tert-butyl (5-iodouracil-1-yl)acetate | 207724-94-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (5-iodouracil-1-yl)acetate
• 英文别名: N¹-(tert-butoxycarbonylmethyl)-5-iodouracil；1-tert-butyloxycarbonylmethyl-5-iodouracil；t-butyl (5-iodouracil-1-yl)acetate；Tert-butyl 2-(5-iodo-2,4-dioxopyrimidin-1-yl)acetate
• CAS: 207724-94-5
• 化学式: C₁₀H₁₃IN₂O₄
• 分子量: 352.129
• InChiKey: GYLILQXIKLSUKW-UHFFFAOYSA-N

物化性质

• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (5-iodouracil-1-yl)acetate 在 copper(l) iodide 、 四(三苯基膦)钯 、 甲酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  5-(Perylen-3-ylethynyl)uracil 作为抗病毒支架：3-甲基衍生物在体外对包膜病毒繁殖的有效抑制

  摘要：

  五环芳烃苝的两亲性核苷和非核苷衍生物被称为有效的非细胞毒性广谱抗病毒药。在这里，我们报告了 3-methyl-5-(perylen-3-ylethynyl)-uracil-1-acetic acid 及其酰胺，这是基于 5-(perylen-3-ylethynyl)-uracil 支架的一系列新化合物。这些化合物在体外对节肢动物传播的病毒，即蜱传脑炎病毒 (TBEV) 和黄热病病毒 (YFV)，在斑块减少试验中表现出显着的活性，EC 50值分别低于 1.9 和 1.3 nM，以及基孔肯雅病毒 ( CHIKV) 在用 EC 50进行的细胞病变效应抑制试验中值低于 3.2 μM。这些化合物对呼吸道病毒也有活性：细胞病变效应抑制试验中的严重急性呼吸系统综合症相关冠状病毒 2 (SARS-CoV-2) 和病毒滴度降低实验中的甲型流感病毒 (IAV) 均受到抑制 – EC 50值低于 51分别为 nM

  DOI：

  10.1016/j.antiviral.2022.105508
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 5-碘尿嘧啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.17h， 以86%的产率得到tert-butyl (5-iodouracil-1-yl)acetate
  参考文献：
  名称：

  [EN] MODIFIED THYMINE POLYNUCLEOTIDE OLIGOMERS AND METHODS
  [FR] OLIGOMÈRES POLYNUCLÉOTIDIQUES À BASES THYMINE MODIFIÉES ET PROCÉDÉS ASSOCIÉS

  摘要：

  本文披露了一种改良的胸腺嘧啶碱基，可提供对腺嘌呤或2,6-二氨基嘌呤碱基在多核苷酸杂交复合物中的增强碱基配对亲和性。还披露了多核苷酸寡聚体、包含这种改良胸腺嘧啶碱基的多核苷酸杂交复合物。还披露了各种使用方法。例如，在某些实施方式中，本文披露的改良多核苷酸寡聚体可用作核酸扩增和/或检测的引物和探针。

  公开号：

  WO2015153496A1

文献信息

• Synthesis of A Fluorescent PNA Monomer Containing 5-((9<b> <i>H</i> </b>-Fluoren-2-YL)Ethynyl)Uracil
  作者：Filip Wojciechowski、Robert H. E. Hudson

  DOI：10.1080/15257770701527802

  日期：2007.11.26

  modified nucleobases in order to further improve their fluorescence response, increase their aqueous solubility and stabilize hybrids formed with complementary nucleic acids. As an example of this work, we have synthesized the 5-((9 H-fluoren-2-yl)ethynyl)uracil PNA monomer that will be incorporated into oligomers using Fmoc-based chemistry. Initial evaluation of the fluorescence of the 5-((9 H-flu

  带有 5-苯基乙炔基取代的嘧啶核碱基代表紧凑且固有荧光的核碱基。这样的核碱基能够选择性识别互补碱基并且可以荧光报告杂交事件。我们过去的工作表明，5-苯基乙炔基尿嘧啶的荧光对苯环上的取代很敏感，但这些是相对较弱的荧光团。我们目前正在对这些修饰的核碱基的苯基进行功能化，以进一步改善它们的荧光响应，增加它们的水溶性并稳定与互补核酸形成的杂交体。作为这项工作的一个例子，我们合成了 5-((9 H-芴-2-基) 乙炔基) 尿嘧啶 PNA 单体，该单体将使用基于 Fmoc 的化学结合到低聚物中。
• C(5) modified uracil derivatives showing antiproliferative and erythroid differentiation inducing activities on human chronic myelogenous leukemia K562 cells
  作者：Eleonora Brognara、Ilaria Lampronti、Giulia Breveglieri、Alessandro Accetta、Roberto Corradini、Alex Manicardi、Monica Borgatti、Alessandro Canella、Chiara Multineddu、Rosangela Marchelli、Roberto Gambari

  DOI：10.1016/j.ejphar.2011.09.024

  日期：2011.12

  The K562 cell line has been proposed as a useful experimental system to identify anti-tumor compounds acting by inducing terminal erythroid differentiation. K562 cells exhibit a low proportion of hemoglobin-synthesizing cells under standard cell growth conditions, but are able to undergo terminal erythroid differentiation when treated with a variety of anti-tumor compounds. In this paper we report a screening study on a set of different modified C(5) uracil derivatives for the evaluation of their antiproliferative effect in connection with erythroid differentiation pathways, and for defining a new class of drug candidates for the treatment of chronic myelogenous leukemia. Activity of the derivatives tested can be classified in two effect: an antiproliferative effect linked to a high level of erythroid differentiation activity and an antiproliferative effect without activation of gamma globin genes The highest antiproliferative effect and erythroid induction was shown by compound 9, a thymine derivative bearing a n-octyl chain on nitrogen N(1), whereas thymine did not show any effect, suggesting the importance of the linear alkyl chain in position N(1). To our knowledge this compound should be considered among the most efficient inducers of erythroid differentiation of K562 cells. This work is the starting point for the quest of more effective and specific drugs for the induction of terminal erythroid differentiation, for leading new insights in the treatment of neoplastic diseases with molecules acting by inducing differentiation rather than by simply exerting cytotoxic effects. (C) 2011 Elsevier B.V. All rights reserved.
• Compounds based on 5-(perylen-3-ylethynyl)uracil scaffold: High activity against tick-borne encephalitis virus and non-specific activity against enterovirus A
  作者：Alexey A. Chistov、Alexey A. Orlov、Philipp P. Streshnev、Nikita A. Slesarchuk、Ilya O. Aparin、Brijesh Rathi、Vladimir A. Brylev、Sergey V. Kutyakov、Irina V. Mikhura、Alexey V. Ustinov、Gunnar Westman、Vladimir A. Palyulin、Nidhi Jain、Dmitry I. Osolodkin、Liubov I. Kozlovskaya、Vladimir A. Korshun

  DOI：10.1016/j.ejmech.2019.03.029

  日期：2019.6

  Rigid amphipathic fusion inhibitors (RAFIs) are potent antivirals based on a perylene core linked with a nucleoside moiety. Sugar-free analogues of RAFIs, 5-(perylen-3-ylethynyl)uracil-1-acetic acid 1 and its amides 2, were synthesized using combined protection group strategy. Compounds 1 and 2 appeared to have low toxicity on porcine embryo kidney (PEK) or rhabdomiosarcoma (RD) cells together with remarkable activity against enveloped tick-borne encephalitis virus (TBEV): EC50 values vary from 0.077 mu M to subnanomolar range. Surprisingly, 3-pivaloyloxymethyl (Pom) protected precursors 7 and 8 showed even more pronounced activity. All the compounds showed no activity against several non enveloped enteroviruses, except 4-hydroxybutylamides 2d,g, which inhibited the reproduction of enterovirus A71 with EC50 50-100 mu M, with a non-specific mode of action. The results suggest that the carbohydrate moiety of RAFI nucleosides does not play a crucial role in their antiviral action, and biological activity of the 5-(perylen-3-ylethynyl)uracil scaffold can be effectively modulated by substituents in positions 1 and 3. The high antiviral activity of these new compounds, coupled with low toxicity advocate their potential role in antiviral therapy. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Synthesis and characterization of cationic PNA bearing 5-ω-aminopropyl-uracil
  作者：Paul H. Kim、Christopher Switzer

  DOI：10.1016/j.tetlet.2014.08.029

  日期：2014.10

  5-omega-Aminopropyl-uracil bearing PNA monomers are synthesized for solid phase oligomer synthesis using FMOC protection. Several PNA oligomers with differing amounts of aminopropyluracil modification were prepared. These oligomers were found to associate with complementary DNA oligonucleotides. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of Fluorine-Labeled Peptide Nucleic Acid Building Blocks as Sensors for the ¹⁹F NMR Spectroscopic Detection of Different Hybridization Modes
  作者：Anu Kiviniemi、Merita Murtola、Petri Ingman、Pasi Virta

  DOI：10.1021/jo400014y

  日期：2013.6.7

  Peptide nucleic acid (PNA) building blocks, bearing a fluorine sensor at C-5 of the uracil base [viz. trifluoromethyl and 3,3-bis(trifluoromethyl)-4,4,4-trifluorobut-1-ynyl], were synthesized and incorporated to a PNA strand, and their applicability for the monitoring of different hybridization modes by F-19 NMR spectroscopy was studied. Both sensors gave unique F-19 resonance shifts in NMR when the PNA was targeted to a complementary antiparallel DNA, antiparallel RNA, parallel DNA, and parallel RNA. The 5-trifluoromethyl-derived sensor was additionally applied for the monitoring of interconversions from a parallel DNA/PNA complex to an antiparallel RNA/PNA complex and from a PNA/PNA complex to two DNA/PNA complexes (i.e., double-duplex invasion).