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Synthesis and in vitro evaluation of new ethyl and methyl quinoxaline-7-carboxylate 1,4-di-N-oxide against Entamoeba histolytica.合成及新的乙基和甲基喹喔啉-7-羧酸 1,4-二-N-氧化物对溶组织内阿米巴的体外评价。
Bioorg Med Chem. 2013 Aug 1;21(15):4550-8. doi: 10.1016/j.bmc.2013.05.036. Epub 2013 Jun 1.
2
New salicylamide and sulfonamide derivatives of quinoxaline 1,4-di-N-oxide with antileishmanial and antimalarial activities.具有抗利什曼原虫和抗疟活性的喹喔啉 1,4-二 N-氧化物的新水杨酰胺和磺胺衍生物。
Bioorg Med Chem Lett. 2011 Aug 1;21(15):4498-502. doi: 10.1016/j.bmcl.2011.05.125. Epub 2011 Jun 12.
3
Synthesis and in vitro antitumor activity of substituted quinazoline and quinoxaline derivatives: search for anticancer agent.取代喹唑啉和喹喔啉衍生物的合成及体外抗肿瘤活性研究:寻找抗癌剂。
Eur J Med Chem. 2011 Jun;46(6):2327-46. doi: 10.1016/j.ejmech.2011.03.015. Epub 2011 Mar 15.
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Synthesis and biological activity of 7H-benzo[4,5]indolo[2,3-b]-quinoxaline derivatives.7H-苯并[4,5]吲哚并[2,3-b]喹喔啉衍生物的合成及生物活性。
Eur J Med Chem. 2011 Feb;46(2):794-8. doi: 10.1016/j.ejmech.2010.11.040. Epub 2010 Dec 1.
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New quinoxaline 1, 4-di-N-oxides: anticancer and hypoxia-selective therapeutic agents.新型喹喔啉 1,4-二 N-氧化物:抗癌和缺氧选择性治疗剂。
Eur J Med Chem. 2010 Jul;45(7):2733-8. doi: 10.1016/j.ejmech.2010.02.052. Epub 2010 Mar 1.
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Tirapazamine: a novel agent targeting hypoxic tumor cells.替拉扎明:一种靶向缺氧肿瘤细胞的新型药物。
Expert Opin Investig Drugs. 2009 Jan;18(1):77-87. doi: 10.1517/13543780802567250.
7
Synthesis and in vitro antitumor activity of new quinoxaline derivatives.新型喹喔啉衍生物的合成及其体外抗肿瘤活性
Eur J Med Chem. 2009 Apr;44(4):1579-91. doi: 10.1016/j.ejmech.2008.07.025. Epub 2008 Jul 26.
8
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Synthesis and biological evaluation of new 2-arylcarbonyl-3-trifluoromethylquinoxaline 1,4-di-N-oxide derivatives and their reduced analogues.新型2-芳基羰基-3-三氟甲基喹喔啉1,4-二氧化物衍生物及其还原类似物的合成与生物学评价
J Med Chem. 2007 Nov 1;50(22):5485-92. doi: 10.1021/jm0703993. Epub 2007 Oct 2.
10
The NCI60 human tumour cell line anticancer drug screen.美国国立癌症研究所60种人类肿瘤细胞系抗癌药物筛选
Nat Rev Cancer. 2006 Oct;6(10):813-23. doi: 10.1038/nrc1951.

基于NCI-60细胞株面板的对肿瘤细胞系具有细胞毒性活性的喹喔啉1,4-二氧化物酯类

Esters of Quinoxaline 1`4-Di--oxide with Cytotoxic Activity on Tumor Cell Lines Based on NCI-60 Panel.

作者信息

Rivera Gildardo, Ahmad Shah Syed Shoaib, Arrieta-Baez Daniel, Palos Isidro, Mongue Antonio, Sánchez-Torres Luvia Enid

机构信息

Centro de Biotecnología Genómica, Instituto Politécnico Nacional, Reynosa, México.

Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan.

出版信息

Iran J Pharm Res. 2017 Summer;16(3):953-965.

PMID:29201086
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5610751/
Abstract

Quinoxalines display diverse and interesting pharmacological activities as antibacterial, antiviral, antiparasitic and anticancer agents. Particularly, their 14-di--oxide derivatives have proved to be cytotoxic agents that are active under hypoxic conditions as that of solid tumours. A new series of quinoxaline 14-di--oxide substitutes at 7-position with esters group were synthetized and characterized by infrared (IR), proton nuclear magnetic resonance (H-NMR), spectroscopy, and elemental analysis. Seventeen derivatives (M1-M3, E1-E8, P1-P3 and DR1-DR3) were selected and evaluated for antitumor activities using the NCI-60 human tumor cell lines screen. Results showed that E7, P3 and E6 were the most active compounds against the cell lines tested. Substitutions at 7-position with esters group not necessarily affect the biological activity, but the nature of the esters group could exert an influence on the selectivity. Additionally, substitutions at 2-position influenced the cytotoxic activity of the compounds.

摘要

喹喔啉作为抗菌、抗病毒、抗寄生虫和抗癌药物具有多样且有趣的药理活性。特别是,它们的1,4 - 二氧化物衍生物已被证明是细胞毒性药物,在实体瘤的缺氧条件下具有活性。合成了一系列新的在7位带有酯基取代的喹喔啉1,4 - 二氧化物,并通过红外(IR)、质子核磁共振(H - NMR)光谱和元素分析进行了表征。选择了17种衍生物(M1 - M3、E1 - E8、P1 - P3和DR1 - DR3),并使用NCI - 60人肿瘤细胞系筛选评估其抗肿瘤活性。结果表明,E7、P3和E6是针对所测试细胞系最具活性的化合物。7位带有酯基的取代不一定会影响生物活性,但酯基的性质可能会对选择性产生影响。此外,2位的取代会影响化合物的细胞毒性活性。