2',3'-O-(1-甲基亚乙基)-5-(1-吡咯烷基甲基)-2-硫代尿苷 | 89845-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2',3'-O-(1-甲基亚乙基)-5-(1-吡咯烷基甲基)-2-硫代尿苷
• 英文名称: 2',3'-O-isopropylidene-5-pyrrolidinomethyl-2-thiouridine
• 英文别名: 1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-5-(pyrrolidin-1-ylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one；1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-(pyrrolidin-1-ylmethyl)-2-sulfanylidenepyrimidin-4-one
• CAS: 89845-82-9
• 化学式: C₁₇H₂₅N₃O₅S
• 分子量: 383.469
• InChiKey: IFJTVPASSJKUFD-RGCMKSIDSA-N

物化性质

• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2',3'-O-(1-甲基亚乙基)-5-(1-吡咯烷基甲基)-2-硫代尿苷 以 丙酮 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  5-羧甲基氨基甲基尿苷和5-羧甲基氨基甲基-2-硫尿苷的合成

  摘要：

  2'，3'- Ô -Isopropylideneuridine（1A）和2'，3'- ö异亚丙基-2-硫代尿苷（1B）被转换以4个步骤，通过相应的曼尼期碱（2A）和（2B），进修饰的核苷（5a）和（5b）。

  DOI：

  10.1039/c39840000062
• 作为产物：
  描述：

  四氢吡咯 、 聚合甲醛 、 2',3'-O-异丙亚基-2-硫代尿苷 以 水 为溶剂， 反应 1.0h， 以70%的产率得到2',3'-O-(1-甲基亚乙基)-5-(1-吡咯烷基甲基)-2-硫代尿苷
  参考文献：
  名称：

  5-羧甲基氨基甲基尿苷和5-羧甲基氨基甲基-2-硫尿苷的合成

  摘要：

  2'，3'- Ô -Isopropylideneuridine（1A）和2'，3'- ö异亚丙基-2-硫代尿苷（1B）被转换以4个步骤，通过相应的曼尼期碱（2A）和（2B），进修饰的核苷（5a）和（5b）。

  DOI：

  10.1039/c39840000062

文献信息

• Compositions and methods for the identification of inhibitors of retroviral infection
  申请人：Trana Discovery, Inc.

  公开号：US09249473B2

  公开（公告）日：2016-02-02

  Methods of identifying inhibitors of retroviral propagation, tRNA used in the methods, and kits, including the tRNA, which can be used in the methods, are disclosed. Methods of treating or preventing retroviral infections by administering an effective amount of the inhibitors, and pharmaceutical compositions including the inhibitors, are also disclosed. The methods involve forming a mixture comprising a linear sequence of a tRNA anticodon stem loop fragment that is not capable of forming a stem-loop, a target nucleic acid molecule capable of binding to the tRNA anticodon stem loop fragment, and a test compound. The mixture is incubated under conditions that allow binding of the tRNA anticodon stem loop fragment and the target nucleic acid molecule in the absence of the test compound. Assays can then be performed that detect whether or not the test compound inhibits the binding of the tRNA anticodon stem loop fragment and the target nucleic acid molecule.

  公开了用于识别逆转录病毒传播抑制剂的方法、用于这些方法的tRNA，以及包括可以在这些方法中使用的tRNA的试剂盒。还公开了通过给予有效量的抑制剂来治疗或预防逆转录病毒感染的方法，以及包括这些抑制剂的药物组合物。这些方法涉及形成一个混合物，其中包括一个不具备形成茎环的tRNA反密码子茎环片段的线性序列，一个能够结合到tRNA反密码子茎环片段的靶核酸分子，以及一个测试化合物。在没有测试化合物的情况下，将混合物在允许tRNA反密码子茎环片段和靶核酸分子结合的条件下孵育。然后可以进行检测，以确定测试化合物是否抑制了tRNA反密码子茎环片段和靶核酸分子的结合。
• Chemical Synthesis and Properties of 5-Taurinomethyluridine and 5-Taurinomethyl-2-thiouridine
  作者：Toshihiko Ogata、Tomomi Shimazaki、Tadashi Umemoto、Shinya Kurata、Takashi Ohtsuki、Tsutomu Suzuki、Takeshi Wada

  DOI：10.1021/jo802697r

  日期：2009.3.20

  Unique taurine-containing Uridine derivatives, 5-taurinomethyluridine (tau m(5)U) and 5-taurinomethyl-2-thiouridine (tau m(5)s(2)U), which were discovered in mammalian mitochondrial tRNAs, exist at the first position of the anticodon. In this paper, we report the first efficient synthesis of tau m(5)U and tau m(5)s(2)U and describe their physicochemical properties. These modified ribonucleosides were synthesized by the reaction of 5-substituted uridine derivatives with a tetrabutylammonium salt of taurine that is highly reactive and well-soluble in common organic solvents. UV and H-1 NMR spectrometric studies revealed the structural properties of the taurine-containing base moieties and the Sugar conformations of these modified ribonucleosides.
• COMPOSITIONS AND METHODS FOR THE IDENTIFICATION OF INHIBITORS OF PROTEIN SYNTHESIS
  申请人：GUENTHER Richard H.

  公开号：US20080199870A1

  公开（公告）日：2008-08-21

  Compositions and methods for identifying inhibitors of RNA-target molecule interactions are provided as well as identifying inhibitors that block the role of tRNA in protein synthesis. The methods involve forming a mixture comprising a tRNA fragment molecule containing a modified nucleotide, a target molecule capable of binding to the tRNA fragment, and a test compound. The mixture is incubated under conditions that allow binding of the tRNA and the target molecule in the absence of the test compound. Assays can then be performed that detect whether or not the test compound inhibits the binding of the tRNA molecule and the target molecule. High throughput assays are also provided.
• US7598040B2
  申请人：——

  公开号：US7598040B2

  公开（公告）日：2009-10-06
• US8232378B2
  申请人：——

  公开号：US8232378B2

  公开（公告）日：2012-07-31