5-iodo-2'-deoxyuridine | 71701-05-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-iodo-2'-deoxyuridine
• 英文别名: 1-(3-deoxy-β-D-erythropentofuranosyl)-5-iodouracil；5-Iodo-3 '-deoxyuridine；3'-deoxy-5-iodouridine；5-Iodo-3'-deoxyuridine；1-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione
• CAS: 71701-05-8
• 化学式: C₉H₁₁IN₂O₅
• 分子量: 354.101
• InChiKey: LBIBNVPSZYOXOG-CVTKMRTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 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：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 5-iodo-2'-deoxyuridine 在 吡啶 、 六甲基二硅氮烷 作用下， 反应 1.0h， 以98%的产率得到5-iodo-2'-deoxy-3',5'-(diOTMS)uridine
  参考文献：
  名称：

  Synthèe, caractérisation et propriétés cytotoxiques des premiers ‘métallocénonucléosides’

  摘要：

  The synthesis of the first 'metallocenonucleosides' (nucleosides containing a metallocenic moiety in their framework) of the formula Ns-C = C-Fc, Ns-CH = CH-Fc and Ns-CH2-CH2-Fc (Ns = uridine, deoxyuridine, adenosine; Fc: C5H4FeC5H5) has been conducted in the presence of palladium salt according to the following routes: i) reaction of a 5-chloromercuri-nucleoside on ethynylferrocene; ii) hydrozirconation (Schwartz' reagent) of ethynylferrocene followed by the reaction of a 5-halogeno nucleoside; iii) direct coupling between ethynylferrocene and a 5-halogeno nucleoside. The same procedures allowed the synthesis of the corresponding 'metallocenonucleobases' Nb-C = C-Fc, Nb-CH = CH-Fc and NbCH2CH2Fc (Nb = uracil, cytosine, adenine) which have also been prepared by acid solvolysis of the nucleosides precursors. The compounds obtained were purified by HPLC technique and were characterized by H-1 NMR and mass spectrometry. The cytotoxicity in vitro has been studied on L 1210 cells. Only modest activity has been observed.

  DOI：

  10.1016/0223-5234(91)90070-4
• 作为产物：
  描述：

  3-脱氧尿苷 、 ammonium cerium (IV) nitrate 在 碘 作用下， 以 溶剂黄146 为溶剂， 生成 5-iodo-2'-deoxyuridine
  参考文献：
  名称：

  3'-Deoxyribonucleotide derivatives

  摘要：

  披露了由以下一般公式表示的3′-脱氧核苷酸衍生物：Q—V—(CH2)n—NH—R 其中 Q代表一个3′-脱氧核苷酸残基，n代表不小于4的整数，V代表—C≡C—或—CH═CH—，R代表一个荧光基团。上述3′-脱氧核苷酸衍生物是具有改善RNA聚合酶使用速率的衍生物，可用作DNA序列测定方法中利用RNA聚合酶的终止子。

  公开号：

  US06265569B1

文献信息

• [EN] COMPOSITIONS AND METHODS FOR SYNTHESIS OF PHOSPHORYLATED MOLECULES<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE SYNTHÈSE DE MOLÉCULES PHOSPHORYLÉES
  申请人：UNIV CALIFORNIA

  公开号：WO2019195494A1

  公开（公告）日：2019-10-10

  The invention provides compositions and methods for synthesis of phosphorylated organic compounds, including nucleoside triphosphates.

  这项发明提供了合成磷酸化有机化合物的组合物和方法，包括核苷三磷酸。
• Nucleotide mimics and their prodrugs
  申请人：——

  公开号：US20040059104A1

  公开（公告）日：2004-03-25

  The present invention relates to nucleoside diphosphate mimics and nucleoside triphosphate mimics, which contain diphosphate or triphosphate moiety mimics and optionally sugar-modifications and/or base-modifications. The nucleotide mimics of the present invention, in a form of a pharmaceutically acceptable salt, a pharmaceutically acceptable prodrug, or a pharmaceutical formulation, are useful as antiviral, antimicrobial, and anticancer agents. The present invention provides a method for the treatment of viral infections, microbial infections, and proliferative disorders. The present invention also relates to pharmaceutical compositions comprising the compounds of the present invention optionally in combination with other pharmaceutically active agents.

  本发明涉及核苷二磷酸模拟物和核苷三磷酸模拟物，其中包含二磷酸或三磷酸基团模拟物，以及可选的糖修饰和/或碱基修饰。本发明的核苷酸模拟物，以药学上可接受的盐、药学上可接受的前药或药物配方的形式，可用作抗病毒、抗微生物和抗癌剂。本发明提供了一种治疗病毒感染、微生物感染和增生性疾病的方法。本发明还涉及包含本发明化合物的药物组合物，可选地与其他药理活性剂结合。
• Modified nucleosides for the treatment of viral infections and abnormal cellular proliferation
  申请人：Gilead Pharmasset LLC

  公开号：US10100076B2

  公开（公告）日：2018-10-16

  The disclosed invention is a composition for and a method of seating a Flaviviridae (including BVDV and HCV), Orthomyxoviridae (including Influenza A and B) or Paramyxoviridae (including RSV) infection, or conditions related to abnormal cellular proliferation, in a host, including animals, and especially humans, using a nucleoside of general formula (I)-(XXIII) or its pharmaceutically acceptable salt or prodrug. This invention also provides an effective process to quantify the viral load, and in particular BVDV, HCV or West Nile Virus load, in a host, using real-time polymerase chain reaction (“RT-PCR”). Additionally, the invention discloses probe molecules that can fluoresce proportionally to the amount of virus present in a sample.

  所述的发明是关于一种用于在宿主中（包括动物，特别是人类）使用一般式（I）-（XXIII）的核苷或其药用可接受的盐或前药，对Flaviviridae（包括BVDV和HCV）、Orthomyxoviridae（包括流感A和B）或Paramyxoviridae（包括RSV）感染，或与异常细胞增殖相关的疾病进行座位的组合物和方法。该发明还提供了一种有效的过程，用于使用实时聚合酶链反应（“RT-PCR”）在宿主中定量病毒载量，特别是BVDV、HCV或西尼罗河病毒载量。此外，该发明还揭示了可以与样本中存在的病毒量成比例发出荧光的探针分子。
• Method of DNA sequencing
  申请人：The Institute of Physical and Chemical Research

  公开号：US06365350B1

  公开（公告）日：2002-04-02

  Disclosed are methods for determining DNA nucleotide sequences comprising reacting ribonucleoside 5′-triphosphates and 3′-dNTP derivatives in the presence of an RNA polymerase modified so as to enhance its ability for incorporating the 3′-dNTP derivatives and a DNA fragment containing a promoter sequence for the RNA polymerase to obtain a nucleic acid transcription product, separating the resulting nucleic acid transcription product, and determining a nucleic acid sequence from the resulting separated fraction. These methods can produce a transcription product of a long chain and afford more accurate sequence data where fluctuation of signals from labeled deoxyribonucleotides is reduced.

  揭示了一种确定DNA核苷酸序列的方法，包括在存在已经修改以增强其用于将3′-dNTP衍生物合并的RNA聚合酶的情况下，反应核苷酸5′-三磷酸酯和3′-dNTP衍生物，以及包含用于RNA聚合酶的启动子序列的DNA片段，以获得核酸转录产物，分离所得的核酸转录产物，并从分离的分数中确定核酸序列。这些方法可以产生长链的转录产物，并提供更准确的序列数据，减少了标记的脱氧核糖核苷酸信号波动。
• Enzyme catalyzed therapeutic compounds
  申请人：——

  公开号：US20040077588A1

  公开（公告）日：2004-04-22

  This invention provides novel substrate compounds that selectively inhibit the proliferation f path logical cells, for example, pathological cells that endogenously overexpress a target enzyme that confers resistance to biologic and chemotherapeutic agents. The enzyme acts on a substrate compound to 1) convert it to a cellular toxin and/or 2) release a toxic byproduct. In one embodiment, the activity of the target enzyme has been greatly enhanced in a target cell as a result of loss f tum r suppressor function and/or selection resulting from previous exposure to chemotherapy. In another embodiment, the pathological cell contains a target enzyme that is an expression product of an infectious agent in the cell. Further provided by this invention is a method for treating a subject by delivering to the subject a prodrug as described herein. The prodrugs f this invention may be used alone or in combination with ther chemotherapeutics or alternative anti-cancer therapies such as radiation.

  本发明提供了新型底物化合物，其选择性地抑制病理细胞的增殖，例如，内源性过度表达靶酶的病理细胞，该靶酶赋予生物和化学治疗药物抵抗力。该酶作用于底物化合物，以1）将其转化为细胞毒素和/或2）释放有毒副产物。在一种实施例中，由于肿瘤抑制因子功能的丧失和/或先前接受化疗的选择，靶细胞中的靶酶活性已被大大增强。在另一种实施例中，病理细胞包含一个靶酶，该靶酶是细胞内感染因子的表达产物。本发明还提供了一种通过向受试者输送如本文所述的前药来治疗受试者的方法。本发明的前药可以单独使用或与其他化疗药物或替代抗癌疗法（例如放疗）联合使用。