CAS: 59-14-3; 5-Bromo-1-((2R,4S,5R)-4-Hydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-yl)Pyrimidine-2,4(1H,3H)-Dione

该化合物是甲状腺的合成核核素比喻,其特点是在环的5处放置时替换溴原子,在分子生物学和生物化学中常用,作为DNA合成和细胞扩散研究的标志.BrdU在细胞循环的S阶段被吸收到新合成的DNA中,取代了甲状腺,使研究人员能够跟踪细胞分解和扩散.该化合物一般在水和有机溶剂中溶解,可以适应各种实验条件.BrdU可以使用免疫生物学化学和流动细胞测量中的特定抗体进行检测,便利对细胞过程的分析.此外,还研究了其对DNA修复机制和诱变过程的潜在影响.然而,在处理BrdU时,应谨慎小心谨慎,因为它在高浓度时可能具有细胞毒性.

结构式图片

相似化合物

6161-23-5 957-75-5 951-78-0

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CAS号951-78-0 2’-脱氧尿苷 | CAS号51-20-7 5-溴脲嘧啶 | CAS号6161-23-5 3',5'-二-O-乙酰基-5... | CAS号54-42-2 碘苷 | CAS号1463-10-1 5-甲基尿甙 | CAS号951-77-9 2’-脱氧胞苷 | CAS号50-89-5 beta-胸苷 | CAS号13030-62-1 3',5'-二-O-乙酰基-2... | CAS号146629-34-7 5-(TriMethylsta... | CAS号6161-23-5 3',5'-二-O-乙酰基-5... | CAS号50-89-5 beta-胸苷 | CAS号951-78-0 2’-脱氧尿苷 | CAS号154925-95-8 3',5'-双-O-(叔丁基二... | CAS号40733-26-4 3',5'-BIS-O-(叔丁...

合成工艺路线路线简述

  • 合成目标产物 Broxuridine 主要起始原料 5-Bromouracil And Thymidine
  • (文献来源)合成步骤主要原料 5-Bromouracil 和 Thymidine
[(2R,3S,5R)-5-(5-Bromo-2,4-Dioxopyrimidin-1-yl)-3-(4-Chlorobenzoyl)Oxyoxolan-2-Yl]Methyl 4-Chlorobenzoate置于氨体系中,用 甲醇 作为反应溶剂,化学反应 16.0H,反应生成 溴脲苷
参考文献:5-取代的2'-脱氧尿苷异头体的立体选择性合成
标题:5-取代的2'-脱氧尿苷异头体的立体选择性合成
摘要:研究了5-取代的2,4-双(三甲基甲硅烷氧基)嘧啶与3,5-双(Op-氯苯甲酰基)-2-脱氧-α-D-呋喃核糖基氯的取代反应.在对硝基苯酚的存在下,β端基异构体立体选择性地形成,而有机碱的加入导致α端基异构体的立体选择性形成.反应的立体选择性取决于二甲硅烷基嘧啶的 5 位取代基,添加剂和每种试剂的浓度.5-取代的2'-脱氧-尿苷的α和β异头通过5-取代3',5'-二-O-(对-氯苯甲酰基)-2'-脱氧尿苷的α和β异头脱酰化合成.
DOI:10.1246/bcsj.60.2073

海关参考信息

专利信息


专利号:US-2004014168-A1
优先权日:1998-06-11
标题:Reagents and methods for library synthesis and screening
发明人:SCHREIBER STUART L; BLACKWELL HELEN E; PEREZ FERNANDEZ LUCY; TALLARICO JOHN A
权利人:HUGHES HOWARD MED INST
摘要:The invention provides novel solid supports for the synthesis of compound libraries. The solid supports have the physical capacity to deliver at least 50 nmol of compound and are functionalized with a silicon-containing linker. In one embodiment of the invention the solid support comprises a bead having a diameter of between approximately 400 and 600 μm functionalized with a silicon-containing linker. According to certain embodiments of the invention the bead is a polystyrene bead. According to certain embodiments of the invention the linker is a diisopropylalkyl-substituted silyl ether. The invention further provides grafted polymeric supports such as lanterns functionalized with a silicon-containing linker. n The invention provides methods for screening in which compounds are synthesized on solid supports in a quantity so that a single solid support such as a bead provides a stock solution sufficient to perform hundreds or thousands of biological or chemical assays. The methods include decoding the sequence of chemical reactions used to synthesize the compound by identifying tags incorporated into the compound during synthesis.

专利号:EP-0799313-A2
优先权日:1994-12-13
标 题 :Method and reagent for treatment of arthritic conditions, induction of graft tolerance and reversal of immune responses
发明人:BEIGELMAN LEONID; STINCHCOMB DANIEL T; JARVIS THALE; DRAPER KENNETH; PAVCO PAMELA; MCSWIGGEN JAMES; GUSTOFSON JOHN; USMAN NASSIM; WINCOTT FRANCINE; MATULIC-ADAMIC JASENKA; KARPEISKY ALEXANDER; THOMPSON JAMES D; MODAK ANIL; BURGIN ALEX
权利人:RIBOZYME PHARM INC
摘要:An enzymatic nucleic acid molecule which cleaves RNA associated with development or maintenance of an arthritic condition, induction of graft tolerance or reversal of an immune response. In particular, the ribozyme sequences are directed to an mRNA encoding B7-1, B7-2, B7-3, CD40 and/or stromelysin. Also provided are ribozymes where the uracil in positions 4 and/or 7 are substituted, as well as methods for the synthesis of 2'-alkylnucleotides, 2'-O-alkylthioalkyl, or 2'-alkylthioalkylnucleotides. The application further describes a method for diprotection of RNA with aqueous ethylamine, a method for synthesis of a basic ribonucleoside mimetics, and transcription units comprising an RNA polymerase II promoter, a U6 small nuclear promoter, or an adenovirus VA1 promoter system.

专利号:US-5468853-A
优先权日:1993-12-30
标题 :Synthesis of 5-radiohalo-2'-deoxyuridine
发明人:BARANOWSKA-KORTYLEWICZ JANINA
权利人:UNIV NEBRASKA
摘要:Method of synthesizing 5-radio-halogenated-2'-deoxyuridine from 5-trimethylstannyl-2'-deoxyuridine is described. The method consists of the steps of mixing 5-trimethylstannyl-2'-deoxyuridine with an aqueous solution consisting of a radiohalide and NaOH to form a first mixture, adding H 2 O 2 /CH 3 COOH to the first mixture to form a second mixture, sonicating the second mixture, evaporating the solvent from the second mixture to form a residue, reconstituting the residue, filtering the residue; and then purifying the filtered residue such that at least one of a radiohalogenated nucleoside and nucleotide is obtained. A kit consisting of the components required for the above synthesis is also described.

专利号:US-9605261-B2
优先权日:2008-09-06
标 题:RNA synthesis—phosphoramidites for synthetic RNA in the reverse direction, and application in convenient introduction of ligands, chromophores and modifications of synthetic RNA at the 3′-end
发明人:SRIVASTAVA SURESH C; PANDEY DIVYA; BAJPAI SATYA P; SRIVASTAVA NAVEEN P
权利人:CHEMGENES CORP
摘要:The present invention relates to novel phosphoramidites, A-n-bz, C-n-bz, C-n-ac, G-n-ac and U are produced with an HPLC purity of greater than 98% and 31 P NMR purity greater than 99%. A novel process of reverse 5′→3′ directed synthesis of RNA oligomers has been developed and disclosed. Using that method demonstrated high quality RNA synthesis with coupling efficiency approaching 99%.

专利号:WO-2004087679-A1
优先权日:2003-04-01
标 题 :2, 4, 6-trisubstituted pyrimidine derivatives useful for the treatment of neoplastic and autoimmune diseases
发明人:OBRECHT DANIEL; ERMERT PHILIPP; LUTHER ANATOL; EBERLE MARTIN; BACHMANN FELIX
权利人:APONETICS AG; OBRECHT DANIEL; ERMERT PHILIPP; LUTHER ANATOL; EBERLE MARTIN; BACHMANN FELIX
摘要:The invention relates to substituted pyrimidines of formula (I) wherein V represents a bond or CR6R7, W represents a bond, NR8 or oxygen, X represents sulfur, or nitrogen substituted by hydrogen or R5, Y represents -CH2-, -CH2CH2-, -CO- or -CS-, R1 represents unsubstituted or substituted aryl or heteroaryl, and the substituents R2, R3, R4, R5, R6, R7 and R8 have the meanings given in the specification. These compounds are selectively inducing apoptosis in cancer cells and can be used for the treatment of neoplastic and autoimmune diseases. The invention relates also to methods of synthesis of such compounds, to their use as medicaments, to pharmaceutical compositions containing same, and to methods of treatment of neoplastic and autoimmune diseases using such compounds of formula (I) or of pharmaceutical compositions containing same.

专利号:US-7510852-B2
优先权日:2002-10-18
标题:Biosynthetic genes and host cells for the synthesis of polyketide antibiotics and method of use
发明人:ROYER MONIQUE; GABRIEL DEAN W; FRUTOS ROGER; ROTT PHILIPPE
权利人:CIRAD; UNIV FLORIDA
摘要:Three gene clusters that together encode albicidin biosynthesis, the complete gene DNA sequences, and the deduced protein sequences for the enzymes and methods for using the DNA sequences are disclosed and discussed as well as methods for plant protection and creating new antibiotics. The novel Albicidin family of antibiotics is disclosed and their structure deduced.
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1: Trussart C, Pirlot C, Di Valentin E, Piette J, Habraken Y. Melanoma antigen-D2 controls cell cycle progression and modulates the DNA damage response. Biochem Pharmacol. 2018 Jan 22. pii: S0006-2952(18)30035-2. doi: 10.1016/j.bcp.2018.01.035. [Epub ahead of print] doi: 10.3340/jkns.2017.0203.003. Epub 2017 Dec 29.
5: Tsuji M, Tanaka T, Nagashima R, Sagisaka Y, Tousen Y, Nishide Y, Ishimi Y, Ishimi Y. Effect of daidzein and equol on DNA replication in MCF-7 cells. J Biochem. 2018 Jan 15. doi: 10.1093/jb/mvy006. [Epub ahead of print] Chinese. doi: 10.18632/oncotarget.18195. eCollection 2017 Nov 24.
10: Zhou WJ, Yang HL, Chang KK, Meng Y, Wang MY, Yuan MM, Li MQ, Xie F. Human thymic stromal lymphopoietin promotes the proliferation and invasion of cervical cancer cells by downregulating microRNA-132 expression. Oncol Lett. 2017 Dec;14(6):7910-7916. doi: 10.3892/ol.2017.7260. Epub 2017 Oct 23.

合成参考文献


参考文献:10.1371/journal.pone.0022116
摘要:Hwang S, Kwak SH, Bhak J, Kang HS, Lee YR, Koo BK, Park KS, Lee HK, Cho YM. Gene Expression Pattern in Transmitochondrial Cytoplasmic Hybrid Cells Harboring Type 2 Diabetes-Associated Mitochondrial DNA Haplogroups. PLoS ONE. 2011 Jul 13;6(7):e22116. doi: 10.1371/journal.pone.0022116.
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