CAS: 957-75-5; 5-Bromo-1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-yl)Pyrimidine-2,4(1H,3H)-Dione

该化合物是一种经过修改的核核素,其5个聚氨酯环的位置被一个溴原子所取代,这种卤化提高了其在生化和制药研究中的效用,特别是在涉及RNA结构和功能的研究中的效用.溴杂质有利于交叉连接实验,并充当X射线晶体学的重原子,有助于确定核酸的相容性.此外,5-Bromouridine由于能够破坏核酸代谢,因此被用作抗病毒剂和抗癌剂合成的前体.其稳定性和再活性使得它成为一种宝贵的工具,用于研究酶机制,设计基于核酸的治疗方法.

结构式图片

相似化合物

58-96-8 26287-69-4 3083-77-0

物理性质

MSDS等安全信息

上下游产品

CAS号58-96-8 尿苷 | CAS号105659-31-2 5-bromo-2',3',5... | CAS号4105-38-8 2,3,5-三乙酰尿苷 | CAS号13035-61-5 四乙酰核糖 | CAS号3066-86-2 5-溴胞苷 | CAS号2149-76-0 5-氨基尿苷盐酸盐 | CAS号58-96-8 尿苷 | CAS号19556-57-1 1-(β-D-ribofura... | CAS号957-77-7 5-羟基尿苷 | CAS号123131-51-1 6-hydroxyuridine | CAS号57901-65-2 9,5'-cyclo-3-(β... | CAS号55806-51-4 Uridine,5-(4-mo...

合成工艺路线路线简述

  • 合成目标产物 5-Bromouridine 主要起始原料 Guanosine
  • 105659-32-3 = 957-75-5
    反应条件:1.1 Catalysts: Sodium Methoxide Solvents: Methanol; 1 H,Rt
    标题:Ionic Liquid Mediated Synthesis Of 5-Halo-Uracil Nucleosides: Key Precursors For Potential Antiviral Drugs
    作者:Kumar,Vineet; Malhotra,Sanjay V.
    参考文献:Nucleosides 日期:2009 卷标:28(9) 页码:821-834]

    58-96-8 = 957-75-5
    反应条件:1.1 Reagents: N-Bromosuccinimide,Sodium Azide Solvents: 1,2-Dimethoxyethane
    标题:A Mild And Efficient Methodology For The Synthesis Of 5-Halogeno Uracil Nucleosides That Occurs Via A 5-Halogeno-6-Azido-5,6-Dihydro Intermediate
    作者:Kumar,Rakesh; Wiebe,Leonard I.; Knaus,Edward E.
    参考文献:Canadian Journal Of Chemistry 日期:1994 卷标:72(9) 页码:2005-10]

    58-96-8 = 957-75-5
    反应条件:1.1 Reagents: Sodium Azide,1,3,5-Triazine-2,4,6(1H,3H,5H)-Trione,1-Bromo-,Sodium Salt (1:1) Solvents: Acetonitrile,Water; 0.5 H,Rt
    标题:An Efficient And Facile Methodology For Bromination Of Pyrimidine And Purine Nucleosides With Sodium Monobromoisocyanurate (Smbi)
    作者:Maity,Jyotirmoy; Stromberg,Roger
    参考文献:Molecules 日期:2013 卷标:18(10) 页码:12740-12750]

    105659-32-3 = 957-75-5
    反应条件:1.1 Reagents: Ammonia Solvents: Methanol; Overnight,Rt
    标题:Triazole Pyrimidine Nucleosides As Inhibitors Of Ribonuclease A. Synthesis,Biochemical,And Structural Evaluation
    作者:Parmenopoulou,Vanessa; Chatzileontiadou,Demetra S. M.; Manta,Stella; Bougiatioti,Stamatina; Maragozidis,Panagiotis; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2012 卷标:20(24) 页码:7184-7193]

    58-96-8 = 957-75-5
    反应条件:1.1 Reagents: Bromine Solvents: Water; 10 Min,Heated; Rt
    标题:Microwave-Assisted Green Synthesis Of 5-Bromopyrimidine Derivatives
    作者:Qu,Gui-Rong; Han,Su-Hui; Zhang,Zhi-Guang; Geng,Ming-Wei; Xue,Feng
    参考文献:Henan Shifan Daxue Xuebao 日期:2006 卷标:34(2) 页码:65-67]

    58-96-8 = 957-75-5
    反应条件:1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide; Overnight,Rt
    标题:Lys314 Is A Nucleophile In Non-Classical Reactions Of Orotidine-5'-Monophosphate Decarboxylase
    作者:Heinrich,Daniel; Diederichsen,Ulf; Rudolph,Markus Georg
    参考文献:Chemistry - A European Journal 日期:2009 卷标:15(27) 页码:6619-6625]

    50-69-1 + 51-20-7 = 957-75-5 + 1809033-55-3
    反应条件:1.1 Reagents: 1,8-Diazabicyclo[5.4.0]Undec-7-Ene Solvents: Acetonitrile; 15 Min,Rt; Rt -> 0 °C1.2 Reagents: Tributylphosphine,Diisopropyl Azodicarboxylate; 5 Min,0 °C1.3 12 - 16 H,0 °C -> Rt1.4 Reagents: Hydrochloric Acid Solvents: Water; Neutralized
    标题:Direct One-Pot Synthesis Of Nucleosides From Unprotected Or 5-O-Monoprotected D-Ribose
    作者:Downey,A. Michael; Richter,Celin; Pohl,Radek; Mahrwald,Rainer; Hocek,Michal
    参考文献:Organic Letters 日期:2015 卷标:17(18) 页码:4604-4607]

    58-96-8 = 957-75-5
    反应条件:1.1 Reagents: N-Bromosuccinimide,Sodium Azide Solvents: 1,2-Dimethoxyethane; Rt
    标题:The Synthesis And Antituberculosis Activity Of 5-Alkynyl Uracil Derivatives
    作者:Platonova,Yana B.; Volov,Alexander N.; Tomilova,Larisa G.
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2020 卷标:30(16)]

    51-20-7 + 102916-66-5 = 957-75-5
    反应条件:1.1 Catalysts: Phosphoribomutase,Thymidine Phosphorylase Solvents: Water; 0.25 H,Ph 7,45 °C
    标题:Chemoenzymic Preparation Of Nucleosides From Furanoses
    作者:Taverna-Porro,Marisa; Bouvier,Leon A.; Pereira,Claudio A.; Montserrat,Javier M.; Iribarren,Adolfo M.
    参考文献:Tetrahedron Letters 日期:2008 卷标:49(16) 页码:2642-2645]

    58-96-8 = 957-75-5
    反应条件:1.1 Reagents: Bromine Solvents: Dimethylformamide
    标题:6-Cyano-1-β-D-Ribofuranosyluracil (6-Cyanouridine). Substitution Of An Unprotected Pyrimidine Nucleoside At Carbon Atom 6
    作者:Kalman,Thomas I.; Landesman,Paul W.
    参考文献:Nucleic Acid Chem. 日期:1991 卷标:4 页码:84-6]

    4105-38-8 = 957-75-5
    反应条件:1.1 Reagents: Lithium Bromide Solvents: Acetonitrile1.2 Reagents: Sodium Methoxide Solvents: Methanol
    标题:Cerium(Iv)-Mediated Halogenation At C-5 Of Uracil Derivatives
    作者:Asakura,Junichi; Robins,Morris J.
    参考文献:Journal Of Organic Chemistry 日期:1990 卷标:55(16) 页码:4928-33]

    58-96-8 = 957-75-5
    反应条件:1.1 Reagents: N-Bromosuccinimide Solvents: 1-Butyl-3-Methylimidazolium Trifluoroacetate; 5 H,25 °C1.2 Solvents: Methanol; 25 °C
    标题:Highly Efficient Method For C-5 Halogenation Of Pyrimidine-Based Nucleosides In Ionic Liquids
    作者:Kumar,Vineet; Yap,Jeremy; Muroyama,Andrew; Malhotra,Sanjay V.
    参考文献:Synthesis 日期:2009 卷标:(23) 页码:3957-3962]

    58-96-8 = 957-75-5
    反应条件:1.1 Reagents: N-Bromosuccinimide Solvents: Dimethyl Acetal; 5 Min,25 °C1.2 Reagents: Sodium Azide Solvents: Water; 2 H,Rt
    标题:Novel Derivatives Of Udp-Glucose: Concise Synthesis And Fluorescent Properties
    作者:Pesnot,Thomas; Wagner,Gerd K.
    参考文献:Organic & Biomolecular Chemistry 日期:2008 卷标:6(16) 页码:2884-2891]

    58-96-8 = 957-75-5
    反应条件:1.1 Reagents: 1,3-Dibromo-5,5-Dimethylhydantoin Solvents: Dimethylformamide; 20 Min,25 °C
    标题:Bromination At C-5 Of Pyrimidine And C-8 Of Purine Nucleosides With 1,3-Dibromo-5,5-Dimethylhydantoin
    作者:Rayala,Ramanjaneyulu; Wnuk,Stanislaw F.
    参考文献:Tetrahedron Letters 日期:2012 卷标:53(26) 页码:3333-3336]

    3263-91-0 = 957-75-5
    反应条件:1.1 Reagents: Ammonia Solvents: Methanol
    标题:Preparation Of Of 2-Hydroxyiminopyrimidine Nucleosides And Derivatives And Antiviral Uses Thereto
    参考文献:World Intellectual Property Organization]

    58-96-8 = 957-75-5
    反应条件:1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Dimethylformamide; 4 H,80 °C
    标题:Alternative Nucleic Acid Molecules And Uses Thereof
    参考文献:World Intellectual Property Organization]

    58-96-8 = 957-75-5
    反应条件:1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Dimethylformamide; 4 H,80 °C1.2 Reagents: Sodium Thiosulfate Solvents: Water
    标题:Preparation,Cytotoxicity,Apoptosis,And Transcription Of Modified Nucleic Acid Molecules And Uses Thereof
    参考文献:World Intellectual Property Organization
尿嘧啶核苷置于四丁基溴化铵,Lithium Bromide体系中,用 水,乙腈 作为反应溶剂,以43.1 %的收率获得产物5-溴尿苷
参考文献:使用 Libr 作为"br"源对富电子化合物进行电化学溴化
标题:使用 Libr 作为"br"源对富电子化合物进行电化学溴化
摘要:以libr为"br"源,在无过渡金属和无氧化剂的催化条件下,建立了一种直接电化学介导的富电子化合物ch溴化策略.该方法是在绿色且可持续的系统中进行的.人们发现多种富电子化合物是相容的,从而提供了具有中等产率的相应产物.
DOI:10.1016/j.Tetlet.2024.154927

海关参考信息

专利信息


专利号:US-2005130201-A1
优先权日:2003-10-14
标 题 :Splint-assisted enzymatic synthesis of polyribounucleotides
发明人：DERAS MICHAEL; PLEISS JEFFREY A; SCARINGE STEPHEN
权利人:DHARMACON INC
摘要:The present invention comprises methods and compositions for splint-assisted enzymatic synthesis of polyribonucleotides using an RNA polymerizing enzyme. The invention provides ligating ribonucleotides comprising ligating a donor RNA molecule to an acceptor RNA molecule in the presence of RNA ligase and a splint, wherein the donor RNA molecule is comprised of at least one nucleotide and a ligation linker moiety, the acceptor RNA molecule is comprised of at least one nucleotide and a ligation linker moiety and the splint is comprised of a polyribonucleotide. The invention also provides splints for use in splint-assisted enzymatic synthesis using an RNA polymerizing enzyme.

专利号:US-12146136-B2
优先权日:2020-03-26
标题:Synthesis of modified oligonucleotides with increased stability
发明人：KHVOROVA ANASTASIA; ROUX LOÃ?C MAURICE RENÉ JEAN; YAMADA KEN
权利人:UNIV MASSACHUSETTS
摘要:This disclosure relates to the synthesis of novel modified oligonucleotides. The synthesis of novel phosphoramidites are also provided.

专利号:US-11858953-B2
优先权日:2018-04-04
标 题:Compositions and methods for synthesis of phosphorylated molecules
发明人：CHAPUT JOHN; LIAO JEN-YU; BALA SAIKAT
权利人:UNIV CALIFORNIA
摘要:The invention provides compositions and methods for synthesis of phosphorylated organic compounds, including nucleoside triphosphates.

专利号:US-2012178710-A1
优先权日:2009-07-01
标题 :Synthesis of cyclic diguanosine monophosphate and thiophosphate analogs thereof
发明人：JONES ROGER A; GAFFNEY BARBARA L
权利人:JONES ROGER A; GAFFNEY BARBARA L; UNIV RUTGERS
摘要:The invention provides methods for the synthesis of cyclic dinucleotides and thiophosphate analogs thereof as well as a new family of analogs of cyclic diguanosine monophosphate that includes a series of seven phosphorothioate derivatives that includes diastereomers of mono-, di-, and trithiophosphates.

专利号:US-7777023-B2
优先权日:1998-10-23
标题 :Method for the chemical synthesis of oligonucleotides
发明人：VARGEESE CHANDRA; SHAFFER CHRISTOPHER; WANG WEIMIN
权利人:SIRNA THERAPEUTICS INC
摘要:The present invention features novel compositions, linkers, derivatized solid supports, and methods for the efficient solid phase synthesis of oligonucleotides, including RNA, DNA, RNA-DNA chimeras, and analogs thereof.

专利号:US-2023212204-A1
优先权日:2020-01-16
标题:Reagents and their use for modular enantiodivergent synthesis of c-p bonds
发明人：XU DONGMIN; RIVAS-BASCÓN NAZARET; KNOUSE KYLE W; PADIAL NATALIA; ZHENG BIN; VANTOUROUT JULIEN; SCHMIDT MICHAEL; EASTGATE MARTIN D; BARAN PHI
权利人:BRISTOL MYERS SQUIBB CO; SCRIPPS RESEARCH INST
摘要:The disclosure describes chiral P(V)-based reagents and their uses for the modular, scalable, and stereospecific synthesis of chiral phosphines, phosphine oxides and particular oligonucleotides.

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主要参考文献


1: Käppi R, Lönnberg H. Reactions of 5-bromo substituted pyrimidine nucleosides with aqueous alkalies: kinetics and mechanisms. Acta Chem Scand B. 1986 Oct;40(9):768-75. doi: 10.3891/acta.chem.scand.40b-0768.

合成参考文献


参考文献:10.1095/biolreprod.110.089474
摘要:Bui HT, Seo HJ, Park MR, Park JY, Thuan NV, Wakayama T, Kim JH. Histone deacetylase inhibition improves activation of ribosomal RNA genes and embryonic nucleolar reprogramming in cloned mouse embryos. Biol Reprod. 2011 Nov;85(5):1048–56. doi: 10.1095/biolreprod.110.089474.
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