5-chloro-2'-deoxy-4'-thiouridine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 5-chloro-2'-deoxy-4'-thiouridine
• 英文别名: 5-chloro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl]pyrimidine-2,4-dione；5-chloro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]pyrimidine-2,4-dione
• 化学式: C₉H₁₁ClN₂O₄S
• 分子量: 278.716
• InChiKey: GYSHEQSCWHBMQF-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 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：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (2R,3S)-5-(4-amino-5-chloro-2-oxo-2H-pyrimidin-1-yl)-2-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-thiophen-3-yl ester 在 四丁基氢氧化铵 作用下， 以 甲醇 、 水 为溶剂， 生成 5-chloro-2'-deoxy-4'-thiouridine
  参考文献：
  名称：

  Synthesis and Anti-Herpes Virus Activity of 2‘-Deoxy-4‘-thiopyrimidine Nucleosides

  摘要：

  A series of 5-substituted 2'-deoxy-4'-thiopyrimidine nucleosides was synthesized and evaluated as potential antiviral agents. A number of analogues such as 2'-deoxy-5-propyl-4'-thiouridine (3ii), 2'-deoxy-5-isopropyl-4'-thiouridine (3iii), 5-cyclopropyl-2'-deoxy-4'-thiouridine (3iv), 2'-deoxy-4'-thio-5-vinyluridine (3viii), and 5-(2-chloroethyl)-2'-deoxy-4'-thiouridin (3xx) were found to be highly active against herpes simplex virus type-1 (HSV-1) and varicella tester virus (VZV) in vitro with no significant cytotoxicity. The compound with the broadest spectrum of activity was 2'-deoxy-5-ethyl-4'-thiouridine (3i) which showed significant activity against HSV-1, HSV-2, and VZV.

  DOI：

  10.1021/jm950029r

文献信息

• Antiviral pyrimidine nucleosides
  申请人：THE UNIVERSITY OF BIRMINGHAM

  公开号：EP0409575A1

  公开（公告）日：1991-01-23

  Pyrimidine 4′-thionucleosides of the formula I wherein Y is hydroxy or amino, and X is chloro, bromo, iodo, trifluoromethyl, C₂₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl or C₂₋₆ alkynyl and physiologically functional derivatives thereof. These compounds have utility as anti-viral agents.

  式 I 的嘧啶 4′-硫代核苷 其中 Y 是羟基或氨基，X 是氯、溴、碘、三氟甲基、C₂₋₆ 烷基、C₂₋₆ 烯基、C₂₋₆ 卤代烯基或 C₂₋₆ 烷基及其生理功能衍生物。这些化合物可用作抗病毒剂。
• US5356882A
  申请人：——

  公开号：US5356882A

  公开（公告）日：1994-10-18
• US5521163A
  申请人：——

  公开号：US5521163A

  公开（公告）日：1996-05-28
• [EN] ANTIVIRAL PYRIMIDINE NUCLEOSIDES
  申请人：UNIVERSITY OF BIRMINGHAM

  公开号：WO1991001326A1

  公开（公告）日：1991-02-07

  (EN) Pyrimidine 4'-thionucleosides of formula (I), wherein Y is hydroxy or amino, and X is chloro, bromo, iodo, trifluoromethyl, C2-6 alkyl, C2-6 alkenyl, C2-6 haloalkenyl or C2-6 alkynyl and physiologically functional derivatives thereof. These compounds have utility as anti-viral agents.(FR) L'invention concerne des 4'-thionucléosides à base de pyrimidine de la formule (I), dans laquelle Y représente hydroxy ou amino, et X représente chloro, bromo, iodo, trifluométhyle, alkyle contenant 2 à 6 atomes de carbone, alcényle contenant 2 à 6 atomes de carbone, haloalcényle contenant 2 à 6 atomes de carbone ou alkynyle contenant 2 à 6 atomes de carbone ainsi que leurs dérivés physiologiquement fonctionnels. Ces composés présentent une utilité en tant qu'agents antiviraux.
• [EN] ANOMERISATION PROCESS<br/>[FR] PROCEDE D'ANOMERISATION
  申请人：UNIVERSITY OF BIRMINGHAM

  公开号：WO1994005686A1

  公开（公告）日：1994-03-17

  (EN) A process for producing the $g(a)- or $g(b)-anomer of a nucleoside, which process comprises anomerisation of the $g(b)- or $g(a)-anomer of a nucleoside using an anhydride and a strong acid.(FR) Procédé de production de l'anomère $g(a) ou $g(b) d'un nucléoside, et consistant à anomériser l'anomère $g(a) ou $g(b) d'un nucléoside à l'aide d'un anhydride et d'un acide fort.