5-fluoro-4-thiouridine | 727-79-7

• 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-fluoro-4-thiouridine
• 英文别名: 5-Fluoro-1-beta-D-ribofuranosyl-4-sulfanylidene-3,4-dihydropyrimidin-2(1H)-one；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-4-sulfanylidenepyrimidin-2-one
• CAS: 727-79-7
• 化学式: C₉H₁₁FN₂O₅S
• 分子量: 278.261
• InChiKey: WYQCVEGKYDIJJY-UAKXSSHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  18
• 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：
  134
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-fluoro-4-thiouridine 、 beta-胸苷 以 水 为溶剂， 生成 7-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-(4-hydroxy-5-hydroxy-methyl-tetrahydro-furan-2-yl)-4a-methyl-4a,9a-dihydro-1H,7H-9-thia-1,3,5,7-tetraaza-fluorene-2,4,6-trione 、 7-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-(4-hydroxy-5-hydroxy-methyl-tetrahydro-furan-2-yl)-4a-methyl-4a,9a-dihydro-1H,7H-9-thia-1,3,5,7-tetraaza-fluorene-2,4,6-trione
  参考文献：
  名称：

  Photoinduced Fluorescent Cross-Linking of 5-Chloro- and 5-Fluoro-4-thiouridines with Thymidine

  摘要：

  Two highly fluorescent, thermally stable diastereomeric photoadducts, 3a,b, are formed when either 5-chloro-4-thiouridine, 1, or 5-fluoro-4-thiouridine, 2, are photoexcited with 366 nm UV light in the presence of thymidine (T). 5-Fluoro-4-thiouridine, 2, exhibits photoreactivity much higher than that of the 5-chloro derivative 1. In both cases the photoreaction is very clean, leading to highly eficient conversion of the 5-halogeno-4-thiouridine (1, 2) and T to photoadducts 3a,b. The identity and structure of 3a was confirmed using mass spectrometry and 2-D NMR. The epimeric relationship of 3a,b was established by UV circular dichroism spectroscopy. The geometry of the fluorescent photoadduct is consistent with formation of an interstrand cross-link in a DNA duplex if 1 or 2 is flanked by T in an opposite strand.

  DOI：

  10.1021/jo902136k
• 作为产物：
  描述：

  5-氟尿嘧啶核苷 在 吡啶 、 tetraphosphorus decasulfide 、 氨 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 11.0h， 生成 5-fluoro-4-thiouridine
  参考文献：
  名称：

  5-取代-4-硫代嘧啶核苷核磁共振谱的系统归属

  摘要：

  使用 NMR 光谱对 5-取代-4-硫代嘧啶核苷（核糖核苷和 2'-脱氧核苷）进行明确表征。5-溴-4-硫尿苷和相关核苷的所有质子和碳信号的分配是通过 COZY 和 HMQC 技术系统地进行并牢固建立的。比较了各种 4-硫代嘧啶核苷的 NMR 数据，并讨论了关键影响因素。这里介绍的方法适用于其他修饰的核苷和核苷酸，以及核碱基。版权所有 © 2013 John Wiley & Sons, Ltd.

  DOI：

  10.1002/mrc.3980

文献信息

• Anti-HCV nucleoside derivatives
  申请人：——

  公开号：US20030008841A1

  公开（公告）日：2003-01-09

  The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

  本发明涉及新颖和已知的嘌呤和嘧啶核苷衍生物，已发现这些衍生物对丙型肝炎病毒（HCV）具有活性。本发明声明利用这些衍生物治疗HCV感染，以及本文所披露的新颖核苷衍生物。
• NUCLEOSIDE DERIVATIVES FOR THE TREATMENT OF HEPATITIS C
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1315736A2

  公开（公告）日：2003-06-04
• Photocrosslinking probes and uses of the same
  申请人：Franzen Stefan

  公开号：US20070082349A1

  公开（公告）日：2007-04-12

  A method of detecting a target nucleic acid is disclosed, the method comprising detecting the presence of a fluorescent covalent crosslinked product from non-fluorescent precursors. The fluorescent covalent crosslinked product comprises a novel fluorophore structure. Also described are methods of synthesizing probe molecules that can form fluorescent covalent crosslinked products with nucleic acid targets and arrays comprising such probes.
• TRIGGERED COVALENT PROBES FOR IMAGING AND SILENCING GENETIC EXPRESSION
  申请人：Pierce Niles A.

  公开号：US20110288148A1

  公开（公告）日：2011-11-24

  The present invention relates to the use of cross-linking probes to covalently bind probes to nucleic acid targets. In some embodiments, the probe comprises an initiator region that is able to bind to a first portion of a target nucleic acid, a probe region linked too the initiator region that is able to bind to a second region of the target nucleic acid and that comprises one or more cross-linkers, and a blocking region hybridized to the probe region.
• US7868161B2
  申请人：——

  公开号：US7868161B2

  公开（公告）日：2011-01-11