4'-硫代-5-乙基-2'-脱氧尿苷 | 134699-96-0

• 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
• 中文名称: 4'-硫代-5-乙基-2'-脱氧尿苷
• 英文名称: 4'-thio-5-ethyl-2'-deoxyuridine
• 英文别名: 2'-deoxy-5-ethyl-4'-thiouridine；5-ethyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]pyrimidine-2,4-dione
• CAS: 134699-96-0
• 化学式: C₁₁H₁₆N₂O₄S
• 分子量: 272.325
• InChiKey: ONBZWIKPRXQNFE-DJLDLDEBSA-N

物化性质

• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4'-硫代-5-乙基-2'-脱氧尿苷 在 溶剂黄146 作用下， 以 吡啶 为溶剂， 反应 44.0h， 生成 3'-O-acetyl-5-ethyl-4'-thio-2'-deoxyuridine
  参考文献：
  名称：

  Some Reactions of 4′-Thionucleosides and Their Sulfones

  摘要：

  We report interesting and novel reactions of 4'-thionucleosides and their sulfone derivatives when a good leaving group is present in the 5'-position. The results have important implications for the phosphorylation of these nucleoside analogues by standard chemical procedures. Possible mechanisms for these reactions are discussed.

  DOI：

  10.1080/07328319608002376
• 作为产物：
  描述：

  5-乙基-2,4-二[(三甲基硅烷基)氧基]嘧啶 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.0h， 生成 4'-硫代-5-乙基-2'-脱氧尿苷
  参考文献：
  名称：

  4'-Thio-Nucleosides via in Situ Pyranose-Furanose Rearrangements: A Short Synthesis of the Antiherpes Agent 2'-Deoxy-5-ethyl-4'-thiouridine via Direct Coupling of a Silylated Pyrimidine Base with a 4-Thiopyranose Sugar

  摘要：

  Methyl 2-deoxy-3,4-0-thiocarbonyl-beta-D-ribopyranoside was converted into the thione carbonate by reaction with thiophosgene. Bromide ion-catalyzed 0-S rearrangement produced methyl 2-deoxy-3-0,4-S-carbonyl-4-thio-beta-D-ribopyranoside (3a) and the 3-0,4-S isomer 3b. The carbonates were cleaved with ammonia and the 3-0,4-S pyranoside sugar coupled with bis(trimethylsilyl)-5-ethyluracil using trimethylsilyl triflate to provide the antiherpes agent 2'-deoxy-5-ethyl-4'-thiouridine 9. The reaction proceeded via in, situ pyranoside rearrangement-of the sugar and subsequent coupling. The pyranoside sugar could also be converted to the furanoside form with Dowex H+ acid resin and coupled in conventional fashion to give the nucleoside. Coupling of methyl 4-0-carbamoyl-2-deoxy-3-thio-beta-D-ribopyranoside (4b) with the bis(trimethylsilyl)-5-ethyluracil gave 1-[2-[2-(hydroxymethyl)thiiran-1-yl]-1-methoxyethyl]-5-ethyluracil.

  DOI：

  10.1021/jo00121a039

文献信息

• Acyl carbamate directing groups in nucleoside synthesis: Applications in the synthesis of 2′-deoxy-5-ethyl-4′-thiouridine
  作者：Sue Shaw-Ponter、Gail Mills、Mark Robertson、Roy D. Bostwick、George W. Hardy、Robert J. Young

  DOI：10.1016/0040-4039(96)00138-4

  日期：1996.3

  The use of the 3-O-(N-acyl)carbamoyl directing groups in the synthesis of the potent anti-Herpes virus agent 2′-deoxy-5-ethyl-4′-thio-D-uridine is described. This includes details of experiments to optimise the carbamate substitution and a multi-gram exemplification of the key steps.

  描述了在有效的抗疱疹病毒试剂2'-脱氧-5-乙基-4'-硫代-D-尿苷的合成中使用3- O-（N-酰基）氨基甲酰基指导基团。这包括优化氨基甲酸酯替代的实验细节以及关键步骤的多克例证。
• Antiviral pyrimidine nucleosides and methods for using same
  申请人：University of Birmingham

  公开号：US05521163A1

  公开（公告）日：1996-05-28

  1'-Deoxy-5-ethyl-4'-thio-.beta.-uridine as a compound including its physiologically functional derivatives, pharmaceutical compositions containing it and methods of treating herpes virus infections are described.

  本文描述了1'-去氧-5-乙基-4'-硫基-β-脱氧尿嘧啶及其生理功能衍生物、含有该化合物的制药组合物以及治疗疱疹病毒感染的方法。
• Antiviral pyrimidine nucleosides
  申请人：University of Birmingham

  公开号：US05356882A1

  公开（公告）日：1994-10-18

  Pyrimidine 4'-thionucleosides of the formula I ##STR1## wherein Y is hydroxy or amino, and X is chloro, bromo, iodo, trifluoromethyl, C.sub.2-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 haloalkenyl or C.sub.2-6 alkynyl and physiologically functional derivatives thereof. These compounds have utility as anti-vital agents.

  式I的嘧啶4'-硫核苷，其中Y为羟基或氨基，X为氯、溴、碘、三氟甲基、C.sub.2-6烷基、C.sub.2-6烯基、C.sub.2-6卤代烯基或C.sub.2-6炔基及其生理学上的功能衍生物。这些化合物具有作为抗病毒剂的功用。
• Synthesis and Anti-Herpes Virus Activity of 2‘-Deoxy-4‘-thiopyrimidine Nucleosides
  作者：S. George Rahim、Naimisha Trivedi、Mirjana V. Bogunovic-Batchelor、George W. Hardy、Gail Mills、John W. T. Selway、Wendy Snowden、Edward Littler、Paul L. Coe、Ivan Basnak、Robert F. Whale、Richard T. Walker

  DOI：10.1021/jm950029r

  日期：1996.1.1

  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.
• Otter, Graham P.; Elzagheid, Mohamed I.; Jones, Garry D., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 11, p. 2343 - 2349
  作者：Otter, Graham P.、Elzagheid, Mohamed I.、Jones, Garry D.、MacCulloch, Alasdair C.、Walker, Richard T.、Oivanen, Mikko、Klika, Karel D.

  DOI：——

  日期：——