• 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

利用尼古拉斯反应通过在修饰的有机金属核苷中形成碳 - 碳键来延长5 - 炔基尿苷侧链。

Extension of the 5-alkynyluridine side chain via C-C-bond formation in modified organometallic nucleosides using the Nicholas reaction.

作者信息

Kaczmarek Renata, Korczyński Dariusz, Green James R, Dembinski Roman

机构信息

Department of Bioorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland.

Department of Chemistry and Biochemistry, University of Windsor, Windsor, Ontario, N9B 3P4, Canada.

出版信息

Beilstein J Org Chem. 2020 Jan 2;16:1-8. doi: 10.3762/bjoc.16.1. eCollection 2020.

DOI:10.3762/bjoc.16.1
PMID:31976010
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6964655/
Abstract

Dicobalt hexacarbonyl nucleoside complexes of propargyl ether or esters of 5-substituted uridines react with diverse C-nucleophiles. Synthetic outcomes confirmed that the Nicholas reaction can be carried out in a nucleoside presence, leading to a divergent synthesis of novel metallo-nucleosides enriched with alkene, arene, arylketo, and heterocyclic functions, in the deoxy and ribo series.

摘要

5-取代尿苷的炔丙基醚或酯的二钴六羰基核苷配合物可与多种碳亲核试剂发生反应。合成结果证实，尼古拉斯反应可在核苷存在下进行，从而在脱氧和核糖系列中实现对富含烯烃、芳烃、芳基酮和杂环官能团的新型金属核苷的发散性合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/46b6/6964655/71002b2a68ee/Beilstein_J_Org_Chem-16-01-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/46b6/6964655/68998c3699ff/Beilstein_J_Org_Chem-16-01-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/46b6/6964655/71002b2a68ee/Beilstein_J_Org_Chem-16-01-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/46b6/6964655/68998c3699ff/Beilstein_J_Org_Chem-16-01-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/46b6/6964655/71002b2a68ee/Beilstein_J_Org_Chem-16-01-g002.jpg

相似文献

1
Extension of the 5-alkynyluridine side chain via C-C-bond formation in modified organometallic nucleosides using the Nicholas reaction.利用尼古拉斯反应通过在修饰的有机金属核苷中形成碳 - 碳键来延长5 - 炔基尿苷侧链。
Beilstein J Org Chem. 2020 Jan 2;16:1-8. doi: 10.3762/bjoc.16.1. eCollection 2020.
2
Organometallic Nucleosides: Synthesis and Biological Evaluation of Substituted Dicobalt Hexacarbonyl 2'-Deoxy-5-oxopropynyluridines.有机金属核苷：取代的二钴六羰基-2'-脱氧-5-氧代丙炔基尿苷的合成与生物学评价
ChemistryOpen. 2018 Jan 18;7(3):237-247. doi: 10.1002/open.201700168. eCollection 2018 Mar.
3
Synthesis and Determination of Anticancer Activity of Dicobalt Hexacarbonyl 2'-Deoxy-5-alkynylfuropyrimidines.二钴六羰基-2'-脱氧-5-炔基呋喃嘧啶的合成及其抗癌活性测定
ACS Med Chem Lett. 2023 Jun 29;14(7):962-969. doi: 10.1021/acsmedchemlett.3c00152. eCollection 2023 Jul 13.
4
A substrate-based approach to skeletal diversity from dicobalt hexacarbonyl (C1)-alkynyl glycals by exploiting its combined Ferrier-Nicholas reactivity.一种基于底物的方法，通过利用二羰基钴（C1）-炔基糖烯的组合费里尔-尼古拉斯反应性来实现骨骼多样性。
Chemistry. 2014 Aug 11;20(33):10492-502. doi: 10.1002/chem.201402149. Epub 2014 Jul 10.
5
Metallo-nucleosides: synthesis and biological evaluation of hexacarbonyl dicobalt 5-alkynyl-2'-deoxyuridines.金属核苷：六羰基二钴5-炔基-2'-脱氧尿苷的合成与生物学评价
Org Biomol Chem. 2008 Jan 7;6(1):73-80. doi: 10.1039/b713371e. Epub 2007 Nov 26.
6
Gold(i)-catalyzed Nicholas reaction with aromatic molecules utilizing a bifunctional propargyl dicobalt hexacarbonyl complex.金（i）催化的与芳族分子的 Nicholas 反应，利用双官能团丙二炔二钴六羰基络合物。
Org Biomol Chem. 2019 Sep 25;17(37):8522-8526. doi: 10.1039/c9ob01348b.
7
Formation and reactivity of novel pyranosidic nicholas oxocarbenium ions: access to C-ketosides and branched-chain C-ketosides.新型吡喃糖苷型尼古拉斯氧鎓离子的形成与反应活性：通往C-酮糖苷和支链C-酮糖苷的途径。
Org Lett. 2006 Jul 20;8(15):3187-90. doi: 10.1021/ol060929+.
8
Formation and reactivity of new Nicholas-Ferrier pyranosidic cations: novel access to oxepanes via a 1,6-hydride shift/cyclization sequence.新型尼古拉斯-费里尔吡喃糖阳离子的形成和反应性：通过 1,6-氢化物转移/环化序列获得新型氧杂环丁烷。
Chem Commun (Camb). 2010 Sep 7;46(33):6159-61. doi: 10.1039/c0cc00586j. Epub 2010 Jul 26.
9
Catalytic Deprotection of Alkyne Dicobalt Hexacarbonyl Complexes using Near-Infrared Photocatalysis.使用近红外光催化对炔基二钴六羰基配合物进行催化脱保护
J Org Chem. 2024 Oct 18;89(20):15217-15224. doi: 10.1021/acs.joc.4c02009. Epub 2024 Oct 7.
10
Alkyne Ligation Handles: Propargylation of Hydroxyl, Sulfhydryl, Amino, and Carboxyl Groups via the Nicholas Reaction.炔烃连接手柄：通过 Nicholas 反应实现羟基、巯基、氨基和羧基的丙炔基化。
Org Lett. 2016 Sep 16;18(18):4566-9. doi: 10.1021/acs.orglett.6b02088. Epub 2016 Aug 29.

引用本文的文献

1
Synthesis and Determination of Anticancer Activity of Dicobalt Hexacarbonyl 2'-Deoxy-5-alkynylfuropyrimidines.二钴六羰基-2'-脱氧-5-炔基呋喃嘧啶的合成及其抗癌活性测定
ACS Med Chem Lett. 2023 Jun 29;14(7):962-969. doi: 10.1021/acsmedchemlett.3c00152. eCollection 2023 Jul 13.
2
Ferrocenoyl-adenines: substituent effects on regioselective acylation.二茂铁酰基腺嘌呤：取代基对区域选择性酰化的影响。
Beilstein J Org Chem. 2022 Sep 19;18:1270-1277. doi: 10.3762/bjoc.18.133. eCollection 2022.
3
Intramolecular Nicholas Reaction Enables the Stereoselective Synthesis of Strained Cyclooctynes.

本文引用的文献

1
Synthesis, toxicity and antitumor activity of cobalt carbonyl complexes targeting hepatocellular carcinoma.针对肝癌的钴羰基配合物的合成、毒性及抗肿瘤活性。
Bioorg Med Chem. 2019 Oct 15;27(20):115071. doi: 10.1016/j.bmc.2019.115071. Epub 2019 Aug 23.
2
Synthesis and Evaluation of Carbonic Anhydrase Inhibitors with Carbon Monoxide Releasing Properties for the Management of Rheumatoid Arthritis.具有一氧化碳释放性能的碳酸酐酶抑制剂的合成与评价及其在类风湿性关节炎治疗中的应用。
J Med Chem. 2019 Aug 8;62(15):7233-7249. doi: 10.1021/acs.jmedchem.9b00845. Epub 2019 Jul 23.
3
Introduction: Metals in Medicine.
分子内 Nicholas 反应实现了应变环辛炔的立体选择性合成。
Molecules. 2021 Mar 15;26(6):1629. doi: 10.3390/molecules26061629.
4
Extension of furopyrimidine nucleosides with 5-alkynyl substituent: Synthesis, high fluorescence, and antiviral effect in the absence of free ribose hydroxyl groups.将呋喃嘧啶核苷的 5-炔基取代物进行扩展：在没有游离核糖羟基的情况下的合成、高荧光和抗病毒效果。
Eur J Med Chem. 2021 Jan 1;209:112884. doi: 10.1016/j.ejmech.2020.112884. Epub 2020 Sep 28.
引言：医学中的金属
Chem Rev. 2019 Jan 23;119(2):727-729. doi: 10.1021/acs.chemrev.8b00685.
4
Stereoselective Synthesis of Highly Functionalized Arabinosyl Nucleosides through Application of an N-Nitro Protecting Group.通过应用N-硝基保护基团立体选择性合成高度官能化的阿拉伯糖基核苷。
J Org Chem. 2018 Oct 5;83(19):11944-11955. doi: 10.1021/acs.joc.8b01834. Epub 2018 Sep 6.
5
Design of "Click" Fluorescent Labeled 2'-deoxyuridines via C5-[4-(2-Propynyl(methyl)amino)]phenyl Acetylene as a Universal Linker: Synthesis, Photophysical Properties, and Interaction with BSA.通过 C5-[4-(2-丙炔基（甲基）氨基)]苯乙炔作为通用连接子设计“点击”荧光标记 2'-脱氧尿苷：合成、光物理性质以及与 BSA 的相互作用。
J Org Chem. 2018 Aug 3;83(15):7606-7621. doi: 10.1021/acs.joc.7b03097. Epub 2018 Jun 18.
6
Organometallic Nucleosides: Synthesis and Biological Evaluation of Substituted Dicobalt Hexacarbonyl 2'-Deoxy-5-oxopropynyluridines.有机金属核苷：取代的二钴六羰基-2'-脱氧-5-氧代丙炔基尿苷的合成与生物学评价
ChemistryOpen. 2018 Jan 18;7(3):237-247. doi: 10.1002/open.201700168. eCollection 2018 Mar.
7
Expanding the chemical diversity of TNA with tUTP derivatives that are substrates for a TNA polymerase.用作为TNA聚合酶底物的tUTP衍生物扩展TNA的化学多样性。
Chem Commun (Camb). 2018 Jan 31;54(10):1237-1240. doi: 10.1039/c7cc09130c.
8
Metal Complexes and Medicine: A Successful Combination.金属配合物与医学：成功的结合。
Chimia (Aarau). 2015 Aug 19;69(7):442-446. doi: 10.2533/chimia.2015.442.
9
Structural Insights into the Processing of Nucleobase-Modified Nucleotides by DNA Polymerases.DNA聚合酶对核碱基修饰核苷酸加工过程的结构见解
Acc Chem Res. 2016 Mar 15;49(3):418-27. doi: 10.1021/acs.accounts.5b00544. Epub 2016 Mar 5.
10
Advances in cobalt complexes as anticancer agents.钴配合物作为抗癌剂的研究进展。
Dalton Trans. 2015 Aug 21;44(31):13796-808. doi: 10.1039/c5dt02101d.