CAS: 591-28-6; 4-Thioxo-3,4-Dihydropyrimidin-2(1H)-One

该化合物是一种含有硫的环环化合物,产自 uraciil, 其4 位置的氧原子被硫磺所取代.这种改变具有独特的化学特性,使其在生化和制药研究中具有价值.它作为核分子类比合成的关键中间体,广泛用于涉及RNA新陈代谢的研究,特别是作为RNA合成抑制剂.它的硫碳基集团在核分子替代反应中增强再活动性,促进其在标签和交叉连接应用中的效用.4-Thiouracil 由于其紫外线吸收特性,还用于光化化学研究.高纯度和稳定性确保实验环境中的连续性.

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35455-79-9 671-41-0 638-13-1

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上下游产品

CAS号3310-41-6 2-羟基-4-肼基嘧啶 | CAS号66-22-8 尿嘧啶 | CAS号35551-31-6 2(1H)-Pyrimidin... | CAS号74195-57-6 ethyl 2-[(2-oxo... | CAS号49844-94-2 1-methyl-4-(met... | CAS号49785-67-3 1,3-dimethyl-4-...

合成工艺路线路线简述

    尿嘧啶置于劳森试剂体系中,用 六甲基磷酰三胺 作为反应溶剂,化学反应 1.0H,以78%的收率获得产物4-硫尿嘧啶
    参考文献:Pyrimidine Derivatives; 1. The Highly Regioselective 4-Thionation Of Pyrimidine-2,4(1H,3H)-Dione Derivatives With Lawesson Reagent
    标题:Pyrimidine Derivatives; 1. The Highly Regioselective 4-Thionation Of Pyrimidine-2,4(1H,3H)-Dione Derivatives With Lawesson Reagent
    摘要:利用2,4-Bis(4-Methoxyphenyl)-2,4-Dithioxo-1,3,2,4-Dithiadiphosphetane(lawesson试剂),选择性地将5-氟尿嘧啶,尿嘧啶和胸腺嘧啶等嘧啶碱基的4-氧基转化为相应的4-硫代类似物.2-硫尿嘧啶也被转化为2,4-二硫尿嘧啶,但4-硫尿嘧啶几乎保持不变.
    DOI:10.1055/s-1988-27499

    海关参考信息

    专利信息


    专利号:US-12188072-B2
    优先权日:2018-03-19
    标题 :Compositions and methods for rapid in vitro synthesis of bioconjugate vaccines in vitro via production and N-glycosylation of protein carriers in detoxified prokaryotic cell lysates
    发明人:JEWETT MICHAEL CHRISTOPHER; STARK JESSICA CAROL; DELISA MATTHEW P; JAROENTOMEECHAI THAPAKORN
    权利人:UNIV NORTHWESTERN; UNIV CORNELL
    摘要:Disclosed are methods, systems, components, and compositions for cell-free synthesis of glycosylated carrier proteins. The glycosylated carrier proteins may be utilized in vaccines, including anti-bacterial vaccines. The glycosylated carrier proteins may include a bacterial polysaccharide conjugated to a carrier, which may be utilized to generate an immune response in an immunized host against the polysaccharide conjugated to the carrier. The glycosylated carrier proteins may be synthesized in cell-free glycoprotein synthesis (CFGpS) systems using prokaryote cell lysates that are enriched in components for glycoprotein synthesis such as oligosaccharyltransferases (OSTs) and lipid-linked oligosaccharides (LLOs) including OSTs and LLOs associated with synthesis of bacterial O antigens.

    专利号:US-12365930-B2
    优先权日:2016-07-14
    标题:Method for rapid in vitro synthesis of glycoproteins via recombinant production of N-glycosylated proteins in prokaryotic cell lysates
    发明人:JEWETT MICHAEL CHRISTOPHER; STARK JESSICA CAROL; DELISA MATTHEW P; JAROENTOMEECHAI THAPAKORN
    权利人:UNIV NORTHWESTERN; UNIV CORNELL
    摘要:Disclosed are methods, systems, components, and compositions for cell-free synthesis of glycosylated proteins. The glycosylated proteins may be utilized in vaccines, including anti-bacterial vaccines. The glycosylated proteins may include a bacterial polysaccharide conjugated to a carrier, which may be utilized to generate an immune response in an immunized host against the polysaccharide conjugated to the carrier. The glycosylated proteins may be synthesized in cell-free glycoprotein synthesis (CFGpS) systems using prokaryote cell lysates that are enriched in components for glycoprotein synthesis such as oligosaccharyltransferases (OSTs) and lipid-linked oligosaccharides (LLOs) including OSTs and LLOs associated with synthesis of bacterial O antigens.

    专利号:US-2024287520-A1
    优先权日:2021-06-30
    标题:Method for synthesis of linkage modified oligomeric compounds
    发明人:RODRIGUEZ ANDREW A
    权利人:IONIS PHARMACEUTICALS INC
    摘要:The present disclosure provides methods of synthesizing modified oligonucletodies and oligomeric compounds (including oligomeric compounds that are antisense agents or portions thereof) comprising a modified oligonucleotide having at least one modified internucleoside linking group. In certain embodiments, the present disclosure provides stabilized formulations of certain sulfonyl azides for use in the synthesis of olignonucleotides comprising one or more sulfonyl phosphoramidate linkages. Some embodiments provide stabilized compositions of high energy reagents that may be used in the synthesis of modified oligonucleotides, allowing for safe process scale preparation thereof.

    专利号:US-2004242897-A1
    优先权日:2002-07-31
    标题 :Universal support media for synthesis of oligomeric compounds
    发明人:GUZAEV ANDREI P; MANOHARAN MUTHIAH
    摘要:Compounds for the synthesis of oligomeric compounds, particularly oligonucleotides and oligonucleotide mimetics, are provided. In addition, methods for functionalizing a support medium with a first monomeric subunit and methods for the synthesis of oligomeric compounds utilizing the novel compounds bound to support media are provided.

    专利号:US-2024092821-A1
    优先权日:2020-03-31
    标题:Synthesis of oligonucleotides and related compounds
    发明人:ZHONG MINGHONG; JIN YI; GALA DINESH; PRHAVC MARIJA
    权利人:JANSSEN BIOPHARMA INC
    摘要:Methods of synthesizing oligonucleotides via new intermediates on a cleavable support having an azidomethyl moiety are disclosed. The method comprises multiple reaction cycles, each of which comprises sequential coupling a nucleoside or oligonucleotide subunit on a cleavable support having an azidomethyl moiety and a nucleoside phosphoramidite or an oligonucleotide phosphoramidite, capping, oxidation/thiolation and deblocking; followed by orthogonal cleavage of the azidomethyl support while keeping all other protecting groups intact. The method can be used in combination with a support moiety for either solid phase or liquid phase oligo synthesis. The soluble support facilitates homogeneous reactions and efficient separations by simple precipitation. The methods also provide novel intermediates useful in the synthesis of oligonucleotide conjugates.

    专利号:US-10751419-B2
    优先权日:2014-05-01
    标题:Method for synthesis of reactive conjugate clusters
    发明人:MIGAWA MICHAEL T; YU JINGHUA; WAN W BRAD; PATEL SAYTEN P; VASQUEZ GUILLERMO; KINBERGER GARTH A; PRAKASH THAZHA P; SETH PUNIT P; SWAYZE ERIC E
    权利人:IONIS PHARMACEUTICALS INC
    摘要:Provided herein are improved methods for the synthesis of reactive conjugate clusters and intermediates used in such methods. In particular, improvements are provided that enhance the synthesis of reactive conjugate clusters by reducing the number of synthetic steps required. The reactive conjugate clusters prepared using the improved methods don't include any transacylation impurities that are formed using existing methods. The improved methods also provide an increase in overall yield and a cost benefit over existing methods.
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    主要参考文献

    [参考文献]: A Psoda, Et Al. Structure And Tautomerism Of The Neutral And Monoanionic Forms Of 4-Thiouracil Derivatives. J Am Chem Soc. 1974 Oct 30;96(22):6832-9.
    [参考文献]: Artem Khvorostov, Et Al. Unimolecular Photochemistry Of 4-Thiouracils. Photochem Photobiol. 2005 Sep-Oct;81(5):1205-11.
    [参考文献]: Erik M Lenarcic, Et Al. Thiouracil Cross-Linking Mass Spectrometry: A Cell-Based Method To Identify Host Factors Involved In Viral Amplification. J Virol. 2013 Aug;87(15):8697-712.
    [参考文献]: Grazyna Wenska, Et Al. Mechanism And Dynamics Of Intramolecular Triplet State Decay Of 1-Propyl-4-Thiouracil And Its α-Methyl-Substituted Derivatives Studied In Perfluoro-1,3-Dimethylcyclohexane. Photochem Photobiol Sci. 2011 Aug;10(8):1294-302.
    [参考文献]: M Podar, Et Al. Photocrosslinking Of 4-Thio Uracil-Containing Rnas Supports A Side-By-Side Arrangement Of Domains 5 And 6 Of A Group Ii Intron. Rna. 1999 Feb;5(2):318-29.

    合成参考文献


    摘要:Mase, N., Science of Synthesis: Water in Organic Synthesis, (2012) 1, 191.
    参考文献:10.1007/978-1-59745-033-1_9
    摘要:Zeiner GM, Cleary MD, Fouts AE, Meiring CD, Mocarski ES, Boothroyd JC. RNA analysis by biosynthetic tagging using 4-thiouracil and uracil phosphoribosyltransferase. Methods Mol Biol. 2008;419():135–46. doi: 10.1007/978-1-59745-033-1_9.
    参考文献:10.1039/c1pp05034f
    摘要:Wenska G, Taras-Goślińska K, Łukaszewicz A, Burdziński G, Koput J, Maciejewski A. Mechanism and dynamics of intramolecular triplet state decay of 1-propyl-4-thiouracil and its α-methyl-substituted derivatives studied in perfluoro-1,3-dimethylcyclohexane. Photochemical & Photobiological Sciences. 2011 Aug;10(8):1294–302. doi: 10.1039/c1pp05034f.
    参考文献:10.1038/s41596-019-0179-x
    摘要:Matsushima W, Herzog VA, Neumann T, Gapp K, Zuber J, Ameres SL, Miska EA. Sequencing cell-type-specific transcriptomes with SLAM-ITseq. Nature Protocols. 2019 Jun 26;14(8):2261–78. doi: 10.1038/s41596-019-0179-x.
    参考文献:10.1385/1-59259-676-2:11
    摘要:Moore MJ. Joining RNA molecules with T4 DNA ligase. Methods Mol Biol. 1999;118():11–9. doi: 10.1385/1-59259-676-2:11.
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