CAS: 85-31-4; 6-Thioguanosine

该化合物是一种核肺类比,其特点是与糖相连的谷氨基,其硫磺原子取代了的氧气.这种改变使硫酸盐具有独特的化学特性,使其成为生化研究和治疗应用中的一个重要化合物.已知它参与了各种生物化学途径,特别是在核酸代谢和细胞信号方面.硫酸可被磷化成三磷酸(TGTP),然后可以纳入RNA,从而可能影响RNA的稳定性和功能.复合物表现出抗甲酸特性,可以干扰DNA和RNA合成,从而引起对癌症治疗和细胞扩散问题的其他疾病的兴趣.此外,硫酸在结构上与天然核糖相类似,允许其在生物系统中模拟其行为,提供对核糖相互作用和功能的洞察.其化学文号(85-31-4)是其独特的识别资料库和化学文献库,便于识别.

结构式图片

相似化合物

574-25-4 789-61-7 345909-25-3

物理性质

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CAS号4546-54-7 2-氨基嘌呤核苷

合成工艺路线路线简述

  • 合成目标产物 6-Thioguanosine 主要起始原料 Guanosine 2',3',5'-Tribenzoate
  • 2946-36-3 = 85-31-4
    反应条件:1.1 Reagents: Sodium Methoxide Solvents: Methanol
    标题:Thiosulfate Method Of Synthesizing 6-Thioguanine And 6-Thioguanosine
    作者:Calmane,L.; Et Al
    参考文献:Khimiko-Farmatsevticheskii Zhurnal 日期:1989 卷标:23(9) 页码:1129-31]

    13035-61-5 + 830330-45-5 = 85-31-4 [标题:Reaction Conditions
    标题:Product Class 17: Purines
    作者:Seela,F.; Et Al
    参考文献:Science Of Synthesis 日期:2004 卷标:16 页码:945-1108]

    71-91-0 = 85-31-4
    反应条件:1.1 Reagents: Zinc Chloride Solvents: Dimethylformamide1.2 Reagents: Ethylenediaminetetraacetic Acid,Sodium Bicarbonate Solvents: Water1.3 -2.1 Reagents: Sodium Perchlorate Solvents: Acetone,Water
    标题:Cap Analogs Containing 6-Thioguanosine - Reagents For The Synthesis Of Mrnas Selectively Photo-Crosslinkable With Cap-Binding Biomolecules
    作者:Nowakowska,Monika; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2014 卷标:12(27) 页码:4841-4847]

    532-55-8 = 85-31-4 [标题:Reaction Conditions
    标题:Product Class 17: Purines
    作者:Seela,F.; Et Al
    参考文献:Science Of Synthesis 日期:2004 卷标:16 页码:945-1108]

    30747-23-0 + 86357-13-3 = 85-31-4 [标题:Reaction Conditions
    标题:Product Class 17: Purines
    作者:Seela,F.; Et Al
    参考文献:Science Of Synthesis 日期:2004 卷标:16 页码:945-1108]

    58-96-8 + 154-42-7 = 85-31-4
    反应条件:1.1 Solvents: Water; 1 H,Ph 7,60 °C
    标题:Aeromonas Hydrophila Strains As Biocatalysts For Transglycosylation
    作者:Nobile,Matias; Et Al
    参考文献:Biocatalysis And Biotransformation 日期:2011 卷标:28(5-6) 页码:395-402]

    58-96-8 + 154-42-7 = 85-31-4
    反应条件:1.1 Solvents: Water; 5 H,Ph 7,60 °C
    标题:Arthrobacter Oxydans As A Biocatalyst For Purine Deamination
    作者:Medici,Rosario; Et Al
    参考文献:Fems Microbiology Letters 日期:2008 卷标:289(1) 页码:20-26]

    16321-99-6 = 85-31-4
    反应条件:1.1 Reagents: Sodium Thiosulfate Solvents: Ethanol
    标题:Sodium Thiosulfate And Potassium Selenosulfate As Reagents To Prepare Thio- And Selenopurine Nucleosides
    作者:Jankowski,Aleksander J.; Et Al
    参考文献:Nucleosides & Nucleotides 日期:1989 卷标:8(3) 页码:339-48]

    16321-99-6 = 85-31-4
    反应条件:1.1 Reagents: Sodium Thiosulfate Solvents: Water2.1 Reagents: Sodium Methoxide Solvents: Methanol
    标题:Thiosulfate Method Of Synthesizing 6-Thioguanine And 6-Thioguanosine
    作者:Calmane,L.; Et Al
    参考文献:Khimiko-Farmatsevticheskii Zhurnal 日期:1989 卷标:23(9) 页码:1129-31]

    2004-07-1 = 85-31-4
    反应条件:1.1 Reagents: Sodium Thiosulfate Solvents: Ethanol,Water
    标题:Sodium Thiosulfate And Potassium Selenosulfate As Reagents To Prepare Thio- And Selenopurine Nucleosides
    作者:Jankowski,Aleksander J.; Et Al
    参考文献:Nucleosides & Nucleotides 日期:1989 卷标:8(3) 页码:339-48]

    961-07-9 = 85-31-4
    反应条件:1.1 Reagents: Pyridine,Trifluoroacetic Anhydride Solvents: Pyridine1.2 Reagents: Sodium Hydrosulfide Solvents: Dimethylformamide
    标题:One-Flask Syntheses Of 6-Thioguanosine And 2'-Deoxy-6-Thioguanosine
    作者:Kung,Pei Pei; Et Al
    参考文献:Tetrahedron Letters 日期:1991 卷标:32(32) 页码:3919-22]

    = 85-31-4
    反应条件:1.1 Reagents: Sodium Perchlorate Solvents: Acetone,Water
    标题:Cap Analogs Containing 6-Thioguanosine - Reagents For The Synthesis Of Mrnas Selectively Photo-Crosslinkable With Cap-Binding Biomolecules
    作者:Nowakowska,Monika; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2014 卷标:12(27) 页码:4841-4847]

    118-00-3 = 85-31-4 [标题:Reaction Conditions
    标题:Product Class 17: Purines
    作者:Seela,F.; Et Al
    参考文献:Science Of Synthesis 日期:2004 卷标:16 页码:945-1108]

    133068-54-9 = 85-31-4 [标题:Reaction Conditions
    标题:Product Class 17: Purines
    作者:Seela,F.; Et Al
    参考文献:Science Of Synthesis 日期:2004 卷标:16 页码:945-1108]

    6974-32-9 + 19962-37-9 = 85-31-4 [标题:Reaction Conditions
    标题:Product Class 17: Purines
    作者:Seela,F.; Et Al
    参考文献:Science Of Synthesis 日期:2004 卷标:16 页码:945-1108]

    288-32-4 + 15867-02-4 = 85-31-4
    反应条件:1.1 Reagents: Triethylamine,Triphenylphosphine,2,2′-Dipyridyl Disulfide Solvents: Dimethylformamide; 6 - 8 H,Rt1.2 Reagents: Lithium Perchlorate Solvents: Acetone; Rt2.1 Reagents: Zinc Chloride Solvents: Dimethylformamide2.2 Reagents: Ethylenediaminetetraacetic Acid,Sodium Bicarbonate Solvents: Water2.3 -3.1 Reagents: Sodium Perchlorate Solvents: Acetone,Water
    标题:Cap Analogs Containing 6-Thioguanosine - Reagents For The Synthesis Of Mrnas Selectively Photo-Crosslinkable With Cap-Binding Biomolecules
    作者:Nowakowska,Monika; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2014 卷标:12(27) 页码:4841-4847
📜鸟苷 2',3',5'-三苯甲酸酯置于吡啶,Tetraphosphorus Decasulfide,Sodium Ethanolate体系中,化学反应生成 6-巯基鸟嘌呤核苷
参考文献:Thiation Of Nucleosides. I. Synthesis Of 2-Amino-6-Mercapto-9-β-D-Ribofuranosylpurine ("thioguanosine") And Related Purine Nucleosides1
标题:Thiation Of Nucleosides. I. Synthesis Of 2-Amino-6-Mercapto-9-β-D-Ribofuranosylpurine ("thioguanosine") And Related Purine Nucleosides1
摘要:
DOI:10.1021/ja01540A041

海关参考信息

专利信息


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-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.

专利号:US-2005080260-A1
优先权日:2003-04-22
标 题 :Preparation of prodrugs for selective drug delivery
发明人：MILLS RANDELL L; WU GUO-ZHANG
摘要:Synthesis of a chemical compound having the formula A-B-C that may serve for applications such as drug delivery where A is a chemiluminescent, moiety, B is a photochromic moiety, and C is a biologically active moiety where A-B-C may serve as a prodrug. Novel synthetic methods of the present invention to form the prodrug comprised the steps of (1) forming a benzophenone, (2) forming a diaryl ethylene, (3) attaching a phthalimide moiety to at least one of the aryl groups of the ethylene to form a phthalimide-ethylene conjugate, (4) condensing two ethylene-phthalimide conjugates to form a phthalimide-pentadiene conjugate, (5) converting the phthalimide to the phthalhydrazide by reaction with hydrazine to form a carrier compound according to the present invention, and (6) reacting the carrier compound with an nucleophilic moiety of the drug to form the corresponding prodrug. Alternatively the carrier can be prepared by using the halo-substituted diaryl ethylene to make the corresponding cationic leuco dye-like compound with known methods. The cationic compound then is protected by reacting with a nucleophile and coupled with the aminophathalimide by palladium-catalyzed amination to form the protected phthalimide-pentadiene conjugate. The latter is refluxed with hydrazine to convert its phthalimide to the phthalhydrazide and acidified to give the carrier. An additional aspect of the present invention relates to the use of these compounds as antiviral agents for the treatment of viral infections such as HIV and as anticancer agents for the treatment of cancers such as bowel, lung, and breast cancer.

专利号:US-9790531-B2
优先权日:2012-08-14
标 题 :Enzymes and polymerases for the synthesis of RNA
发明人：WANG YUXUN; RAMAKRISHNAN DIVAKAR; DE FOUGEROLLES ANTONIN; WHORISKEY SUSAN
权利人:MODERNATX INC
摘要:The invention relates to compositions and methods for the design, evolution, preparation, and/or manufacture of enzymes for use with polynucleotides, primary transcripts and mmRNA molecules.

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主要参考文献


1: Inde T, Nishizawa S, Hattori Y, Kanamori T, Yuasa H, Seio K, Sekine M, Ohkubo A. Synthesis of and triplex formation in oligonucleotides containing 2'-deoxy-6-thioxanthosine. Bioorg Med Chem. 2018 Jun 5. pii: S0968-0896(18)30902-7. doi: 10.1016/j.bmc.2018.06.004. [Epub ahead of print] pii: E18. doi: 10.3390/scipharm86020018.
3: Miyata S, Yamada T, Isozaki T, Sugimura H, Xu YZ, Suzuki T. Absorption Characteristics and Quantum Yields of Singlet Oxygen Generation of Thioguanosine Derivatives. Photochem Photobiol. 2018 Jul;94(4):677-684. doi: 10.1111/php.12900. Epub 2018 Mar 31. doi: 10.1039/c7fd00193b. doi: 10.1021/jacs.7b08755. Epub 2017 Nov 22.
6: Al-Mahamad LLG, El-Zubir O, Smith DG, Horrocks BR, Houlton A. A coordination polymer for the site-specific integration of semiconducting sequences into DNA-based materials. Nat Commun. 2017 Sep 28;8(1):720. doi: 10.1038/s41467-017-00852-6.

合成参考文献


摘要:Advances in Teratology., 3(181), 1968
摘要:National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program., JAN1986
摘要:Progress in Medical Chemistry., 7(69), 1970 []
参考文献:10.1007/978-1-4939-3067-8_12
摘要:Jens M. A Pipeline for PAR-CLIP Data Analysis. Methods Mol Biol. 2016;1358():197–207. doi: 10.1007/978-1-4939-3067-8_12.
参考文献:10.1186/s12977-018-0417-2
摘要:Bieniasz PD, Kutluay SB. CLIP-related methodologies and their application to retrovirology. Retrovirology. 2018 May 02;15(1):35.
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