• 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

合成具有非环 D-核糖基或 4-羟丁基链取代核糖的新型阿昔洛韦(AICA-核苷)类似物。

Synthesis of new acadesine (AICA-riboside) analogues having acyclic D-ribityl or 4-hydroxybutyl chains in place of the ribose.

机构信息

Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via D. Montesano 49, Napoli 80131, Italy.

出版信息

Molecules. 2013 Aug 6;18(8):9420-31. doi: 10.3390/molecules18089420.

DOI:10.3390/molecules18089420
PMID:23924994
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6269997/
Abstract

The antiviral activity of certain acyclic nucleosides drew our attention to the fact that the replacement of the furanose ring by an alkyl group bearing hydroxyl(s) could be a useful structural modification to modulate the biological properties of those nucleosides. Herein, we report on the synthesis of some novel acadesine analogues, where the ribose moiety is mimicked by a D-ribityl or by a hydroxybutyl chain.

摘要

某些无环核苷的抗病毒活性引起了我们的注意,即通过用带有羟基的烷基取代呋喃糖环,可以对这些核苷的生物学性质进行有用的结构修饰。在此,我们报告了一些新型阿昔洛韦类似物的合成,其中核糖部分由 D-核糖基或羟丁基链模拟。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e41f/6269997/e274115eec2f/molecules-18-09420-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e41f/6269997/0ff525c0b146/molecules-18-09420-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e41f/6269997/1512ac73ed09/molecules-18-09420-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e41f/6269997/e274115eec2f/molecules-18-09420-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e41f/6269997/0ff525c0b146/molecules-18-09420-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e41f/6269997/1512ac73ed09/molecules-18-09420-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e41f/6269997/e274115eec2f/molecules-18-09420-g003.jpg

相似文献

1
Synthesis of new acadesine (AICA-riboside) analogues having acyclic D-ribityl or 4-hydroxybutyl chains in place of the ribose.合成具有非环 D-核糖基或 4-羟丁基链取代核糖的新型阿昔洛韦(AICA-核苷)类似物。
Molecules. 2013 Aug 6;18(8):9420-31. doi: 10.3390/molecules18089420.
2
Acadesine (AICA riboside) inhibits platelet aggregation in human whole blood.
Adv Exp Med Biol. 1991;309A:55. doi: 10.1007/978-1-4899-2638-8_11.
3
Synthesis of 5-Aminoimidazole-4-Carboxamide Riboside (AICAR) and Its Derivatives Using Inosine as Starting Material.
Curr Protoc Nucleic Acid Chem. 2015 Dec 1;63:1.35.1-1.35.24. doi: 10.1002/0471142700.nc0135s63.
4
Regulation of adenosine concentrations by acadesine (AICA-riboside) in human B-lymphoblasts.
Adv Exp Med Biol. 1991;309A:275-8. doi: 10.1007/978-1-4899-2638-8_62.
5
Acadesine (AICA riboside) attenuates reperfusion injury and oxidant-induced damage of the heart.
Adv Exp Med Biol. 1991;309A:347. doi: 10.1007/978-1-4899-2638-8_78.
6
AICA riboside both activates AMP-activated protein kinase and competes with adenosine for the nucleoside transporter in the CA1 region of the rat hippocampus.2-氯腺苷既激活腺苷酸活化蛋白激酶,又在大鼠海马体CA1区与腺苷竞争核苷转运体。
J Neurochem. 2004 Mar;88(5):1272-82. doi: 10.1046/j.1471-4159.2003.02253.x.
7
Acyclic analogues of pyrazofurin: syntheses and antiviral evaluation.
Carbohydr Res. 1991 Sep 2;216:441-52. doi: 10.1016/0008-6215(92)84179-v.
8
AICA-riboside (acadesine), an activator of AMP-activated protein kinase with potential for application in hematologic malignancies.AICA-riboside(阿昔洛韦),一种 AMP 激活蛋白激酶的激活剂,具有在血液系统恶性肿瘤中的应用潜力。
Expert Opin Investig Drugs. 2010 Apr;19(4):571-8. doi: 10.1517/13543781003703694.
9
[Acyclic analogs of ribavirin. Synthesis and antiviral activity].[利巴韦林的无环类似物。合成与抗病毒活性]
Bioorg Khim. 1988 May;14(5):689-93.
10
Synthesis and biological activity of 5-thiobredinin and certain related 5-substituted imidazole-4-carboxamide ribonucleosides.5-硫代布雷迪宁及某些相关的5-取代咪唑-4-甲酰胺核糖核苷的合成与生物活性
J Med Chem. 1985 Sep;28(9):1198-203. doi: 10.1021/jm00147a013.

引用本文的文献

1
New Linear Precursors of cIDPR Derivatives as Stable Analogs of cADPR: A Potent Second Messenger with Ca-Modulating Activity Isolated from Sea Urchin Eggs.新型 cIDPR 衍生物线性前体作为 cADPR 的稳定类似物:从海胆卵中分离出的具有 Ca2+ 调节活性的强效第二信使。
Mar Drugs. 2019 Aug 17;17(8):476. doi: 10.3390/md17080476.
2
Synthesis and Biological Evaluation of a New Structural Simplified Analogue of cADPR, a Calcium-Mobilizing Secondary Messenger Firstly Isolated from Sea Urchin Eggs.新型结构简化 cADPR(最初从海胆卵中分离出的钙动员第二信使)类似物的合成与生物学评价。
Mar Drugs. 2018 Mar 10;16(3):89. doi: 10.3390/md16030089.
3

本文引用的文献

1
5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-Monophosphate (AICAR), a Highly Conserved Purine Intermediate with Multiple Effects.5-氨基咪唑-4-甲酰胺-1-β-D-呋喃核糖基5'-单磷酸(AICAR),一种具有多种作用的高度保守的嘌呤中间体。
Metabolites. 2012 Mar 23;2(2):292-302. doi: 10.3390/metabo2020292.
2
[Anti-HIV nucleoside drugs: retrospective view at future].[抗艾滋病毒核苷类药物:对未来的回顾性审视]
Mol Biol (Mosk). 2012 Nov-Dec;46(6):860-73.
3
A facile synthesis of 5'-fluoro-5'-deoxyacadesine (5'-F-AICAR): a novel non-phosphorylable AICAR analogue.
5-Amino-1-(2',3'--iso-propyl-idene-d-ribit-yl)-1-imidazole-4-carboxamide: a crystal structure with ' = 4.
5-氨基-1-(2',3'-异亚丙基-D-核醇基)-1-咪唑-4-甲酰胺:一种α = 4的晶体结构
Acta Crystallogr E Crystallogr Commun. 2017 Jan 13;73(Pt 2):183-187. doi: 10.1107/S2056989017000500. eCollection 2017 Feb 1.
4
Synthesis of cyclic N (1)-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells.环状N(1)-戊基肌苷磷酸的合成,一种对PC12细胞具有钙动员活性的新型结构简化的环ADP核糖类似物。
Beilstein J Org Chem. 2015 Dec 22;11:2689-2695. doi: 10.3762/bjoc.11.289. eCollection 2015.
5
Synthesis and pharmacological evaluation of modified adenosines joined to mono-functional platinum moieties.连接单功能铂部分的修饰腺苷的合成与药理评价。
Molecules. 2014 Jul 3;19(7):9339-53. doi: 10.3390/molecules19079339.
5'-氟-5'-脱氧阿糖胞苷(5'-F-AICAR)的简便合成:一种新型非磷酸化的 AICAR 类似物。
Molecules. 2012 Nov 2;17(11):13036-44. doi: 10.3390/molecules171113036.
4
Synthesis and biological evaluation of unprecedented ring-expanded nucleosides (RENs) containing the imidazo[4,5-d][1,2,6]oxadiazepine ring system.合成及含有咪唑并[4,5-d][1,2,6]噁二嗪环系的空前环扩核苷(RENs)的生物评价。
Chem Commun (Camb). 2012 Sep 25;48(74):9310-2. doi: 10.1039/c2cc33511e. Epub 2012 Aug 9.
5
Click fleximers: a modular approach to purine base-expanded ribonucleoside analogues.点击柔性分子:嘌呤碱基扩展核糖核苷类似物的模块化方法。
Org Biomol Chem. 2012 Aug 28;10(32):6521-5. doi: 10.1039/c2ob25678a. Epub 2012 Jul 3.
6
Diabetic cardiovascular disease--AMP-activated protein kinase (AMPK) as a therapeutic target.糖尿病心血管疾病——以AMP激活蛋白激酶(AMPK)作为治疗靶点
Cardiovasc Hematol Agents Med Chem. 2012 Sep;10(3):190-211. doi: 10.2174/187152512802651015.
7
Progress in the development of anti-hepatitis C virus nucleoside and nucleotide prodrugs.抗丙型肝炎病毒核苷和核苷酸前药的研究进展。
Future Med Chem. 2012 Apr;4(5):625-50. doi: 10.4155/fmc.12.10.
8
N(3)-protection of thymidine with Boc for an easy synthetic access to sugar-alkylated nucleoside analogs.用 Boc 对胸腺嘧啶进行 N(3)-保护,以方便合成糖基化核苷类似物。
Chem Biodivers. 2012 Mar;9(3):589-97. doi: 10.1002/cbdv.201100103.
9
AICAR prevents heat-induced sudden death in RyR1 mutant mice independent of AMPK activation.AICAR 可预防 RyR1 突变型小鼠的热诱导性心搏骤停,且不依赖于 AMPK 激活。
Nat Med. 2012 Jan 8;18(2):244-51. doi: 10.1038/nm.2598.
10
Solid-phase synthesis of a new diphosphate 5-aminoimidazole-4-carboxamide riboside (AICAR) derivative and studies toward cyclic AICAR diphosphate ribose.新型二磷酸 5-氨基咪唑-4-甲酰胺核苷(AICAR)衍生物的固相合成及环状 AICAR 二磷酸核糖的研究。
Molecules. 2011 Sep 21;16(9):8110-8. doi: 10.3390/molecules16098110.