CAS: 1024-99-3; 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-yl)-5-Iodopyrimidine-2,4(1H,3H)-Dione

该化合物是一种核素类比,其特征是,在尿利度分子的5个位置上存在碘原子,这种改变会影响其生物活动,特别是在抗病毒和抗癌症研究方面.化合物保留了尿利度的基本结构,它由与尿素基相连的肋骨糖组成,但碘替代可以加强其与核酸目标的相互作用.5-碘经常被研究其抑制病毒复制的潜力及其在各种生物化学途径中的作用.其溶性与稳定性可能不同,影响其药理和皮肤学及生物利用率.此外,碘的存在可能会产生独特的光谱特性,使其在某些分析技术中有用.

结构式图片

相似化合物

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

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

2',3',5'-tri-O-acetyl-5-iodouridine ethanol uridine Tri-O-acetyluridine 3-Methyl-2',3'-O-dimethyl-O6,5'-cyclouridinN3-Methyl-2',3'-O-dimethyl-O6,5'-cyclouridin methyl 3-(5-uridinyl)propenoate uridine(E)-5-2-(ethoxycarbonyl)vinyluridine uridine

合成工艺路线路线简述

    尿嘧啶核苷置于sodium Azide,一氯化碘体系中,用 乙腈 用作溶剂,化学反应 24.0H,以93%的收率获得5-碘尿苷
    参考文献:一种通过 5-Halogeno-6-Azido-5,6-Dihydro 中间体合成 5-Halogeno 尿嘧啶核苷的温和有效的方法
    标题:一种通过 5-Halogeno-6-Azido-5,6-Dihydro 中间体合成 5-Halogeno 尿嘧啶核苷的温和有效的方法
    摘要:已开发出一种温和有效的方法来合成 5-卤代(碘,溴或氯)尿嘧啶核苷.5-Halo-2'-Deoxyuridines 4A-c (84-95%),5-Halo-Arabinouridines 7A-c (45-95%),And 5-Haloarabinouridines 8A-c (65-95%) 合成非常好2'-脱氧尿苷 (2),尿苷 (5) 和阿拉伯尿苷 (6) 分别与一氯化碘或 N-溴(或氯)琥珀酰亚胺和叠氮化钠在 25-45 oc 下反应生成.这些 C-5 卤化反应通过 5-卤代-6-叠氮基-5,6-二氢中间体 (3) 进行,从中消除 Hn3,反应生成5-卤代尿嘧啶核苷.5-Halo-6-Azido-5,6-Dihydro 中间产物 (10A,10B) 可以从 3',5'-Di-O-Acetyl-2'-Deoxyuridine (9) 与一氯化碘的反应中分离出来或 N-溴代琥珀酰亚胺和叠氮化钠在
    Doi:10.1139/v94-256

    海关参考信息

    专利信息


    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-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.

    专利号:US-2024384319-A1
    优先权日:2021-09-17
    标题 :Synthesis of Oligonucleotides
    发明人:LOVELOCK SARAH
    权利人:UNIV MANCHESTER
    摘要:The present invention relates to a novel method for oligonucleotide synthesis, using a catalytic primer-template, e.g. a hairpin primer, to achieve multiple rounds of oligonucleotide synthesis and dissociation from the template in the same reaction, such that at the end of the reaction the amount of oligonucleotide generated is greater than the amount of template provided in the reaction. The primer contains a cleavable site and the reaction is carried out in a single mixture with a cleavage agent. The cleavable site may be an inosine and the agent an endonuclease V.

    专利号:US-2014378538-A1
    优先权日:2011-12-14
    标 题:Methods of responding to a biothreat
    发明人:BANCEL STEPHANE
    权利人:MODERMA THERAPEUTICS INC
    摘要:The present disclosure provides for devices, in particular mobile devices, which may be used in the synthesis of modified nucleic acid molecules, in particular modified mRNA molecules. The device for making the modified nucleosides, modified nucleotides and modified nucleic acids (e.g., mRNA) disclosed herein may be mobile devices comprising at least one sample block for insertion of one or more sample vessels, a device base with electronic control units for the sample block, a voltage supply, and one or more reagent(s) for the synthesis of at least one nucleic acid.
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    主要参考文献

    [参考文献]: Robak T, Robak P. Purine Nucleoside Analogs In The Treatment Of Rarer Chronic Lymphoid Leukemias. Curr Pharm Des. 2012;18(23):3373-88.
    [参考文献]: B L Golden, Et Al. X-Ray Crystallography Of Large Rnas: Heavy-Atom Derivatives By Rna Engineering. Rna. 1996 Dec;2(12):1295-305.
    [参考文献]: Daniel E Ryan, Et Al. New Tertiary Constraints Between The Rna Components Of Active Yeast Spliceosomes: A Photo-Crosslinking Study. Rna. 2004 Aug;10(8):1251-65.
    [参考文献]: K Shah, Et Al. Synthesis Of Uridine Phosphoramidite Analogs: Reagents For Site-Specific Incorporation Of Photoreactive Sites Into Rna Sequences. Bioconjug Chem. 1994 Nov-Dec;5(6):508-12.
    [参考文献]: Loc Ropartz, Et Al. Phosphine Containing Oligonucleotides For The Development Of Metallodeoxyribozymes. Chem Commun (Camb). 2007 Apr 21:(15):1556-8.

    合成参考文献


    摘要:K. Berens and D. Shugar, Acta Biochim. Pol. 10, 25 (1963).
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