1-呋喃戊糖基-2,4(1H,3H)-嘧啶二硫酮 | 13239-96-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 1-呋喃戊糖基-2,4(1H,3H)-嘧啶二硫酮
• 中文别名: 2,4-二硫尿苷
• 英文名称: 2,4-Dithiouridin
• 英文别名: 2,4-Dithiouridine；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dithione
• CAS: 13239-96-8
• 化学式: C₉H₁₂N₂O₄S₂
• 分子量: 276.337
• InChiKey: OKYRYFXQZRFDQL-XVFCMESISA-N

物化性质

• 熔点：
  >146°C (dec.)
• 沸点：
  511.7±60.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、甲醇（微溶、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 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：
  149
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  磷酸三甲酯 、 1-呋喃戊糖基-2,4(1H,3H)-嘧啶二硫酮 在 Proton Sponge 、 三氯氧磷 、 三正丁胺 、 三丁基焦磷酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 2-thio-4-methylthio-uridine-5'-triphosphate
  参考文献：
  名称：

  Synthesis and potency of novel uracil nucleotides and derivatives as P2Y2 and P2Y6 receptor agonists

  摘要：

  The phosphate, uracil, and ribose moieties of uracil nucleotides were varied structurally for evaluation of agonist activity at the human P2Y(2), P2Y(4), and P2Y(6) receptors. The 2-thio modi. cation, found previously to enhance P2Y2 receptor potency, could be combined with other favorable modi. cations to produce novel molecules that exhibit high potencies and receptor selectivities. Phosphonomethylene bridges introduced for stability in analogues of UDP, UTP, and uracil dinucleotides markedly reduced potency. Truncation of dinucleotide agonists of the P2Y(2) receptor, in the form of Up(4)-sugars, indicated that a terminal uracil ring is not essential for moderate potency at this receptor and that specific SAR patterns are observed at this distal end of the molecule. Key compounds reported in this study include 9, alpha, beta-methylene-UDP, a P2Y(6) receptor agonist; 30, Up(4)-phenyl ester and 34, Up(4)-[1] glucose, selective P2Y(2) receptor agonists; dihalomethylene phosphonate analogues 16 and 41, selective P2Y(2) receptor agonists; 43, the 2-thio analogue of INS37217 (P-1-(uridine-5')-P-4-(2'-deoxycytidine-5') tetraphosphate), a potent and selective P2Y(2) receptor agonist. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.05.013
• 作为产物：
  描述：

  2',3',5'-tri-O-acetyl-2,4-dithiouridine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以91%的产率得到1-呋喃戊糖基-2,4(1H,3H)-嘧啶二硫酮
  参考文献：
  名称：

  Synthesis and potency of novel uracil nucleotides and derivatives as P2Y2 and P2Y6 receptor agonists

  摘要：

  The phosphate, uracil, and ribose moieties of uracil nucleotides were varied structurally for evaluation of agonist activity at the human P2Y(2), P2Y(4), and P2Y(6) receptors. The 2-thio modi. cation, found previously to enhance P2Y2 receptor potency, could be combined with other favorable modi. cations to produce novel molecules that exhibit high potencies and receptor selectivities. Phosphonomethylene bridges introduced for stability in analogues of UDP, UTP, and uracil dinucleotides markedly reduced potency. Truncation of dinucleotide agonists of the P2Y(2) receptor, in the form of Up(4)-sugars, indicated that a terminal uracil ring is not essential for moderate potency at this receptor and that specific SAR patterns are observed at this distal end of the molecule. Key compounds reported in this study include 9, alpha, beta-methylene-UDP, a P2Y(6) receptor agonist; 30, Up(4)-phenyl ester and 34, Up(4)-[1] glucose, selective P2Y(2) receptor agonists; dihalomethylene phosphonate analogues 16 and 41, selective P2Y(2) receptor agonists; 43, the 2-thio analogue of INS37217 (P-1-(uridine-5')-P-4-(2'-deoxycytidine-5') tetraphosphate), a potent and selective P2Y(2) receptor agonist. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.05.013

文献信息

• Antisense molecules and method of controlling expression of gene function by using the same
  申请人：——

  公开号：US20030162739A1

  公开（公告）日：2003-08-28

  An antisense molecule which acts on both directions of the inhibition and expression of a gene function and is capable of on-off switching of a gene function appropriately depending on the external factors (orientation controlling factors); and a method for reversibly controlling the expression of a gene function by using the antisense molecule. Such an antisense molecule, which has at least one sugar-base moiety consisting of sugar and a purine or pyrimidine base bonded thereto via a glucoside bond, can bind to a mRNA/gene and/or dissociate therefrom under the orientation control of the base moiety in the molecule by the orientation controlling factors.

  一种反义分子，可以作用于基因功能的抑制和表达的两个方向，并且能够根据外部因素（定向控制因子）适当地开关基因功能；以及一种通过使用该反义分子可逆地控制基因功能表达的方法。这样的反义分子至少包含一个由糖和通过葡苷键连接到糖上的嘌呤或嘧啶碱基部分，可以通过分子中碱基部分的定向控制因子的定向控制，结合到mRNA/基因上，和/或从中解离。
• Oligonucleotides useful for detecting and analyzing nucleic acids of interest
  申请人：——

  公开号：US20040219565A1

  公开（公告）日：2004-11-04

  The invention features improved nucleic acids and methods for expression profiling of mRNAs, identifying and profiling of particular mRNA splice variants, and detecting mutations, deletions, or duplications of particular exons or other splice variants, e.g., alterations associated with a disease such as cancer, in a nucleic acid sample, e.g., a biological sample or a patient sample.

  该发明涉及改进的核酸和表达谱分析mRNA的方法，识别和分析特定mRNA剪接变体，并检测特定外显子或其他剪接变体的突变、缺失或重复，例如与疾病如癌症相关的改变，该样本为核酸样本，例如生物样本或患者样本。
• Population of nucleic acids including a subpopulation of lna oligomers
  申请人：Ramsing Birger Neils

  公开号：US20060147924A1

  公开（公告）日：2006-07-06

  The present invention relates to a population of nucleic acids, said population comprising a first population of nucleic acids of the same length, said length being in the range of 5-15 nucleotides or units, said first population representing at least 1% of the possible different nucleic acid sequences for nucleic acids of said length, at least one nucleic acid in the first population being an LNA (Locked Nucleoside Analogues) oligomer. The population of oligonucleotides is preferably bonded to a solid support. The pluralities of nucleic acids are particularly useful in methods relating to the capture of target nucleic acids, or as probes, e.g. PCR probes. The invention also features LNA oligomers wherein the LNA units have SBC (Selective Binding Complementary) nucleobases.

  本发明涉及一种核酸群体，该群体包括一种长度相同的第一种核酸群体，该长度在5-15个核苷酸或单位的范围内，该第一种群体代表该长度的不同核酸序列中至少1％，第一种群体中至少有一个核酸是LNA（锁定核苷酸类似物）寡聚体。寡核苷酸的群体最好与固定支撑物结合。这些核酸的多样性在与目标核酸的捕获相关的方法或作为探针，例如PCR探针的方法中特别有用。本发明还涉及具有SBC（选择性结合互补）核碱基的LNA寡聚体。
• OLIGONUCLEOTIDES USEFUL FOR DETECTING AND ANALYZING NUCLEIC ACIDS OF INTEREST
  申请人：Kauppinen Sakari

  公开号：US20120157333A1

  公开（公告）日：2012-06-21

  The invention features improved nucleic acids and methods for expression profiling of mRNAs, identifying and profiling of particular mRNA splice variants, and detecting mutations, deletions, or duplications of particular exons or other splice variants, e.g., alterations associated with a disease such as cancer, in a nucleic acid sample, e.g., a biological sample or a patient sample.

  这项发明涉及改进的核酸和表达谱分析mRNA的方法，识别和分析特定的mRNA剪接变体，以及检测特定外显子或其他剪接变体的突变、缺失或复制，例如与疾病如癌症相关的变化，可以在核酸样品中进行检测，例如生物样品或患者样品。
• ANTISENSE MOLECULES AND METHOD OF CONTROLLING EXPRESSION OF GENE FUNCTION BY USING THE SAME
  申请人：JAPAN SCIENCE AND TECHNOLOGY CORPORATION

  公开号：EP1295892A1

  公开（公告）日：2003-03-26

  An antisense molecule which acts on both directions of the inhibition and expression of a gene function and is capable of on-off switching of a gene function appropriately depending on the external factors (orientation controlling factors); and a method for reversibly controlling the expression of a gene function by using the antisense molecule. Such an antisense molecule, which has at least one sugar-base moiety consisting of sugar and a purine or pyrimidine base bonded thereto via a glucoside bond, can bind to a mRNA/gene and/or dissociate therefrom under the orientation control of the base moiety in the molecule by the orientation controlling factors.

  一种反义分子，它对基因功能的抑制和表达具有双向作用，并能根据外部因素（定向控制因素）适当地开关基因功能；以及一种利用该反义分子可逆地控制基因功能表达的方法。这种反义分子至少有一个糖基分子，由糖和嘌呤或嘧啶碱基通过葡糖苷键结合而成，在取向控制因子对分子中碱基分子的取向控制下，可与mRNA/基因结合和/或从mRNA/基因中分离出来。