• 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

来自无环结构单元的2(1)-吡嗪酮:合成方法及进一步衍生化

2(1)-Pyrazinones from acyclic building blocks: methods of synthesis and further derivatizations.

作者信息

Riesco-Llach Gerard, Planas Marta, Feliu Lidia, Joule John A

机构信息

LIPPSO, Department of Chemistry, Universitat de Girona Maria Aurèlia Capmany 69 Girona 17003 Spain

The School of Chemistry, The University of Manchester Manchester M13 9PL UK

出版信息

RSC Adv. 2023 Jan 4;13(2):1162-1184. doi: 10.1039/d2ra07227k. eCollection 2023 Jan 3.

DOI:10.1039/d2ra07227k
PMID:36686909
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9811941/
Abstract

Pyrazinones (2(1)-pyrazinones) are found as components of a range of natural substances and are involved in the preparation of a great number of bioactive molecules. Synthesis of such compounds, and analogues, requires knowledge of the heterocyclic properties of pyrazinones and, in particular, methods for their ring construction. This review deals with the strategies that have been developed for the synthesis of pyrazinones from acyclic precursors, especially α-amino acid-derived units, from the first examples in 1905 up to the most recent in 2021.

摘要

吡嗪酮(2(1)-吡嗪酮)是一系列天然物质的组成成分,并且参与了大量生物活性分子的制备。此类化合物及其类似物的合成需要了解吡嗪酮的杂环性质,尤其是其环构建方法。本综述涉及从1905年的首个实例到2021年的最新实例,由无环前体,特别是α-氨基酸衍生单元合成吡嗪酮所开发的策略。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/a3f576b6b6db/d2ra07227k-s23.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/9d35f394838a/d2ra07227k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/133796c8ba90/d2ra07227k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/da2ea6a6434e/d2ra07227k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/d486d7329e86/d2ra07227k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/ecd22203ae47/d2ra07227k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/6ab01d08e511/d2ra07227k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/c0e88d422fda/d2ra07227k-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/1026ff59307b/d2ra07227k-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/6b467cf683a3/d2ra07227k-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/a0155f55505d/d2ra07227k-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/6270211f4b3d/d2ra07227k-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/e22dac043f30/d2ra07227k-s10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/8a5df20bf199/d2ra07227k-s11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/73af651a14aa/d2ra07227k-s12.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/7cceee588490/d2ra07227k-s13.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/a3b3d7be7c82/d2ra07227k-s14.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/b2800d8fed64/d2ra07227k-s15.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/65add0cb6c0b/d2ra07227k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/e8fd704573ba/d2ra07227k-s18.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/7d3a9259a4c0/d2ra07227k-s19.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/f66bc8174fcd/d2ra07227k-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/883017b1116d/d2ra07227k-s20.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/3ad6b2a97bce/d2ra07227k-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/a3f576b6b6db/d2ra07227k-s23.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/9d35f394838a/d2ra07227k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/133796c8ba90/d2ra07227k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/da2ea6a6434e/d2ra07227k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/d486d7329e86/d2ra07227k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/ecd22203ae47/d2ra07227k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/6ab01d08e511/d2ra07227k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/c0e88d422fda/d2ra07227k-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/1026ff59307b/d2ra07227k-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/6b467cf683a3/d2ra07227k-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/a0155f55505d/d2ra07227k-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/6270211f4b3d/d2ra07227k-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/e22dac043f30/d2ra07227k-s10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/8a5df20bf199/d2ra07227k-s11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/73af651a14aa/d2ra07227k-s12.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/7cceee588490/d2ra07227k-s13.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/a3b3d7be7c82/d2ra07227k-s14.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/b2800d8fed64/d2ra07227k-s15.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/65add0cb6c0b/d2ra07227k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/e8fd704573ba/d2ra07227k-s18.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/7d3a9259a4c0/d2ra07227k-s19.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/f66bc8174fcd/d2ra07227k-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/883017b1116d/d2ra07227k-s20.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/3ad6b2a97bce/d2ra07227k-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8323/9811941/a3f576b6b6db/d2ra07227k-s23.jpg

相似文献

1
2(1)-Pyrazinones from acyclic building blocks: methods of synthesis and further derivatizations.来自无环结构单元的2(1)-吡嗪酮:合成方法及进一步衍生化
RSC Adv. 2023 Jan 4;13(2):1162-1184. doi: 10.1039/d2ra07227k. eCollection 2023 Jan 3.
2
Formation of Volatile Pyrazinones in Amadori Rearrangement Products and Maillard Reaction Systems and the Major Formation Pathways.挥发性吡嗪酮类化合物在阿马多里重排产物和美拉德反应体系中的形成及其主要形成途径。
J Agric Food Chem. 2024 May 8;72(18):10570-10578. doi: 10.1021/acs.jafc.3c09885. Epub 2024 Apr 23.
3
Formation of Volatile Pyrazinones in the Asparagine Maillard Reaction Systems and Novel Pyrazinone Formation Pathways in the Amidated-Alanine Maillard Reaction Systems.在天冬酰胺美拉德反应体系中挥发性吡嗪酮的形成和酰胺化丙氨酸美拉德反应体系中新型吡嗪酮形成途径。
J Agric Food Chem. 2024 May 15;72(19):11153-11163. doi: 10.1021/acs.jafc.4c02079. Epub 2024 May 2.
4
Potential antiviral agents. Part II. Synthesis and antiviral evaluation of pyrazinones substituted with acyclic chains.潜在的抗病毒药物。第二部分。无环链取代的吡嗪酮的合成与抗病毒评估。
Nucleosides Nucleotides. 1998 Aug;17(8):1489-504. doi: 10.1080/07328319808003482.
5
Bioactive 2(1H)-Pyrazinones and Diketopiperazine Alkaloids from a Tunicate-Derived Actinomycete Streptomyces sp.来自被囊动物源放线菌链霉菌属的生物活性2(1H)-吡嗪酮和二酮哌嗪生物碱
Molecules. 2016 Aug 24;21(9):1116. doi: 10.3390/molecules21091116.
6
Synthesis and antiviral evaluation of pyrazinones substituted with acyclic chains.无环链取代的吡嗪酮的合成与抗病毒评估
Nucleosides Nucleotides. 1998 May;17(5):875-93. doi: 10.1080/07328319808003460.
7
JBIR-56 and JBIR-57, 2(1H)-pyrazinones from a marine sponge-derived Streptomyces sp. SpD081030SC-03.海洋来源链霉菌 SpD081030SC-03 中分离得到的 2(1H)-吡嗪酮类化合物 JBIR-56 和 JBIR-57
J Nat Prod. 2011 Jul 22;74(7):1630-5. doi: 10.1021/np200386c. Epub 2011 Jul 5.
8
N-heterocyclic carbene catalyzed aroylation of 3,5-dichloro-2(1H)-pyrazinones.N-杂环卡宾催化 3,5-二氯-2(1H)-吡嗪酮的芳基化反应。
J Org Chem. 2011 Apr 15;76(8):2920-5. doi: 10.1021/jo200155n. Epub 2011 Mar 15.
9
A Novel Methodology for Synthesis of 1,5,6-Trisubstituted 2(1H)-Pyrazinones of Biological Interest.一种合成具有生物学意义的1,5,6-三取代2(1H)-吡嗪酮的新方法。
Chem Pharm Bull (Tokyo). 2017;65(4):365-372. doi: 10.1248/cpb.c16-00830.
10
A straightforward microwave method for rapid synthesis of N-1, C-6 functionalized 3,5-dichloro-2(1H)-pyrazinones.一种用于快速合成N-1、C-6官能化的3,5-二氯-2(1H)-吡嗪酮的直接微波方法。
Org Biomol Chem. 2009 Jul 7;7(13):2809-15. doi: 10.1039/b905501k. Epub 2009 May 27.

引用本文的文献

1
Identification and heterologous expression of an NRPS biosynthetic gene cluster responsible for the production of the pyrazinones Ichizinone A, B and C.负责吡嗪酮类化合物Ichizinone A、B和C生物合成的非核糖体肽合成酶(NRPS)生物合成基因簇的鉴定与异源表达。
Microb Cell Fact. 2025 Jun 7;24(1):131. doi: 10.1186/s12934-025-02753-6.
2
Pyrazinone Biosynthesis and Signaling-Myxo Style.吡嗪酮生物合成与信号传导——粘细菌模式
ACS Cent Sci. 2024 Mar 12;10(3):511-513. doi: 10.1021/acscentsci.4c00356. eCollection 2024 Mar 27.
3
Exploiting 3-Oxidopyraziniums toward Diazabicyclo[3.2.1]octanes and Their Conversion into Diazabicyclo[2.2.2]octanes and Tricyclic Lactone-Lactams.

本文引用的文献

1
Four-Component Synthesis of Polysubstituted Pyrazin-2(1)-ones through a Ugi/Staudinger/Aza-Wittig/Isomerization Sequence.通过 Ugi/Staudinger/Aza-Wittig/异构化序列合成多取代的吡嗪-2(1)-酮。
J Org Chem. 2021 Aug 6;86(15):10755-10761. doi: 10.1021/acs.joc.1c00735. Epub 2021 Jul 12.
2
Role of favipiravir in the treatment of COVID-19.法匹拉韦在治疗 COVID-19 中的作用。
Int J Infect Dis. 2021 Jan;102:501-508. doi: 10.1016/j.ijid.2020.10.069. Epub 2020 Oct 30.
3
The discovery and evaluation of 3-amino-2(1H)-pyrazinones as a novel series of selective p38α MAP kinase inhibitors.
利用3-氧化吡嗪鎓合成二氮杂双环[3.2.1]辛烷及其转化为二氮杂双环[2.2.2]辛烷和三环内酯-内酰胺。
J Org Chem. 2024 Mar 1;89(5):2904-2915. doi: 10.1021/acs.joc.3c02273. Epub 2024 Feb 8.
发现并评价 3-氨基-2(1H)-吡嗪酮类化合物作为新型的选择性 p38α MAP 激酶抑制剂。
Bioorg Med Chem Lett. 2020 Sep 15;30(18):127412. doi: 10.1016/j.bmcl.2020.127412. Epub 2020 Jul 15.
4
Synthesis and base-pairing properties of pyrazine nucleic acids.吡嗪核酸的合成及碱基配对特性
Nucleosides Nucleotides Nucleic Acids. 2020;39(6):866-891. doi: 10.1080/15257770.2020.1711525. Epub 2020 Mar 4.
5
Enhypyrazinones A and B, Pyrazinone Natural Products from a Marine-Derived Myxobacterium sp.恩杂米嗪 A 和 B,海洋来源粘细菌产生的吡嗪酮天然产物
Mar Drugs. 2019 Dec 12;17(12):698. doi: 10.3390/md17120698.
6
Discovery of 5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazin-2(1H)-one derivatives as new potent PB2 inhibitors.发现5-(5-氟-1H-吡咯并[2,3-b]吡啶-3-基)吡嗪-2(1H)-酮衍生物作为新型有效的PB2抑制剂
Bioorg Med Chem Lett. 2019 Jul 1;29(13):1609-1613. doi: 10.1016/j.bmcl.2019.04.042. Epub 2019 Apr 26.
7
Synthesis of the Nonribosomal Peptide Phevalin and Analogs.非核糖体肽苯丙缬氨酸及其类似物的合成。
J Org Chem. 2019 Mar 15;84(6):3647-3651. doi: 10.1021/acs.joc.8b03206. Epub 2019 Mar 1.
8
Phileucin - A Cyclic Dipeptide Similar to Phevalin (Aureusimine B) from Streptomyces coelicolor M1146.喜亮菌素-A:一种与来自天蓝色链霉菌M1146的苯缬氨酸(金黄亚胺B)类似的环二肽。
Nat Prod Commun. 2017 Jan;12(1):107-109.
9
A Novel Methodology for Synthesis of 1,5,6-Trisubstituted 2(1H)-Pyrazinones of Biological Interest.一种合成具有生物学意义的1,5,6-三取代2(1H)-吡嗪酮的新方法。
Chem Pharm Bull (Tokyo). 2017;65(4):365-372. doi: 10.1248/cpb.c16-00830.
10
Tubulin modulating antifungal and antiproliferative pyrazinone derivatives.微管蛋白调节性抗真菌和抗增殖吡嗪酮衍生物
Bioorg Med Chem. 2016 Feb 1;24(3):435-43. doi: 10.1016/j.bmc.2015.08.038. Epub 2015 Aug 28.