₃ 时，B 不是胞嘧啶、 当X'和Y'为OH且Z'为OCH₃时，B不是尿嘧啶、腺嘌呤或胞嘧啶，以及 当 Z' 是 N₃，X' 是 H，Y' 是 H、OH、OCH₃ 或 F 时，B 不是嘌呤、胞嘧啶、尿嘧啶或胸腺嘧啶； 及其药学上可接受的酯、醚和盐，已被发现具有强效抗病毒活性和高治疗比。
• US5449664A
  申请人：——

  公开号：US5449664A

  公开（公告）日：1995-09-12
• Antimycobacterial activities of 5-alkyl (or halo)-3′-substituted pyrimidine nucleoside analogs
  作者：Naveen C. Srivastav、Neeraj Shakya、Sudha Bhavanam、Amogh Agrawal、Chris Tse、Nancy Desroches、Dennis Y. Kunimoto、Rakesh Kumar

  DOI：10.1016/j.bmcl.2011.11.114

  日期：2012.1

  Several 5-alkyl (or halo)-3'-azido (amino or halo) analogs of pyrimidine nucleosides have been synthesized and evaluated against Mycobacterium bovis, Mycobacterium tuberculosis and Mycobacterium avium. Among these compounds, 3'-azido-5-ethyl-2',3'-dideoxyuridine (3) was found to have significant antimycobacterial activities against M. bovis (MIC50 = 1 mu g/mL), M. tuberculosis (MIC50 = 10 mu g/mL) and M. avium (MIC50 = 10 mu g/mL). (C) 2011 Elsevier Ltd. All rights reserved.