CAS: 69-33-0; 4-Amino-7-(ß-D-Ribofuranosyl)Pyrrolo[2,3-D]Pyrimidine

该化合物是一种以其对RNA和DNA合成的强效抑制作用而闻名的核核素抗生素和腺素类比,具有竞争力地将其纳入核酸,干扰复制和转录过程,使其成为生化和微生物研究的宝贵工具.Tubercidin展示了针对细菌,真菌和原生动物的广泛活动,并被用于纯新陈代谢和核酸功能的研究.其行动机制也与肿瘤学和病毒学调查相关.该化合物的特点是稳定性和特性,能够进行精确的实验性应用.适当的处理由于其生物活性,至关重要.

结构式图片

相似化合物

443642-29-3 24386-93-4 60129-59-1

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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 Tubercidin 主要起始原料 4-Chloro-7-(2,3,5-Tri-O-Benzoyl-β-D-Ribofuranosyl)-7H-Pyrrolo[2,3-D]Pyrimidine
  • (文献来源)合成步骤主要原料 4-Chloro-7-(2,3,5-Tri-O-Benzoyl-β-D-Ribofuranosyl)-7H-Pyrrolo[2,3-D]Pyrimidine
5-溴杀结核菌素置于palladium On Activated Charcoal,甲酸铵体系中,用 乙醇 作为反应溶剂,化学反应 3.0H,以65%的收率获得产物杀结核菌素
参考文献:吡咯并[2,3-D]嘧啶与1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖的糖基化作用:取代基和保护基团,影响7-脱氮嘌呤核糖核苷的合成
标题:吡咯并[2,3-D]嘧啶与1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖的糖基化作用:取代基和保护基团,影响7-脱氮嘌呤核糖核苷的合成
摘要:非官能化的6-氯-7-脱氮嘌呤与市售的1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖(45%)进行糖基化,然后胺化和脱保护,仅得到两种形式的结核菌素脚步.应用类似的条件,采用吡咯烷基化的2-氨基-6-氯-7-脱氮嘌呤合成7-脱氮鸟嘌呤,可以得到18%的糖基化产率.较小体积的异丁酰基或乙酰基保护的氨基将糖基化指向环外氨基取代基.将7-卤代中间体糖基化,然后脱卤以克服7-脱氮鸟苷合成中低糖基化产率.
DOI:10.1021/acs.Joc.8B00343

海关参考信息

专利信息


专利号:US-6048975-A
优先权日:1991-09-12
标 题:Process for the chemical synthesis of oligonucleotides
发明人:PFLEIDERER WOLFGANG; BERGMANN FRANK
权利人:HOECHST AG
摘要:A process for the chemical synthesis of oligonucleotides n Use of a dansylethoxycarbonyl group as base-labile 5'-hydroxyl protective group in the chemical synthesis of DNA and RNA and suitable synthetic processes. n The ease of detection of the dansyl protective group and the ease of elimination from the sugar residue of the nucleotide without side reactions make oligonucleotide synthesis possible with high yields in very small quantities.

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-5945524-A
优先权日:1990-09-14
标 题 :Process for the chemical synthesis of oligonucleotides
发明人:PFLEIDERER WOLFGANG; BERGMANN FRANK
权利人:HOECHST AG
摘要:Use of a dansylethoxycarbonyl group as base-labile 5'-hydroxyl protective group in the chemical synthesis of DNA and RNA and suitable synthetic processes. n The ease of detection of the dansyl protective group and the ease of elimination from the sugar residue of the nucleotide without side reactions make oligonucleotide synthesis possible with high yields in very small quantities.

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-7122693-B2
优先权日:1988-04-11
标题 :Acetaldehyde acetal compounds, their synthesis, and uses thereof
发明人:BELLEAU EXECUTRIX OF ESTATE PI; DIXIT DILIP M; NGUYEN-BA NGHE
权利人:SHIRE BIOCHEM INC
摘要:The acetaldehyde compounds, 2-thiobenzoylacetaldehyde diethylacetal, 2-benzoyloxyacetaldehyde bis(2-methoxyethyl)acetal, 2-hydroxyacetaldehyde bis( 2-methoxyethyl)acetal, 2-thiobenzoylacetaldehyde bis(2-methoxy-ethyl)acetal, and 2-thioacetaldehyde bis(2-methoxyethyl)acetal, are useful as intermediates in the synthesis of substituted 1,3-oxathiolanes and substituted 1,3-dioxolanes.
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1: Ilbeigi K, Mabille D, Matheeussen A, Hendrickx R, Claes M, Van Reet N, Anthonissen R, Hulpia F, Lin C, Maes L, Regnault C, Whitfield P, Roy R, Ungogo MA, Sterckx YG, De Winter H, Mertens B, Bundschuh M, De Koning HP, Van Calenbergh S, Caljon G. Discovery and Development of an Advanced Lead for the Treatment of African Trypanosomiasis. ACS Infect Dis. 2025 Jan 10;11(1):131-143. doi: 10.1021/acsinfecdis.4c00472. Epub 2024 Dec 12.
381:114930. doi: 10.1016/j.expneurol.2024.114930. Epub 2024 Aug 21. 151(5):506-513. doi: 10.1017/S0031182024000362. Epub 2024 Mar 27.
4: Lian Y, Huang Z, Liu X, Deng Z, Gao D, Wang X. Discovery of Ten Anti-HIV Hit Compounds and Preliminary Pharmacological Mechanisms Studies. Curr HIV Res. 2024;22(2):82-90. doi: 10.2174/011570162X301289240320082840. 40(3):235-243. Chinese. 12(3):e0347923. doi: 10.1128/spectrum.03479-23. Epub 2024 Feb 1.

合成参考文献


摘要:Wicha, J., Science of Synthesis, (2009) 48, 181.
摘要:National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program., JAN1986
摘要:Journal of Antibiotics, Series A., 10(201), 1957
摘要:Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory., 2(6)(-), 1971
摘要:Cancer Research., 29(116), 1969 []
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