3',5'-dithiothymidine | 183428-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3',5'-dithiothymidine
• 英文别名: 5-methyl-1-[(2R,4S,5R)-4-sulfanyl-5-(sulfanylmethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 183428-19-5
• 化学式: C₁₀H₁₄N₂O₃S₂
• 分子量: 274.365
• InChiKey: GWBNTUNGWHMFMJ-GJMOJQLCSA-N

物化性质

• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3',5'-dithiothymidine 在 二正丁基氧化锡 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 3′,5′-dideoxy-3′,5′-bis-S-[(methoxycarbonyl)methylthio]thymidine
  参考文献：
  名称：

  3′-Oxo-, amino-, thio- and sulfone-acetic acid modified thymidines: Effect of increased acidity on ribonuclease A inhibition

  摘要：

  A family of 3'-functionalized thymidines carrying XCH2COOH (X = O, NH, S, SO2) groups has been designed as inhibitors of RNase A. This is because it is possible to manipulate the overall acidity of this new class of nucleic 'acids' by changing X from oxygen to the SO2 group in the series. It is also expected that the acyclic nature of the XCH2COOH group would provide enough flexibility to the -COOH group to have maximum interactions with the catalytic subsite P-1 of RNase A. As the -SO2CH2COOH substituted derivative showed better potency partially because of the increased acidity of the -COOH group, the inhibitory properties of both 5'-substituted and 3',5'-disubstituted sulfone acetic acid modified thymidines were investigated. Two -SO2CH2COOH groups were incorporated with the expectation of targeting two phosphate binding sites simultaneously. Thus, 3',5'-dideoxy-3',5'-bis-S-[(carboxymethyl)sulfonyl]thymidine emerged as the best inhibitor in this series with a K-i value of 25 +/- 2 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.047
• 作为产物：
  描述：

  5-O-(4-甲基苯基磺酰基)胸腺嘧啶脱氧核苷 在 吡啶 、 lithium aluminium tetrahydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙腈 为溶剂， 反应 106.0h， 生成 3',5'-dithiothymidine
  参考文献：
  名称：

  二硫骨架核酸的研究：第 2 部分. 3',5'-二硫胸苷的高效合成

  摘要：

  描述了一种新的和方便的合成 3',5'-二硫胸苷的方法。在此过程中，DBU 用于形成 2,3'-脱水胸苷的分子内环，然后使用硫代乙酸作为溶剂和亲核试剂以生产 S-乙酰基-3'-硫代胸苷。应用非常有效的脱保护步骤来提供目标化合物，这可以避免硫醇基团的氧化。并且发现关键中间体 5'-O-tosyl-2,3'-脱水胸苷对不同的亲核试剂具有区域选择性。

  DOI：

  10.1246/cl.2005.432

文献信息

• Synthesis of 3′,5′-dithiothymidine and related compounds
  作者：Alessandra Eleuteri、Colin B. Reese、Quanlai Song

  DOI：10.1039/p19960002237

  日期：——

  acid–dichloromethane (1:9 v/v) at 0 °C and then with zinc in hot acetic acid gives 3′,5′-dithiothymidine 5a and the cyclic disulfide 16, respectively, as crystalline solids in good overall yields. Although attempts to isolate the pure threo-dithio compoun 12b lead to the formation of the cyclic disulfide 16, when the crude material is treated with 2,2-dimethoxypropane in the presence of acid, its 3′,5′-S-isopropylidene

  当先在乙醇溶液中用三乙胺加热3'，5'-二-O-甲硫基胸苷7然后在N，N-二甲基乙酰胺（DMA）溶液中用4-甲氧基苯基甲硫醇9的钠盐加热时，双（硫化物）11a为高产 当dimesyl酯7与在六甲基磷酰三胺（HMPA）溶液相同的硫醇盐在室温下处理时，苏立体定向获得-双（硫化物）12a。首先在0°C下于乙酸-二氯甲烷（1：9 v / v）中用2-硝基苯亚磺酰氯10处理两个双（硫化物）11a和12a，然后在热乙酸中用锌处理，得到3'，5'-二硫代胸腺嘧啶核苷5a和环状二硫化物16分别为结晶固体，总收率良好。尽管尝试分离纯的苏-二硫代化合物12b导致形成环状二硫键16，但在酸存在下用2,2-二甲氧基丙烷处理粗材料时，其3'，5'- S-异亚丙基衍生物得到17，并以良好的总产率分离为结晶固体。
• Artificial Nucleosides Possessing Metal Binding Sites at the 3‘- and 5‘-Positions of the Deoxyribose Moieties
  作者：Jun-ya Chiba、Kentaro Tanaka、Yukinori Ohshiro、Ryosuke Miyake、Shuichi Hiraoka、Motoo Shiro、Mitsuhiko Shionoya

  DOI：10.1021/jo026026l

  日期：2003.1.1

  This paper describes a convenient synthetic procedure for nucleoside mimics, 1-6, in which the 3',5'-hydroxy groups of natural 2'-deoxythymidine or 2'-deoxyadenosine are replaced by thiol, amine, or alkylthiol groups. Such nucleosides would be built up into a single DNA strand with cooperative participation of metal coordination, where internucleoside linkages are replaced by metal complexation motifs. The X-ray crystal structure and complexation behaviors of 3',5'-dithiothymidine, 1, with Au-I are also reported.
• 3′-Oxo-, amino-, thio- and sulfone-acetic acid modified thymidines: Effect of increased acidity on ribonuclease A inhibition
  作者：Dhrubajyoti Datta、Anirban Samanta、Swagata Dasgupta、Tanmaya Pathak

  DOI：10.1016/j.bmc.2013.05.047

  日期：2013.8

  A family of 3'-functionalized thymidines carrying XCH2COOH (X = O, NH, S, SO2) groups has been designed as inhibitors of RNase A. This is because it is possible to manipulate the overall acidity of this new class of nucleic 'acids' by changing X from oxygen to the SO2 group in the series. It is also expected that the acyclic nature of the XCH2COOH group would provide enough flexibility to the -COOH group to have maximum interactions with the catalytic subsite P-1 of RNase A. As the -SO2CH2COOH substituted derivative showed better potency partially because of the increased acidity of the -COOH group, the inhibitory properties of both 5'-substituted and 3',5'-disubstituted sulfone acetic acid modified thymidines were investigated. Two -SO2CH2COOH groups were incorporated with the expectation of targeting two phosphate binding sites simultaneously. Thus, 3',5'-dideoxy-3',5'-bis-S-[(carboxymethyl)sulfonyl]thymidine emerged as the best inhibitor in this series with a K-i value of 25 +/- 2 mu M. (C) 2013 Elsevier Ltd. All rights reserved.
• Study on Disulfur-backboned Nucleic Acid: Part 2. Efficient Synthesis of 3′,5′-Dithiothymidine
  作者：Hua Wang、Changmei Cheng、Hongchao Zheng、Xiaohong Liu、Chang Fang、Shanshan Xu、Yufen Zhao

  DOI：10.1246/cl.2005.432

  日期：2005.3

  novel and convenient procedure for synthesizing 3',5'-dithiothymidine was described. In this procedure, DBU was used to form the intramolecular ring of 2,3'-anhydrothymidine and then the thioacetic acid was used as solvent as well as the nucleophilic reagent to produce S-acetyl-3'-thiothymidine. A very efficient deprotection step was applied to afford the target compound, which can avoid the oxidization

  描述了一种新的和方便的合成 3',5'-二硫胸苷的方法。在此过程中，DBU 用于形成 2,3'-脱水胸苷的分子内环，然后使用硫代乙酸作为溶剂和亲核试剂以生产 S-乙酰基-3'-硫代胸苷。应用非常有效的脱保护步骤来提供目标化合物，这可以避免硫醇基团的氧化。并且发现关键中间体 5'-O-tosyl-2,3'-脱水胸苷对不同的亲核试剂具有区域选择性。