• 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

含2,4 - 二羟基苯基取代基的新型唑并噻嗪酮和氮杂噻嗪酮作为抗癌剂的合成、表征及药理评价

Synthesis, characterization, and pharmacological evaluation of novel azolo- and azinothiazinones containing 2,4-dihydroxyphenyl substituent as anticancer agents.

作者信息

Matysiak Joanna, Juszczak Małgorzata, Karpińska Monika M, Langner Ewa, Walczak Katarzyna, Lemieszek Marta, Skrzypek Alicja, Rzeski Wojciech, Niewiadomy Andrzej

机构信息

Department of Chemistry, University of Life Sciences in Lublin, Akademicka 15, 20-950 Lublin, Poland.

Department of Medical Biology, Institute of Rural Health in Lublin, Jaczewskiego 2, 20-090 Lublin, Poland.

出版信息

Monatsh Chem. 2015;146(8):1315-1327. doi: 10.1007/s00706-015-1453-4. Epub 2015 Apr 2.

DOI:10.1007/s00706-015-1453-4
PMID:26190864
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4498246/
Abstract

ABSTRACT

We reported the synthesis and characterization of a series of azolo- and azino[1,3]thiazinones containing the 2,4-dihydroxyphenyl substituent. The compounds were prepared by a new one-step reaction of aryl-modified sulfinylbis[(2,4-dihydroxyphenyl)methanethione]s and the corresponding aminoazolo(azino)carboxamides. Their chemical structures were confirmed by IR, NMR: H, C, HSQC, and EI-MS spectral data. The compounds inhibited proliferation and viability of lung cancer A549, colon cancer HT-29, and glioma C6 cells in a structure- and concentration-dependent manner. The activity of some analogues was below 10 μmol dm (IC). Glioma C6 cells were the most sensitive to tested compounds. Generally, the derivatives were not toxic for the skin fibroblast HSF culture. Moreover, some of them exerted a protective effect on the treated normal cells. Evaluation of compound properties in silico showed that they possess significant drug-like characteristics and most of them display a low toxicity.

摘要

摘要

我们报道了一系列含有2,4 - 二羟基苯基取代基的氮杂环并[1,3]噻嗪酮和氮杂环并嗪[1,3]噻嗪酮的合成与表征。这些化合物是通过芳基修饰的亚磺酰基双[(2,4 - 二羟基苯基)甲硫酮]与相应的氨基氮杂环(氮杂环并嗪)甲酰胺的新型一步反应制备的。通过红外光谱(IR)、核磁共振氢谱(H NMR)、碳谱(13C NMR)、异核单量子相干谱(HSQC)和电子轰击质谱(EI-MS)光谱数据确定了它们的化学结构。这些化合物以结构和浓度依赖的方式抑制肺癌A549细胞、结肠癌HT - 29细胞和神经胶质瘤C6细胞的增殖和活力。一些类似物的活性低于10 μmol dm−3(半数抑制浓度(IC50))。神经胶质瘤C6细胞对所测试的化合物最为敏感。一般来说，这些衍生物对皮肤成纤维细胞HSF培养物无毒。此外，其中一些对经处理的正常细胞具有保护作用。计算机模拟对化合物性质的评估表明，它们具有显著的类药物特性，并且大多数显示出低毒性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e03d/4498246/acf5d30e4ce6/706_2015_1453_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e03d/4498246/89e10ecebd8f/706_2015_1453_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e03d/4498246/bbd4e16b0507/706_2015_1453_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e03d/4498246/997588197743/706_2015_1453_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e03d/4498246/d39a81fb6fe2/706_2015_1453_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e03d/4498246/acf5d30e4ce6/706_2015_1453_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e03d/4498246/89e10ecebd8f/706_2015_1453_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e03d/4498246/bbd4e16b0507/706_2015_1453_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e03d/4498246/997588197743/706_2015_1453_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e03d/4498246/d39a81fb6fe2/706_2015_1453_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e03d/4498246/acf5d30e4ce6/706_2015_1453_Fig4_HTML.jpg

相似文献

1
Synthesis, characterization, and pharmacological evaluation of novel azolo- and azinothiazinones containing 2,4-dihydroxyphenyl substituent as anticancer agents.含2,4 - 二羟基苯基取代基的新型唑并噻嗪酮和氮杂噻嗪酮作为抗癌剂的合成、表征及药理评价
Monatsh Chem. 2015;146(8):1315-1327. doi: 10.1007/s00706-015-1453-4. Epub 2015 Apr 2.
2
Synthesis of 2-(2,4-dihydroxyphenyl)thieno-1,3-thiazin-4-ones, their lipophilicity and anticancer activity in vitro.2-(2,4-二羟基苯基)噻吩并-1,3-噻嗪-4-酮的合成、亲脂性及其体外抗癌活性
Mol Divers. 2015 Nov;19(4):725-36. doi: 10.1007/s11030-015-9599-x. Epub 2015 Apr 29.
3
Synthesis and anticancer activity of new 2-aryl-4h-3,1-benzothiazines.新型 2-芳基-4H-3,1-苯并噻嗪的合成及抗癌活性。
Arch Pharm (Weinheim). 2011 Apr;344(4):224-30. doi: 10.1002/ardp.201000228. Epub 2011 Jan 14.
4
Imidazole-Derived Alkyl and Aryl Ethers: Synthesis, Characterization, In Vitro Anticancer and Antioxidant Activities, Carbonic Anhydrase I-II Inhibition Properties, and In Silico Studies.咪唑衍生的烷基和芳基醚：合成、表征、体外抗癌和抗氧化活性、碳酸酐酶I-II抑制特性及计算机模拟研究
ACS Omega. 2024 May 3;9(19):20937-20956. doi: 10.1021/acsomega.4c00028. eCollection 2024 May 14.
5
Novel derivatives of methyl and ethyl 2-(4-oxo-8-aryl-2H-3,4,6,7-tetrahydroimidazo[2,1-c][1,2,4]triazin-3-yl)acetates from biologically active 1-aryl-2-hydrazinoimidazolines: synthesis, crystal structure and antiproliferative activity.基于生物活性1-芳基-2-肼基咪唑啉的新型2-(4-氧代-8-芳基-2H-3,4,6,7-四氢咪唑并[2,1-c][1,2,4]三嗪-3-基)乙酸甲酯和乙酯衍生物：合成、晶体结构及抗增殖活性
Eur J Med Chem. 2006 Dec;41(12):1373-84. doi: 10.1016/j.ejmech.2006.06.013. Epub 2006 Sep 22.
6
Synthesis of novel 4-(1H-benzimidazol-2-yl)benzene-1,3-diols and their cytotoxic activity against human cancer cell lines.新型 4-(1H-苯并咪唑-2-基)苯-1,3-二醇的合成及其对人癌细胞系的细胞毒性活性。
Arch Pharm Res. 2011 Oct;34(10):1639-47. doi: 10.1007/s12272-011-1008-0. Epub 2011 Nov 12.
7
New derivative of 2-(2,4-dihydroxyphenyl)thieno-1,3-thiazin-4-one (BChTT) elicits antiproliferative effect via p38-mediated cell cycle arrest in cancer cells.2-(2,4-二羟基苯基)噻吩并-1,3-噻嗪-4-酮（BChTT）的新型衍生物通过p38介导的癌细胞周期阻滞发挥抗增殖作用。
Bioorg Med Chem. 2016 Mar 15;24(6):1356-61. doi: 10.1016/j.bmc.2016.02.009. Epub 2016 Feb 6.
8
Synthesis and anticholinesterase activities of novel 1,3,4-thiadiazole based compounds.新型 1,3,4-噻二唑基化合物的合成及抗胆碱酯酶活性。
J Enzyme Inhib Med Chem. 2013 Aug;28(4):816-23. doi: 10.3109/14756366.2012.688041. Epub 2012 May 28.
9
SYNTHESIS AND BIOLOGICAL ACTIVITY OF NOVEL N,N-CYCLIC-2,4-DIHYDROXYTHIOBENZAMIDE DERIVATIVES.
Acta Pol Pharm. 2015 Sep-Oct;72(5):943-50.
10
Evaluation of antiproliferative effect in vitro of some 2-amino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole derivatives.某些2-氨基-5-（2,4-二羟基苯基）-1,3,4-噻二唑衍生物的体外抗增殖作用评估
Chem Pharm Bull (Tokyo). 2006 Jul;54(7):988-91. doi: 10.1248/cpb.54.988.

引用本文的文献

1
Investigation of 2,4-Dihydroxylaryl-Substituted Heterocycles as Inhibitors of the Growth and Development of Biotrophic Fungal Pathogens Associated with the Most Common Cereal Diseases.调查 2,4-二羟基芳基取代杂环作为与最常见谷物病害相关的生物营养性真菌病原体生长和发育抑制剂。
Int J Mol Sci. 2024 Jul 29;25(15):8262. doi: 10.3390/ijms25158262.

本文引用的文献

1
89Zr-trastuzumab and 89Zr-bevacizumab PET to evaluate the effect of the HSP90 inhibitor NVP-AUY922 in metastatic breast cancer patients.89Zr-曲妥珠单抗和 89Zr-贝伐珠单抗 PET 评估 HSP90 抑制剂 NVP-AUY922 对转移性乳腺癌患者的疗效。
Clin Cancer Res. 2014 Aug 1;20(15):3945-54. doi: 10.1158/1078-0432.CCR-14-0491.
2
Synthesis and evaluation of new Hsp90 inhibitors based on a 1,4,5-trisubstituted 1,2,3-triazole scaffold.基于 1,4,5-三取代 1,2,3-三唑骨架的新型 HSP90 抑制剂的合成与评价。
J Med Chem. 2014 Mar 27;57(6):2258-74. doi: 10.1021/jm401536b. Epub 2014 Mar 17.
3
Bioisosteric approach in designing new monastrol derivatives: an investigation on their ADMET prediction using in silico derived parameters.
采用生物等排原理设计新型单加氧酶抑制剂衍生物：基于计算机衍生参数的药物代谢预测研究。
J Mol Graph Model. 2013 Sep;45:202-10. doi: 10.1016/j.jmgm.2013.09.002. Epub 2013 Sep 12.
4
First-in-human phase I dose-escalation study of the HSP90 inhibitor AUY922 in patients with advanced solid tumors.人用 I 期剂量递增研究 HSP90 抑制剂 AUY922 在晚期实体瘤患者中的应用。
Clin Cancer Res. 2013 Jul 1;19(13):3671-80. doi: 10.1158/1078-0432.CCR-12-3404. Epub 2013 Jun 11.
5
Learning from nature: advances in geldanamycin- and radicicol-based inhibitors of Hsp90.从大自然中学习：新型格尔德霉素和雷帕霉素衍生物类 HSP90 抑制剂的研究进展
J Org Chem. 2013 Jun 7;78(11):5117-41. doi: 10.1021/jo4002849. Epub 2013 Mar 26.
6
Synthesis, biological evaluation, and molecular docking studies of cinnamic acyl 1,3,4-thiadiazole amide derivatives as novel antitubulin agents.合成、生物评价和分子对接研究肉桂酰 1,3,4-噻二唑酰胺衍生物作为新型抗微管蛋白剂。
Bioorg Med Chem. 2012 Feb 1;20(3):1181-7. doi: 10.1016/j.bmc.2011.12.057. Epub 2012 Jan 5.
7
One-pot synthesis of new (1,3-thiazolo[5,4-b]pyridin-2-yl)benzenediols and their antiproliferative activities against human cancer cell lines.一锅法合成新型（1,3-噻唑并[5,4-b]吡啶-2-基）苯二酚及其对人癌细胞系的抗增殖活性。
Chem Biodivers. 2012 Jan;9(1):48-57. doi: 10.1002/cbdv.201100007.
8
Synthesis and anticancer activity of new 2-aryl-4h-3,1-benzothiazines.新型 2-芳基-4H-3,1-苯并噻嗪的合成及抗癌活性。
Arch Pharm (Weinheim). 2011 Apr;344(4):224-30. doi: 10.1002/ardp.201000228. Epub 2011 Jan 14.
9
Targeting heat shock protein 72 enhances Hsp90 inhibitor-induced apoptosis in myeloma.靶向热休克蛋白72可增强热休克蛋白90抑制剂诱导的骨髓瘤细胞凋亡。
Leukemia. 2010 Oct;24(10):1804-7. doi: 10.1038/leu.2010.168. Epub 2010 Aug 12.
10
Novel benzimidazole-pyrimidine conjugates as potent antitumor agents.新型苯并咪唑-嘧啶化合物作为有效的抗肿瘤药物。
Eur J Med Chem. 2010 Jun;45(6):2336-44. doi: 10.1016/j.ejmech.2010.02.011. Epub 2010 Feb 13.