• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

相似文献

1
5'-Halogeno-2',3'-cyclic sulphite isomers in the preparation of 5'-halogeno nucleosides. Synthesis of 5'-deoxyuridine and 5'-deoxy-5-fluorouridine.5'-卤代-2',3'-环亚硫酸酯异构体在5'-卤代核苷制备中的应用。5'-脱氧尿苷和5'-脱氧-5-氟尿苷的合成。
Nucleic Acids Res. 1978 Mar;5(3):1029-39. doi: 10.1093/nar/5.3.1029.
2
2',3'=Carbonates in the synthesis of uridine 5'-deoxy and 2',5'-dideoxy derivatives.2',3'-碳酸酯在尿苷5'-脱氧和2',5'-二脱氧衍生物合成中的应用
Nucleic Acids Res. 1976 Apr;3(4):1125-37. doi: 10.1093/nar/3.4.1125.
3
Antineoplastic activity of 3'-(chloroethyl)nitrosourea analogues of 2'-deoxyuridine and 2'-deoxy-5-fluorouridine.2'-脱氧尿苷和2'-脱氧-5-氟尿苷的3'-(氯乙基)亚硝基脲类似物的抗肿瘤活性。
J Med Chem. 1986 May;29(5):862-5. doi: 10.1021/jm00155a044.
4
Synthesis and properties of 5-fluorouracil oligonucleotides.
Nucleic Acids Symp Ser. 1995(34):27-8.
5
5'-[2-(2-Nitrophenyl)-2-methylpropionyl]-2'-deoxy-5-fluorouridine as a potential bioreductively activated prodrug of FUDR: synthesis, stability and reductive activation.5'-[2-(2-硝基苯基)-2-甲基丙酰基]-2'-脱氧-5-氟尿苷作为氟尿苷潜在的生物还原激活前药：合成、稳定性及还原激活
Bioorg Med Chem Lett. 2000 Apr 17;10(8):797-800. doi: 10.1016/s0960-894x(00)00108-6.
6
Synthesis of 4-formyl-4-imidazolin-2-one nucleosides, isomers of uridine and 2'-deoxyuridine.4-甲酰基-4-咪唑啉-2-酮核苷的合成，尿苷和2'-脱氧尿苷的异构体
Nucleosides Nucleotides Nucleic Acids. 2004;23(1-2):307-16. doi: 10.1081/ncn-120027837.
7
Identification and quantitation of 5-fluorouridine in rat urine after administration of 5-fluorouracil or 5-fluoro-2'-deoxyuridine.给予5-氟尿嘧啶或5-氟-2'-脱氧尿苷后大鼠尿液中5-氟尿苷的鉴定与定量分析。
Drug Metab Dispos. 1980 Sep-Oct;8(5):363-6.
8
Gas-liquid chromatographic analysis of fluoropyrimidine nucleosides and fluorouracil in plasma and urine.血浆和尿液中氟嘧啶核苷及氟尿嘧啶的气液色谱分析
Anal Biochem. 1985 Jun;147(2):478-86. doi: 10.1016/0003-2697(85)90301-x.
9
Glycosidic bond cleavage of 5-fluoro-2'-deoxyuridine and 5-fluorouridine by amino acyl-tRNA synthetases.氨基酰-tRNA合成酶对5-氟-2'-脱氧尿苷和5-氟尿苷的糖苷键裂解
Biochem Biophys Res Commun. 1990 Dec 14;173(2):731-5. doi: 10.1016/s0006-291x(05)80096-8.
10
Studies on 18F-labeled pyrimidines. II. Metabolic investigation of 18F-5-fluorouracil, 18F-5-fluoro-2'-deoxyuridine and 18F-5-fluorouridine in rats.18F标记嘧啶的研究。II. 大鼠体内18F-5-氟尿嘧啶、18F-5-氟-2'-脱氧尿苷和18F-5-氟尿苷的代谢研究。
Eur J Nucl Med. 1984;9(4):185-9. doi: 10.1007/BF00251469.

引用本文的文献

1
The effect of structural modifications of 5-fluorouracil derivatives on their transport and biodegradation by isolated rat jejunum.5-氟尿嘧啶衍生物的结构修饰对其经离体大鼠空肠转运及生物降解的影响。
Cancer Chemother Pharmacol. 1989;24(4):238-42. doi: 10.1007/BF00257625.

本文引用的文献

1
Direct halogenation of sugar moiety of nucleosides.核苷糖部分的直接卤化。
Tetrahedron Lett. 1971 Jan(2):87-90. doi: 10.1016/s0040-4039(01)96366-x.
2
On the reaction of Vilsmeier-Haack reagent with nucleoside: a convenient synthesis of 2,2'-cyclocytidine.
Tetrahedron Lett. 1970 Mar(11):867-70. doi: 10.1016/s0040-4039(01)97853-0.
3
Chemical synthesis and properties of analogs of adenosylcobalamin.
Biochemistry. 1974 Jun 18;13(13):2736-40. doi: 10.1021/bi00710a012.
4
2',3'=Carbonates in the synthesis of uridine 5'-deoxy and 2',5'-dideoxy derivatives.2',3'-碳酸酯在尿苷5'-脱氧和2',5'-二脱氧衍生物合成中的应用
Nucleic Acids Res. 1976 Apr;3(4):1125-37. doi: 10.1093/nar/3.4.1125.

5'-卤代-2',3'-环亚硫酸酯异构体在5'-卤代核苷制备中的应用。5'-脱氧尿苷和5'-脱氧-5-氟尿苷的合成。

5'-Halogeno-2',3'-cyclic sulphite isomers in the preparation of 5'-halogeno nucleosides. Synthesis of 5'-deoxyuridine and 5'-deoxy-5-fluorouridine.

作者信息

Hrebabecký H, Beránek J

出版信息

Nucleic Acids Res. 1978 Mar;5(3):1029-39. doi: 10.1093/nar/5.3.1029.

DOI:10.1093/nar/5.3.1029
PMID:148036
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC342042/
Abstract

When uridine (Ia) is reacted with thionyl chloride in hexamethylphosphoric triamide a mixture of isomeric 5'-chloro-2',3'-sulphites is formed, which can be separated to individual epimers IIa and IIIa, in 45% and 15% yields, respectively. Analogously, crystalline epimers IIb (37%) and IIIb (17%) can be obtained from 5-fluorouridine (Ib). Both isomers IIa, IIIa (or IIb, IIIb) afford a single 5'-chloro derivative IVa (or IVb, respectively) if treated with 0.1N sodium methoxide. From the mixture of sulphites IIa and IIIa (or IIb and IIIb) crystalline 5'-chlorouridine IVa is formed in 84.5% yield, calculated per starting uridine Ia (or crystalline 5'-chloro-5-fluorouridine IVb, 85.5% per starting 5-fluorouridine Ib, respectively). On reduction of 5'-chlorouridine IVa with tributyltin hydride 5'-deoxyuridine (Va) is formed in 79% yield. During the reduction of 5'-chloro-5-fluoro derivative IVb to 5'-deoxy-5-fluorouridine (Vb, 57%) a partial reductive elimination of 5-fluorine takes place under formation of 5'-deoxyuridine (Va, 9%).

摘要

当尿苷（Ia）与亚硫酰氯在六甲基磷酸三酰胺中反应时，会形成异构的5'-氯-2',3'-亚硫酸酯混合物，该混合物可分离为单个差向异构体IIa和IIIa，产率分别为45%和15%。类似地，从5-氟尿苷（Ib）可获得结晶差向异构体IIb（37%）和IIIb（17%）。如果用0.1N甲醇钠处理，两种异构体IIa、IIIa（或IIb、IIIb）都能得到单一的5'-氯衍生物IVa（或分别为IVb）。从亚硫酸酯IIa和IIIa（或IIb和IIIb）的混合物中，以起始尿苷Ia计算，结晶的5'-氯尿苷IVa的产率为84.5%（或以起始5-氟尿苷Ib计算，结晶的5'-氯-5-氟尿苷IVb的产率分别为85.5%）。用三丁基氢化锡还原5'-氯尿苷IVa时，5'-脱氧尿苷（Va）的产率为79%。在将5'-氯-5-氟衍生物IVb还原为5'-脱氧-5-氟尿苷（Vb，57%）的过程中，会发生5-氟的部分还原消除反应，生成5'-脱氧尿苷（Va，9%）。