• 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

具有抗肿瘤和杀锥虫活性的醌亚胺和含硫化合物的合成:氧化还原及生物学意义

Synthesis of quinone imine and sulphur-containing compounds with antitumor and trypanocidal activities: redox and biological implications.

作者信息

Almeida Renata G, Valença Wagner O, Rosa Luísa G, de Simone Carlos A, de Castro Solange L, Barbosa Juliana M C, Pinheiro Daniel P, Paier Carlos R K, de Carvalho Guilherme G C, Pessoa Claudia, Goulart Marilia O F, Kharma Ammar, da Silva Júnior Eufrânio N

机构信息

Institute of Exact Sciences , Department of Chemistry , Federal University of Minas Gerais , Belo Horizonte , 31270-901 , MG , Brazil . Email:

Center for the Development of Chemical Technologies , State University of Mato Grosso do Sul , Naviraí , 79950-000 , MS , Brazil.

出版信息

RSC Med Chem. 2020 Jul 13;11(10):1145-1160. doi: 10.1039/d0md00072h. eCollection 2020 Oct 1.

DOI:10.1039/d0md00072h
PMID:33479619
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7651858/
Abstract

-Quinones represent a special class of redox active compounds associated with a spectrum of pronounced biological activities, including selective cytotoxicity and antimicrobial actions. The modification of the quinone ring by simple nitrogen and sulphur substitutions leads to several new classes of compounds with their own, distinct redox behaviour and equally distinct activities against cancer cell lines and . Some of the compounds investigated show activity against at concentrations of 24.3 and 65.6 μM with a selectivity index of around 1. These results demonstrate that simple chemical modifications on the -quinone ring system, in particular, by heteroatoms such as nitrogen and sulphur, transform these simple redox molecules into powerful cytotoxic agents with considerable "potential", not only in synthesis and electrochemistry, but also, in a broader sense, in health sciences.

摘要

醌类是一类特殊的氧化还原活性化合物,具有一系列显著的生物活性,包括选择性细胞毒性和抗菌作用。通过简单的氮和硫取代对醌环进行修饰,可产生几类新的化合物,它们具有各自独特的氧化还原行为,以及对癌细胞系同样独特的活性。一些研究的化合物在浓度为24.3和65.6 μM时对[具体对象未提及]显示出活性,选择性指数约为1。这些结果表明,特别是通过氮和硫等杂原子对醌环系统进行简单的化学修饰,可将这些简单的氧化还原分子转化为具有相当“潜力”的强大细胞毒性剂,不仅在合成和电化学方面,而且从更广泛的意义上讲,在健康科学领域也是如此。

相似文献

1
Synthesis of quinone imine and sulphur-containing compounds with antitumor and trypanocidal activities: redox and biological implications.具有抗肿瘤和杀锥虫活性的醌亚胺和含硫化合物的合成:氧化还原及生物学意义
RSC Med Chem. 2020 Jul 13;11(10):1145-1160. doi: 10.1039/d0md00072h. eCollection 2020 Oct 1.
2
Mode of action of p-quinone derivatives with trypanocidal activity studied by experimental and in silico models.通过实验模型和计算机模拟模型研究具有杀锥虫活性的对苯醌衍生物的作用模式。
Eur J Med Chem. 2023 Jan 15;246:114926. doi: 10.1016/j.ejmech.2022.114926. Epub 2022 Nov 17.
3
It takes two to tango: synthesis of cytotoxic quinones containing two redox active centers with potential antitumor activity.一个巴掌拍不响:具有潜在抗肿瘤活性的含两个氧化还原活性中心的细胞毒性醌类化合物的合成。
RSC Med Chem. 2021 Aug 12;12(10):1709-1721. doi: 10.1039/d1md00168j. eCollection 2021 Oct 20.
4
Rhodium-catalyzed C-H bond activation for the synthesis of quinonoid compounds: Significant Anti-Trypanosoma cruzi activities and electrochemical studies of functionalized quinones.用于合成醌类化合物的铑催化C-H键活化:功能化醌类化合物的显著抗克氏锥虫活性及电化学研究
Eur J Med Chem. 2017 Aug 18;136:406-419. doi: 10.1016/j.ejmech.2017.05.011. Epub 2017 May 4.
5
It Takes Two to Tango, Part II: Synthesis of A-Ring Functionalised Quinones Containing Two Redox-Active Centres with Antitumour Activities.探戈双人舞,第二部分:含两个具有抗肿瘤活性的氧化还原活性中心的 A-环功能化醌的合成。
Molecules. 2023 Feb 27;28(5):2222. doi: 10.3390/molecules28052222.
6
[Growth and DNA synthesis inhibition and superoxide anion formation by iminoquinones in Trypanosoma cruzi].[亚胺醌对克氏锥虫的生长、DNA合成抑制及超氧阴离子形成的影响]
Rev Argent Microbiol. 1988 Oct-Dec;20(4):183-93.
7
2-Phenylaminonaphthoquinones and related compounds: synthesis, trypanocidal and cytotoxic activities.2-苯基氨基萘醌及其相关化合物:合成、杀锥虫活性和细胞毒性
Bioorg Med Chem. 2014 Sep 1;22(17):4609-20. doi: 10.1016/j.bmc.2014.07.030. Epub 2014 Jul 27.
8
Synthesis of New Thiosemicarbazones and Semicarbazones Containing the 1,2,3-1H-triazole-isatin Scaffold: Trypanocidal, Cytotoxicity, Electrochemical Assays, and Molecular Docking.含1,2,3-1H-三唑-异吲哚酮骨架的新型硫代氨基脲和氨基脲的合成:抗锥虫活性、细胞毒性、电化学分析及分子对接
Med Chem. 2019;15(3):240-256. doi: 10.2174/1573406414666180912120502.
9
New aryloxy-quinone derivatives with promising activity on Trypanosoma cruzi.具有潜在活性的新型芳氧基-醌衍生物对克氏锥虫。
Arch Pharm (Weinheim). 2020 Jan;353(1):e1900213. doi: 10.1002/ardp.201900213. Epub 2019 Nov 11.
10
Design, synthesis, and evaluation of proliferation inhibitory activity of novel L-shaped ortho-quinone analogs as anticancer agents.新型L型邻醌类似物作为抗癌剂的设计、合成及增殖抑制活性评估
Bioorg Chem. 2021 Dec;117:105383. doi: 10.1016/j.bioorg.2021.105383. Epub 2021 Sep 22.

引用本文的文献

1
Studies of the Functionalized α-Hydroxy--Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen Bond.通过分子内氢键稳定的官能化α-羟基-醌亚胺衍生物的研究
Molecules. 2024 Apr 3;29(7):1613. doi: 10.3390/molecules29071613.
2
Anti-leishmanial activity of Herb. and predictions of isoeleutherin and its analogues.草药的抗利什曼原虫活性以及异刺五加素及其类似物的预测。
Front Chem. 2024 Mar 6;12:1341172. doi: 10.3389/fchem.2024.1341172. eCollection 2024.
3
Diversity-Orientated Synthesis and Biological Properties of Compounds Based on the -Phenylquinoneimine Scaffold.基于 - 苯醌亚胺骨架的化合物的多样性导向合成及生物性质研究。
Molecules. 2024 Jan 3;29(1):249. doi: 10.3390/molecules29010249.
4
Exploring the Antimicrobial and Antitumoral Activities of Naphthoquinone-Grafted Chitosans.探索萘醌接枝壳聚糖的抗菌和抗肿瘤活性。
Polymers (Basel). 2023 Mar 14;15(6):1430. doi: 10.3390/polym15061430.
5
Novel one-pot synthesis of a library of 2-aryloxy-1,4-naphthoquinone derivatives. Determination of antifungal and antibacterial activity.新型一锅法合成2-芳氧基-1,4-萘醌衍生物库。抗真菌和抗菌活性的测定。
RSC Adv. 2022 Jun 23;12(29):18507-18523. doi: 10.1039/d2ra01814d. eCollection 2022 Jun 22.
6
Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis.可见光促进的有氧钌催化仲胺和叔胺的室温脱烷基酰亚胺化反应。
RSC Adv. 2021 May 25;11(31):18966-18973. doi: 10.1039/d0ra10517a. eCollection 2021 May 24.
7
1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis.1,2-萘醌-4-磺酸盐在有机合成中的应用。
Beilstein J Org Chem. 2022 Jan 5;18:53-69. doi: 10.3762/bjoc.18.5. eCollection 2022.

本文引用的文献

1
Synthesis of quinones with highlighted biological applications: A critical update on the strategies towards bioactive compounds with emphasis on lapachones.具有突出生物应用的醌类化合物的合成:具有生物活性化合物策略的重要更新,重点是拉帕醌。
Eur J Med Chem. 2019 Oct 1;179:863-915. doi: 10.1016/j.ejmech.2019.06.056. Epub 2019 Jun 25.
2
Ruthenium-catalyzed C-H oxygenation of quinones by weak O-coordination for potent trypanocidal agents.钌催化的醌的 C-H 氧代反应通过弱 O-配位作用用于有效的杀锥虫剂。
Chem Commun (Camb). 2018 Nov 13;54(91):12840-12843. doi: 10.1039/c8cc07572g.
3
Combination of Aryl Diselenides/Hydrogen Peroxide and Carbon-Nanotube/Rhodium Nanohybrids for Naphthol Oxidation: An Efficient Route towards Trypanocidal Quinones.芳基二硒化物/过氧化氢和碳纳米管/铑纳米杂化物在萘酚氧化中的组合:一种针对杀锥虫醌类药物的有效途径。
Chemistry. 2018 Oct 12;24(57):15227-15235. doi: 10.1002/chem.201802773. Epub 2018 Sep 6.
4
Direct sequential C-H iodination/organoyl-thiolation for the benzenoid A-ring modification of quinonoid deactivated systems: a new protocol for potent trypanocidal quinones.直接顺序 C-H 碘代/芳基巯基化反应用于醌型失活体系的苯环修饰:一种新型的潜在杀锥虫醌类化合物的方法。
Org Biomol Chem. 2018 Mar 7;16(10):1686-1691. doi: 10.1039/c8ob00196k.
5
Synthesis of Selenium-Quinone Hybrid Compounds with Potential Antitumor Activity via Rh-Catalyzed C-H Bond Activation and Click Reactions.通过 Rh 催化的 C-H 键活化和点击反应合成具有潜在抗肿瘤活性的硒-醌杂化化合物。
Molecules. 2017 Dec 30;23(1):83. doi: 10.3390/molecules23010083.
6
Discovery of naphtho[1,2-d]oxazole derivatives as potential anti-HCV agents through inducing heme oxygenase-1 expression.通过诱导血红素加氧酶-1 的表达发现萘并[1,2-d]恶唑衍生物作为潜在的抗 HCV 药物。
Eur J Med Chem. 2018 Jan 1;143:970-982. doi: 10.1016/j.ejmech.2017.12.006. Epub 2017 Dec 5.
7
Naphthoquinones: A continuing source for discovery of therapeutic antineoplastic agents.萘醌类化合物:发现治疗抗肿瘤药物的持续来源。
Chem Biol Drug Des. 2018 Mar;91(3):681-690. doi: 10.1111/cbdd.13141. Epub 2017 Nov 28.
8
Lapachol and lapachone analogs: a journey of two decades of patent research(1997-2016).拉帕醇和拉帕酮类似物:二十年来专利研究的历程(1997-2016)。
Expert Opin Ther Pat. 2017 Oct;27(10):1111-1121. doi: 10.1080/13543776.2017.1339792. Epub 2017 Jun 14.
9
Chagas disease in Europe: A review for the internist in the globalized world.欧洲的恰加斯病:全球化世界中内科医生的综述。
Eur J Intern Med. 2017 Sep;43:6-15. doi: 10.1016/j.ejim.2017.05.001. Epub 2017 May 11.
10
Cost-effectiveness of Chagas disease screening in Latin American migrants at primary health-care centres in Europe: a Markov model analysis.欧洲初级保健中心的拉丁美洲移民中进行恰加斯病筛查的成本效益:马尔可夫模型分析。
Lancet Glob Health. 2017 Apr;5(4):e439-e447. doi: 10.1016/S2214-109X(17)30073-6. Epub 2017 Feb 28.