1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl]-5-nitro-pyrimidine-2,4-dione

• 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: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl]-5-nitro-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]-5-nitropyrimidine-2,4-dione
• 化学式: C₉H₁₁N₃O₆S
• 分子量: 289.269
• InChiKey: IAGKOEAPVAYACR-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  19
• 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：
  161
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-O-acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-ribofuranose 在 ammonium sulfate 、 三乙基氯硅烷 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 生成 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl]-5-nitro-pyrimidine-2,4-dione
  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

• Further antiviral pyrimidine nucleosides
  申请人：THE UNIVERSITY OF BIRMINGHAM

  公开号：EP0421777A1

  公开（公告）日：1991-04-10

  Pyrimidine 4′-thionucleosides of the formula (I) where B¹ is a pyrimidine base; and either (a) R² is hydrogen and R³ is hydroxy or fluoro, or (b) R² is hydroxy and R³ is hydrogen, hydroxy or fluoro, or (c) R² is fluoro and R³ is hydrogen or hydroxy, or (d) R² and R³ together form a carbon-carbon bond; and physiologically functional derivatives thereof and processes for their production. Preferably, the base B¹ is of the formula (II) wherein Y is hydroxy or amino, monoalkylamino or dialkylamino; and X is halogen, alkoxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, amino, monoalkylamino, dialkylamino, cyano or nitro. The compounds are useful in the treatment of viral infections.

  式(I)的嘧啶-4′-硫代核苷 其中 B¹ 是嘧啶碱； (a) R² 是氢，R³ 是羟基或氟、 或 (b) R² 是羟基，R³ 是氢、羟基或氟、 或 (c) R² 是氟，R³ 是氢或羟基、 或 (d) R² 和 R³ 共同形成碳-碳键；以及其生理功能衍生物及其生产工艺。碱 B¹ 最好为式 (II) 其中 Y 是羟基或氨基、单烷基氨基或二烷基氨基；X 是卤素、烷氧基、烷基、卤代烷基、烯基、卤代烯基、炔基、氨基、单烷基氨基、二烷基氨基、氰基或硝基。这些化合物可用于治疗病毒感染。
• ANTIVIRAL PYRIMIDINE NUCLEOSIDES
  申请人：THE UNIVERSITY OF BIRMINGHAM

  公开号：EP0658166A1

  公开（公告）日：1995-06-21
• JPH08504753A
  申请人：——

  公开号：JPH08504753A

  公开（公告）日：1996-05-21
• [EN] ANTIVIRAL PYRIMIDINE NUCLEOSIDES<br/>[FR] NUCLEOSIDES PYRIMIDINIQUES ANTIVIRAUX
  申请人：UNIVERSITY OF BIRMINGHAM

  公开号：WO1994005687A1

  公开（公告）日：1994-03-17

  (EN) Antiviral nucleosides of formula (I), wherein: Y is hydroxy or amino; X is hydrogen, hydroxy, mercapto, halo, trifluoromethyl, methyl, C2-6alkyl, C1-6haloalkyl, hydroxyC1-3alkyl, formyl, C2-6alkenyl, C2-6haloalkenyl, C2-6alkynyl, C1-6alkoxy, C1-6alkylthio, C1-6alkoxyC1-2alkyl, C1-6alkylthiomethyl, amino, monoC1-6alkylamino, diC1-6alkylamino, cyano, thiocyanate or nitro; R2 is hydrogen and R3 is hydroxy or hydrogen, or together R2 and R3 form a carbon-carbon bond; and physiologically functional derivatives thereof. Compositions containing the compounds, their use in treatment and therapy of viral disease, and processes for the production of the compounds are also provided.(FR) L'invention concerne des nucléosides antiviraux de la formule (I). Dans cette formule: Y représente un hydroxy ou un amino; X représente un hydrogène, un hydroxy, un mercapto, un halo, un trifluorométhyle, un méthyle, un alkyleC2-6, un haloalkyleC1-6, un hydroxyalkyleC1-3, un formyle, un alcényleC2-6, un haloalcényleC2-6, un alcynyleC2-6, un alcoxyC1-6, un alkylthioC1-6, un alcoxyC1-6alkyleC1-2, un alkylthiométhyleC1-6, un amino, un monoC1-6alkylamino, un diC1-6alkylamino, un cyano, un thiocyanate ou un nitro; R2 représente un hydrogène et R3 représente un hydroxy ou un hydrogène ou R2 et R3 forment ensemble une liaison carbone-carbone. On décrit également des dérivés de ces composés actifs sur le plan physiologique, des compositions contenant ces composés, leur utilisation pour traiter et soigner des maladies virales et des procédés pour produire ces composés.
• [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.