CAS: 69123-98-4; 1-((2R,3S,4R,5R)-3-Fluoro-4-Hydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-yl)-5-Iodopyrimidine-2,4(1H,3H)-Dione

该化合物是一个核素类比,主要在抗病毒研究中引起人们的兴趣,特别是它有可能用于对付乙型肝炎病毒,其特点是糖豆2号位置存在氟原子,这改变了它的生物活动,与天然核素相较,改变了它的生物活动;Fialuridine展示了一种行动机制,将它纳入病毒RNA或DNA,导致病毒复制的中断;其结构允许它模仿天然核糖酸,便利细胞吸收.然而,Fialoridine与严重的毒性有关,特别是肝中毒,限制了它的临床应用;该化合物通常在临床环境中研究,以更好地了解其药理特性,并探索更安全的衍生物或配方.总体而言,Fialoridinine是一个重要的例子,说明核素模拟的结构改变如何影响其治疗潜力和安全特征.

结构式图片

相似化合物

55612-21-0 784-71-4 69123-94-0

上下游产品

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合成工艺路线路线简述

  • 合成目标产物 Fialuridine 主要起始原料 3',5'-Di-O-Benzoyl Fialuridine
  • (文献来源)合成步骤主要原料 3',5'-Di-O-Benzoyl Fialuridine
2-脱氧-1-溴-2-氟-3,5-二苯甲酰基-Alpha-D-阿拉伯呋喃糖 以 甲醇,四氯化碳,氨 作为反应溶剂,化学反应 125.0H,反应生成 非阿尿苷
参考文献:Antiviral Nucleosides. A Stereospecific,Total Synthesis Of 2'-Fluoro-2'-Deoxy-.Beta.-D-Arabinofuranosyl Nucleosides
标题:Antiviral Nucleosides. A Stereospecific,Total Synthesis Of 2'-Fluoro-2'-Deoxy-.Beta.-D-Arabinofuranosyl Nucleosides
摘要:
DOI:10.1021/jo00236A017

海关参考信息

专利信息


专利号:US-10925977-B2
优先权日:2006-10-05
标 题 :Efficient synthesis of chelators for nuclear imaging and radiotherapy: compositions and applications
发明人:YANG DAVID J; YU DONGFANG; THOMPSON ANDREW S
权利人:YANG DAVID J; YU DONGFANG; THOMPSON ANDREW S; CEIL POINT LLC; UNIV TEXAS
摘要:Novel methods of synthesis of chelator-targeting ligand conjugates, compositions comprising such conjugates, and therapeutic and diagnostic applications of such conjugates are disclosed. The compositions include chelator-targeting ligand conjugates optionally chelated to one or more metal ions. Methods of synthesizing these compositions in high purity are also presented. Also disclosed are methods of imaging, treating and diagnosing disease in a subject using these novel compositions, such as methods of imaging a tumor within a subject and methods of diagnosing myocardial ischemia.

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-8912319-B2
优先权日:2010-07-15
标 题 :Synthesis of 2′-deoxy-2′-[18F]fluoro-5-methyl-1-B-D-arabinofuranosyluracil (18F-FMAU)
发明人:LI ZIBO; CAI HANCHENG; CONTI PETER S
权利人:LI ZIBO; CAI HANCHENG; CONTI PETER S; UNIV SOUTHERN CALIFORNIA
摘要:The present invention relates to methods of synthesizing 18 F-FMAU. In particular, 18 F-FMAU is synthesized using one-pot reaction conditions in the presence of Friedel-Crafts catalysts. The one-pot reaction conditions are incorporated into a fully automated cGMP-compliant radiosynthesis module, which results in a reduction in synthesis time and simplifies reaction conditions. The one-pot reaction conditions are also suitable for the production of 5-substituted thymidine or cytidine analogs. The products from the one-pot reaction (e.g. the labeled thymidine or cytidine analogs) can be used as probes for imaging tumor proliferative activity. More specifically, these [ 18 F]-labeled thymidine or cytidine analogs can be used as a PET tracer for certain medical conditions, including, but not limited to, cancer disease, autoimmunity inflammation, and bone marrow transplant.

专利号:US-2022233673-A1
优先权日:2019-06-04
标 题:METHODS OF PRODUCING SHIGA TOXIN B-SUBUNIT (STxB) MONOMERS AND OLIGOMERS, AND USES THEREOF
发明人:BILLET ANNE; SCHMIDT FRÉDÉRIC; JOHANNES LUDGER; SERVENT DENIS; MOURIER GILLES; TARTOUR ÉRIC; KAY MICHAEL; FULCHER JAMES M
权利人:INST CURIE; CENTRE NAT RECH SCIENT; INST NAT SANTE RECH MED; COMMISSARIAT A LENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES CEA; APHP ASSIST PUBLIQUE HOPITAUX DE PARIS; UNIV PARIS; UNIV OF UTAH RESEARCH FOUDATION; UNIV UTAH RES FOUND
摘要:A method of producing a monomer of a Shiga toxin B-subunit (STxB) protein or of a variant thereof by peptide chemical synthesis, as well as to a method of producing a pentamer of the STxB protein or of the variant thereof. The methods are particularly advantageous as they overcome major issues typically observed in peptide chemical synthesis, including solubility and purity issues.

专利号:US-5780617-A
优先权日:1990-05-29
标题 :Synthesis of liponucleotides
发明人:VAN DEN BOSCH HENK; VAN WIJK GYSBERT M T; KUMAR RAJ; HOSTETLER KARL Y
权利人:NEXSTAR PHARMACEUTICALS INC
摘要:A process for the preparation of glycerol di- or triphosphate derivatives comprising coupling the phosphate group of a glycerol monophosphate derivative in which one of the phosphate hydroxyls is replaced by a leaving group, with the terminal phosphate group of a mono- or diphosphate compound or a salt thereof, in the presence of a basic catalyst, under anhydrous conditions.

专利号:US-8147805-B2
优先权日:2005-01-05
标题:Conjugates for dual imaging and radiochemotherapy: composition, manufacturing, and applications
发明人:YANG DAVID; YU DONGFANG; CHANDA MITHU; AZHDARINIA ALI; OH CHANGSOK; KIM E EDMUND
权利人:YANG DAVID; YU DONGFANG; CHANDA MITHU; AZHDARINIA ALI; OH CHANGSOK; KIM E EDMUND; UNIV T EXAS SYSTEM BOARD OF REGENTS
摘要:Compositions and methods for dual imaging and for dual chemotherapy and radiotherapy are disclosed. More particularly, the invention concerns compounds comprising the structure X 1 —Y—X 2 , wherein Y comprises two or more carbohydrate residues covalently attached to one another, X 1 and X 2 are diagnostic or therapeutic moieties covalently attached to Y, provided that when Y does not comprise a glucosamine residue, X 1 and X 2 are diagnostic moieties. The present invention also concerns methods of synthesis of these compounds, application of such compounds for dual imaging and treatment of hyperproliferative disease, and kits for preparing a radiolabeled therapeutic or diagnostic compound.
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主要参考文献


1: Institute of Medicine (US) Committee to Review the Fialuridine (FIAU/FIAC) Clinical Trials; Manning FJ, Swartz M, editors. Review of the Fialuridine (FIAU) Clinical Trials. Washington (DC): National Academies Press (US); 1995. doi: 10.1371/journal.pmed.1001628.
3: Lee EW, Lai Y, Zhang H, Unadkat JD. Identification of the mitochondrial targeting signal of the human equilibrative nucleoside transporter 1 (hENT1): implications for interspecies differences in mitochondrial toxicity of fialuridine. J Biol Chem. 2006 Jun 16;281(24):16700-6. Review.
18: Ahluwalia GS, Driscoll JS, Ford H Jr, Johns DG. Comparison of the DNA incorporation in human MOLT-4 cells of two 2'-beta-fluoronucleosides, 2'-beta-fluoro-2',3'-dideoxyadenosine and fialuridine. J Pharm Sci. 1996 Apr;85(4):454-5. Review.

合成参考文献


摘要:New England Journal of Medicine., 333(1099), 1995 []
参考文献:10.1007/bf02738118
摘要:Perrino FW, Mazur DJ, Ward H, Harvey S. Exonucleases and the incorporation of aranucleotides into DNA. Cell Biochemistry and Biophysics. 1999 Oct;30(3):331–52. doi: 10.1007/bf02738118.
参考文献:10.1007/s13312-013-0199-5
摘要:Gandhoke I, Hussain SA, Pasha ST, Chauhan LS, Khare S. Glycoprotein B genotyping in congenital/perinatal Cytomegalovirus infection in symptomatic infants. Indian Pediatr. 2013 Jul;50(7):663–7. doi: 10.1007/s13312-013-0199-5.
参考文献:10.1007/s00261-017-1049-z
摘要:Jang JK, Jang HJ, Kim JS, Kim TK. Focal fat deposition in the liver: diagnostic challenges on imaging. Abdom Radiol (NY). 2017 Jun;42(6):1667–78. doi: 10.1007/s00261-017-1049-z.
参考文献:10.1007/978-1-0716-1601-7_11
摘要:Neyrinck K, García-León JA. Single Transcription Factor-Based Differentiation Allowing Fast and Efficient Oligodendrocyte Generation via SOX10 Overexpression. Methods Mol Biol. 2021;2352():149–70. doi: 10.1007/978-1-0716-1601-7_11.
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