• 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

丙二腈活化的苯乙烯基喹喔啉-2(1)-酮的合成及其抗胆碱酯酶活性

Malononitrile-activated synthesis and anti-cholinesterase activity of styrylquinoxalin-2(1)-ones.

作者信息

Mahajan Sheena, Slathia Nancy, Nuthakki Vijay K, Bharate Sandip B, Kapoor Kamal K

机构信息

Department of Chemistry, University of Jammu Jammu-180006 India

Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine Canal Road Jammu-180001 India.

出版信息

RSC Adv. 2020 Apr 21;10(27):15966-15975. doi: 10.1039/d0ra02816a.

DOI:10.1039/d0ra02816a
PMID:35493659
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9052867/
Abstract

Herein, we report a base-free malononitrile activated condensation of 3-methylquinoxaline-2(1)-one (3MQ) 1 with aryl aldehydes 3a-3ad for synthesis of styrylquinoxalin-2(1)-ones (SQs) 4a-4ad with excellent yields. In this reaction, malononitrile activates the aldehyde Knoevenagel condensation towards reaction with 3MQ 1 and gets liberated during the course of reaction to yield the desired SQs 4a-4ad. The SQs were evaluated for cholinesterase inhibition and 4n was found to display a mixed type of inhibition of AChE, which was supported by molecular modelling studies. This study has led to the discovery of a new chemotype for cholinesterase inhibition which might be useful in finding a remedy for Alzheimer's disease.

摘要

在此，我们报道了一种无碱条件下丙二腈活化的3-甲基喹喔啉-2(1)-酮(3MQ) 1与芳醛3a - 3ad的缩合反应，用于合成产率优异的苯乙烯基喹喔啉-2(1)-酮(SQs) 4a - 4ad。在该反应中，丙二腈活化醛的Knoevenagel缩合反应，使其与3MQ 1发生反应，并在反应过程中释放出来，生成所需的SQs 4a - 4ad。对SQs进行了胆碱酯酶抑制活性评估，发现4n对乙酰胆碱酯酶(AChE)表现出混合型抑制作用，分子模拟研究支持了这一结果。该研究发现了一种新的胆碱酯酶抑制化学类型，这可能有助于找到治疗阿尔茨海默病的方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/f2b42f6bfb39/d0ra02816a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/14e6cd618052/d0ra02816a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/dba9fe0f6904/d0ra02816a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/92dfe219c3af/d0ra02816a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/be4fd8a7acb7/d0ra02816a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/50f035125a50/d0ra02816a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/f1b0c9cb2a86/d0ra02816a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/ad499b5bface/d0ra02816a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/f2b42f6bfb39/d0ra02816a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/14e6cd618052/d0ra02816a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/dba9fe0f6904/d0ra02816a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/92dfe219c3af/d0ra02816a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/be4fd8a7acb7/d0ra02816a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/50f035125a50/d0ra02816a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/f1b0c9cb2a86/d0ra02816a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/ad499b5bface/d0ra02816a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2301/9052867/f2b42f6bfb39/d0ra02816a-f4.jpg

相似文献

1
Malononitrile-activated synthesis and anti-cholinesterase activity of styrylquinoxalin-2(1)-ones.丙二腈活化的苯乙烯基喹喔啉-2(1)-酮的合成及其抗胆碱酯酶活性
RSC Adv. 2020 Apr 21;10(27):15966-15975. doi: 10.1039/d0ra02816a.
2
Superparamagnetic Poly(aniline-co-m-phenylenediamine)@FeO Nanocomposite as an Efficient Heterogeneous Catalyst for the Synthesis of 1-pyrazolo[1,2-]pyridazine-5,8-diones & 1-pyrazolo[1,2-]phthalazine-5, 10-diones Derivatives.超顺磁性聚（苯胺 - 间苯二胺）@FeO纳米复合材料作为合成1 - 吡唑并[1,2 - ]哒嗪 - 5,8 - 二酮和1 - 吡唑并[1,2 - ]酞嗪 - 5,10 - 二酮衍生物的高效多相催化剂
Curr Org Synth. 2022 Mar 3;19(2):246-266. doi: 10.2174/1570179418666211104143736.
3
A cascade synthesis, in vitro cholinesterases inhibitory activity and docking studies of novel Tacrine-pyranopyrazole derivatives.新型他克林-吡喃并吡唑衍生物的级联合成、体外胆碱酯酶抑制活性及对接研究
Bioorg Med Chem Lett. 2018 Aug 1;28(14):2481-2484. doi: 10.1016/j.bmcl.2018.05.063. Epub 2018 Jun 1.
4
Bromine-Promoted One-Pot Furo[]annulation and α-C(sp)-Thiomethylation Cascade of ()-3-Styrylquinoxalin-2(1)-ones with Dimethyl Sulfoxide.溴促进的（）-3-苯乙烯基喹喔啉-2（1）-酮与二甲基亚砜的一锅法呋喃并[ ]环化和α-C（sp）-硫甲基化串联反应
J Org Chem. 2022 Sep 16;87(18):12072-12086. doi: 10.1021/acs.joc.2c01158. Epub 2022 Sep 7.
5
Pot, atom and step economic (PASE) assembly of salicylaldehydes, malononitrile dimer and 4-hydroxypyridine-2(1H)-ones into medicinally relevant 5H-chromeno[2,3-b]pyridine scaffold.一锅原子经济性（PASE）组装法合成具有药用价值的 5H-色烯并[2,3-b]吡啶骨架的水杨醛、丙二腈二聚体和 4-羟基-2(1H)-吡啶酮。
Mol Divers. 2020 Aug;24(3):617-626. doi: 10.1007/s11030-019-09968-x. Epub 2019 Jun 8.
6
Impact of an aryl bulky group on a one-pot reaction of aldehyde with malononitrile and -substituted 2-cyanoacetamide.芳基大体积基团对醛与丙二腈及α-取代的2-氰基乙酰胺一锅法反应的影响
RSC Adv. 2019 Sep 13;9(49):28886-28893. doi: 10.1039/c9ra05975j. eCollection 2019 Sep 9.
7
A one-pot domino synthesis and discovery of highly functionalized dihydrobenzo[b]thiophenes as AChE inhibitors.一锅多米诺合成及发现高官能化二氢苯并[b]噻吩作为乙酰胆碱酯酶抑制剂。
Bioorg Med Chem Lett. 2013 Apr 1;23(7):2101-5. doi: 10.1016/j.bmcl.2013.01.122. Epub 2013 Feb 8.
8
Hydroxyapatite supported caesium carbonate as a new recyclable solid base catalyst for the Knoevenagel condensation in water.羟基磷灰石负载碳酸铯作为一种新型可回收的固体碱催化剂用于水相中的 Knoevenagel 缩合反应。
Beilstein J Org Chem. 2009 Nov 20;5:68. doi: 10.3762/bjoc.5.68.
9
Enzyme Promiscuity as a Remedy for the Common Problems with Knoevenagel Condensation.酶的多功能性可作为解决 Knoevenagel 缩合常见问题的方法。
Chemistry. 2019 Aug 1;25(43):10156-10164. doi: 10.1002/chem.201901491. Epub 2019 Jul 1.
10
Efficient three-component one-pot synthesis of fully substituted pyridin-2(1H)-ones via tandem Knoevenagel condensation-ring-opening of cyclopropane-intramolecular cyclization.通过串联Knoevenagel缩合-环丙烷开环-分子内环化高效一锅法合成全取代吡啶-2(1H)-酮
Chem Commun (Camb). 2009 Jun 28(24):3636-8. doi: 10.1039/b905742k. Epub 2009 May 13.

引用本文的文献

1
An Energetic and Topological Approach to Understanding the Interplay of Noncovalent Interactions in a Series of Crystalline Spiropyrrolizine Compounds.一种用于理解一系列结晶螺吡咯嗪化合物中非共价相互作用相互作用的能量和拓扑方法。
ACS Omega. 2024 Aug 15;9(34):36242-36258. doi: 10.1021/acsomega.4c02511. eCollection 2024 Aug 27.
2
Advances in organocatalyzed synthesis of organic compounds.有机催化合成有机化合物的进展。
RSC Adv. 2024 Jun 25;14(28):20365-20389. doi: 10.1039/d4ra03046j. eCollection 2024 Jun 18.
3
Vanillin: A Promising Biosourced Building Block for the Preparation of Various Heterocycles.

本文引用的文献

1
Current and emerging therapeutic targets of alzheimer's disease for the design of multi-target directed ligands.用于设计多靶点导向配体的阿尔茨海默病当前及新出现的治疗靶点
Medchemcomm. 2019 Oct 16;10(12):2052-2072. doi: 10.1039/c9md00337a. eCollection 2019 Dec 1.
2
Synthesis and biological evaluation of indoloquinoline alkaloid cryptolepine and its bromo-derivative as dual cholinesterase inhibitors.吲哚喹啉生物碱苦参碱及其溴代衍生物的合成与生物评价作为双胆碱酯酶抑制剂。
Bioorg Chem. 2019 Sep;90:103062. doi: 10.1016/j.bioorg.2019.103062. Epub 2019 Jun 12.
3
Identification of embelin, a 3-undecyl-1,4-benzoquinone from Embelia ribes as a multitargeted anti-Alzheimer agent.
香草醛：一种用于制备各种杂环化合物的有前景的生物源构建单元。
Front Chem. 2022 Jul 7;10:949355. doi: 10.3389/fchem.2022.949355. eCollection 2022.
鉴定出植酸，一种来自余甘子的 3-十一烷基-1,4-苯醌，作为一种多靶点抗阿尔茨海默病药物。
Drug Dev Res. 2019 Aug;80(5):655-665. doi: 10.1002/ddr.21544. Epub 2019 May 3.
4
Designing of acyl sulphonamide based quinoxalinones as multifunctional aldose reductase inhibitors.设计基于酰基磺酰胺的喹喔啉酮作为多功能醛糖还原酶抑制剂。
Bioorg Med Chem. 2019 Apr 15;27(8):1658-1669. doi: 10.1016/j.bmc.2019.03.015. Epub 2019 Mar 7.
5
Radical Ions of 3-Styryl-quinoxalin-2-one Derivatives Studied by Pulse Radiolysis in Organic Solvents.在有机溶剂中通过脉冲辐解研究3-苯乙烯基喹喔啉-2-酮衍生物的自由基离子
J Phys Chem B. 2018 Apr 12;122(14):4051-4066. doi: 10.1021/acs.jpcb.8b01004. Epub 2018 Mar 27.
6
Comparison of the Binding of Reversible Inhibitors to Human Butyrylcholinesterase and Acetylcholinesterase: A Crystallographic, Kinetic and Calorimetric Study.比较可逆抑制剂与人丁酰胆碱酯酶和乙酰胆碱酯酶的结合：晶体学、动力学和量热研究。
Molecules. 2017 Nov 29;22(12):2098. doi: 10.3390/molecules22122098.
7
Exploiting the Distal Reactivity of Indolyl Methylenemalononitriles: An Asymmetric Organocatalyzed [4+2] Cycloaddition with Enals Enables the Assembly of Elusive Dihydrocarbazoles.利用吲哚基亚甲基丙二腈的远端反应性：与烯醛的不对称有机催化[4+2]环加成反应实现了难以捉摸的二氢咔唑的组装。
Chemistry. 2016 Aug 26;22(36):12637-40. doi: 10.1002/chem.201602793. Epub 2016 Jul 28.
8
Design, synthesis, and biological evaluation of 3-vinyl-quinoxalin-2(1H)-one derivatives as novel antitumor inhibitors of FGFR1.3-乙烯基喹喔啉-2(1H)-酮衍生物作为新型FGFR1抗肿瘤抑制剂的设计、合成及生物学评价
Drug Des Devel Ther. 2016 May 3;10:1489-500. doi: 10.2147/DDDT.S88587. eCollection 2016.
9
Quinoxalinone (Part II). Discovery of (Z)-3-(2-(pyridin-4-yl)vinyl)quinoxalinone derivates as potent VEGFR-2 kinase inhibitors.喹喔啉酮（第二部分）。(Z)-3-(2-(吡啶-4-基)乙烯基)喹喔啉酮衍生物作为有效的血管内皮生长因子受体-2激酶抑制剂的发现。
Bioorg Med Chem. 2016 Apr 15;24(8):1840-52. doi: 10.1016/j.bmc.2016.03.008. Epub 2016 Mar 3.
10
Synthesis and in vivo diuretic activity of some new benzothiazole sulfonamides containing quinoxaline ring system.一些含喹喔啉环系的新型苯并噻唑磺酰胺的合成及其体内利尿活性
J Enzyme Inhib Med Chem. 2016 Dec;31(6):1682-9. doi: 10.3109/14756366.2015.1128425. Epub 2016 Jan 7.