• 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

高活性 1-1,2,3-三唑键合色酮-甲硝唑偶联物抗厌氧食源性、水源性和性传播原生动物寄生虫。

Highly Potent 1-1,2,3-Triazole-Tethered Isatin-Metronidazole Conjugates Against Anaerobic Foodborne, Waterborne, and Sexually-Transmitted Protozoal Parasites.

机构信息

Department of Chemistry, Guru Nanak Dev University, Amritsar, India.

Center for Discovery and Innovation in Parasitic Diseases, Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, CA, United States.

出版信息

Front Cell Infect Microbiol. 2018 Oct 30;8:380. doi: 10.3389/fcimb.2018.00380. eCollection 2018.

DOI:10.3389/fcimb.2018.00380
PMID:30425970
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6218680/
Abstract

Parasitic infections like amebiasis, trichomoniasis, and giardiasis are major health threats in tropical and subtropical regions of the world. Metronidazole (MTZ) is the current drug of choice for amebiasis, giardiasis, and trichomoniasis but it has several adverse effects and potential resistance is a concern. In order to develop alternative antimicrobials, a library of 1-1,2,3-triazole-tethered metronidazole-isatin conjugates was synthesized using Huisgen's azide-alkyne cycloaddition reaction and evaluated for their amebicidal, anti-trichomonal, and anti-giardial potential. Most of the synthesized conjugates exhibited activities against , and . While activities against and were comparable to that of the standard drug MTZ, better activities were observed against and . Conjugates and were found to be 2-3-folds more potent than MTZ against and 8-16-folds more potent than MTZ against . Further analysis of these compounds on fungi and bacteria did not show inhibitory activity, demonstrating their specific anti-protozoal properties.

摘要

寄生虫感染，如阿米巴病、滴虫病和贾第虫病，是世界热带和亚热带地区的主要健康威胁。甲硝唑（MTZ）是目前治疗阿米巴病、贾第虫病和滴虫病的首选药物，但它有几种不良反应，而且存在潜在的耐药性问题。为了开发替代的抗菌药物，我们使用 Huisgen 的叠氮-炔环加成反应合成了一个 1-1,2,3-三唑键合甲硝唑-靛红缀合物库，并评估了它们的杀阿米巴、抗滴虫和抗贾第鞭毛虫的潜力。大多数合成的缀合物对 和 具有活性。虽然对 和 的活性与标准药物 MTZ 相当，但对 和 的活性更好。化合物 和 对 和 的活性比 MTZ 强 2-3 倍，比 MTZ 强 8-16 倍。对这些化合物在真菌和细菌上的进一步分析显示没有抑制活性，表明它们具有特定的抗原生动物特性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/fecfa2071d0d/fcimb-08-00380-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/2f83e2773cd5/fcimb-08-00380-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/3c30864a89f9/fcimb-08-00380-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/9cf4b27a2637/fcimb-08-00380-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/d7508f4ebad2/fcimb-08-00380-g0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/a15254430d34/fcimb-08-00380-g0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/ff00c570fba0/fcimb-08-00380-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/fecfa2071d0d/fcimb-08-00380-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/2f83e2773cd5/fcimb-08-00380-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/3c30864a89f9/fcimb-08-00380-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/9cf4b27a2637/fcimb-08-00380-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/d7508f4ebad2/fcimb-08-00380-g0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/a15254430d34/fcimb-08-00380-g0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/ff00c570fba0/fcimb-08-00380-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/da56/6218680/fecfa2071d0d/fcimb-08-00380-g0004.jpg

相似文献

1
Highly Potent 1-1,2,3-Triazole-Tethered Isatin-Metronidazole Conjugates Against Anaerobic Foodborne, Waterborne, and Sexually-Transmitted Protozoal Parasites.高活性 1-1,2,3-三唑键合色酮-甲硝唑偶联物抗厌氧食源性、水源性和性传播原生动物寄生虫。
Front Cell Infect Microbiol. 2018 Oct 30;8:380. doi: 10.3389/fcimb.2018.00380. eCollection 2018.
2
In vitro effect of nitazoxanide against Entamoeba histolytica, Giardia intestinalis and Trichomonas vaginalis trophozoites.硝唑尼特对溶组织内阿米巴、肠贾第虫和阴道毛滴虫滋养体的体外作用。
J Eukaryot Microbiol. 2002 May-Jun;49(3):201-8. doi: 10.1111/j.1550-7408.2002.tb00523.x.
3
Drug susceptibility testing in microaerophilic parasites: Cysteine strongly affects the effectivities of metronidazole and auranofin, a novel and promising antimicrobial.微需氧寄生虫的药物敏感性检测：半胱氨酸强烈影响甲硝唑和金诺芬（一种新型、有前途的抗菌药物）的疗效。
Int J Parasitol Drugs Drug Resist. 2017 Dec;7(3):321-327. doi: 10.1016/j.ijpddr.2017.09.001. Epub 2017 Sep 5.
4
Design, synthesis and in vitro antiprotozoal activity of benzimidazole-pentamidine hybrids.苯并咪唑-喷他脒杂合物的设计、合成及体外抗寄生虫活性
Bioorg Med Chem Lett. 2008 Jun 1;18(11):3147-51. doi: 10.1016/j.bmcl.2008.05.009. Epub 2008 May 4.
5
Metronidazole-triazole conjugates: activity against Clostridium difficile and parasites.甲硝唑-三唑缀合物：对艰难梭菌和寄生虫的活性。
Eur J Med Chem. 2015 Aug 28;101:96-102. doi: 10.1016/j.ejmech.2015.06.019. Epub 2015 Jun 18.
6
Nitroimidazole carboxamides as antiparasitic agents targeting Giardia lamblia, Entamoeba histolytica and Trichomonas vaginalis.硝基咪唑甲酰胺作为针对蓝氏贾第鞭毛虫、溶组织内阿米巴和阴道毛滴虫的抗寄生虫药物。
Eur J Med Chem. 2016 Sep 14;120:353-62. doi: 10.1016/j.ejmech.2016.04.064. Epub 2016 Apr 27.
7
In vitro activity of nitazoxanide and related compounds against isolates of Giardia intestinalis, Entamoeba histolytica and Trichomonas vaginalis.硝唑尼特及相关化合物对肠道贾第虫、溶组织内阿米巴和阴道毛滴虫分离株的体外活性。
J Antimicrob Chemother. 2002 Jan;49(1):103-11. doi: 10.1093/jac/49.1.103.
8
Efficacy of new 5-nitroimidazoles against metronidazole-susceptible and -resistant Giardia, Trichomonas, and Entamoeba spp.新型5-硝基咪唑类药物对甲硝唑敏感及耐药的贾第虫、滴虫和内阿米巴属的疗效
Antimicrob Agents Chemother. 1999 Jan;43(1):73-6. doi: 10.1128/AAC.43.1.73.
9
Synthesis of 3-tetrazolylmethyl-4H-chromen-4-ones via Ugi-azide and biological evaluation against Entamoeba histolytica, Giardia lamblia and Trichomona vaginalis.通过Ugi-叠氮化物合成3-四唑基甲基-4H-色烯-4-酮及其对溶组织内阿米巴、蓝氏贾第鞭毛虫和阴道毛滴虫的生物学评价
Bioorg Med Chem. 2014 Feb 15;22(4):1370-6. doi: 10.1016/j.bmc.2013.12.069. Epub 2014 Jan 11.
10
Drug targets and mechanisms of resistance in the anaerobic protozoa.厌氧原生动物中的药物靶点与耐药机制
Clin Microbiol Rev. 2001 Jan;14(1):150-64. doi: 10.1128/CMR.14.1.150-164.2001.

引用本文的文献

1
Synthesis, In-Silico Molecular Docking Studies, and In-Vitro Antimicrobial Evaluation of Isatin Scaffolds bearing 1, 2, 3-Triazoles using Click Chemistry.利用点击化学对含1,2,3-三唑的异吲哚酮骨架进行合成、计算机辅助分子对接研究及体外抗菌评估
Indian J Microbiol. 2025 Mar;65(1):405-423. doi: 10.1007/s12088-024-01264-z. Epub 2024 Apr 3.
2
An Unusual U2AF2 Inhibits Splicing and Attenuates the Virulence of the Human Protozoan Parasite .一种异常的 U2AF2 抑制剪接并减弱人类原生动物寄生虫的毒力。
Front Cell Infect Microbiol. 2022 Jun 17;12:888428. doi: 10.3389/fcimb.2022.888428. eCollection 2022.
3
An Overview of Mucosa-Associated Protozoa: Challenges in Chemotherapy and Future Perspectives.

本文引用的文献

1
Azide-Alkyne Cycloaddition En Route to 1-1,2,3-Triazole-Tethered Isatin-Ferrocene, Ferrocenylmethoxy-Isatin, and Isatin-Ferrocenylchalcone Conjugates: Synthesis and Antiproliferative Evaluation.通过叠氮化物-炔烃环加成反应合成1,2,3-三唑连接的异吲哚酮-二茂铁、二茂铁基甲氧基-异吲哚酮和异吲哚酮-二茂铁基查尔酮共轭物：合成与抗增殖评估。
ACS Omega. 2018 Jan 31;3(1):1263-1268. doi: 10.1021/acsomega.7b01755. Epub 2018 Jan 30.
2
Larrea tridentata: A novel source for anti-parasitic agents active against Entamoeba histolytica, Giardia lamblia and Naegleria fowleri.三齿拉瑞阿：一种对抗溶组织内阿米巴、蓝氏贾第鞭毛虫和福氏耐格里变形虫具有活性的抗寄生虫剂的新来源。
PLoS Negl Trop Dis. 2017 Aug 9;11(8):e0005832. doi: 10.1371/journal.pntd.0005832. eCollection 2017 Aug.
3
黏膜相关原生动物概述：化疗的挑战与未来展望。
Front Cell Infect Microbiol. 2022 Apr 25;12:860442. doi: 10.3389/fcimb.2022.860442. eCollection 2022.
4
Diastereoselective approach to rationally design tetrahydro-β-carboline-isatin conjugates as potential SERMs against breast cancer.用于合理设计四氢-β-咔啉-异吲哚酮缀合物作为抗乳腺癌潜在选择性雌激素受体调节剂的非对映选择性方法。
RSC Adv. 2019 Mar 28;9(17):9809-9819. doi: 10.1039/c9ra00744j. eCollection 2019 Mar 22.
4-Aminoquinoline-chalcone/-N-acetylpyrazoline conjugates: Synthesis and antiplasmodial evaluation.4-氨基喹啉-查尔酮/-N-乙酰吡唑啉缀合物的合成及抗疟原虫活性评价。
Eur J Med Chem. 2017 Sep 29;138:993-1001. doi: 10.1016/j.ejmech.2017.07.041. Epub 2017 Jul 22.
4
Synthetic siRNAs effectively target cystein protease 12 and α-actinin transcripts in Trichomonas vaginalis.合成的小干扰RNA（siRNAs）可有效靶向阴道毛滴虫中的半胱氨酸蛋白酶12和α-辅肌动蛋白转录本。
Exp Parasitol. 2015 Oct;157:30-4. doi: 10.1016/j.exppara.2015.06.012. Epub 2015 Jun 29.
5
Synthesis and antiprotozoal activity of mono- and bis-uracil isatin conjugates against the human pathogen Trichomonas vaginalis.单尿嘧啶和双尿嘧啶异吲哚酮缀合物对人类病原体阴道毛滴虫的合成及其抗原生动物活性
Bioorg Med Chem. 2015 Aug 15;23(16):5190-7. doi: 10.1016/j.bmc.2015.04.075. Epub 2015 May 6.
6
Gene-expression analysis of cold-stress response in the sexually transmitted protist Trichomonas vaginalis.性传播原生生物阴道毛滴虫冷应激反应的基因表达分析。
J Microbiol Immunol Infect. 2015 Dec;48(6):662-75. doi: 10.1016/j.jmii.2014.07.013. Epub 2014 Nov 1.
7
Potentiating Metronidazole Scaffold against Resistant Trichomonas: Design, Synthesis, Biology and 3D-QSAR Analysis.增强甲硝唑支架对耐药滴虫的作用：设计、合成、生物学及三维定量构效关系分析
ACS Med Chem Lett. 2011 Dec 16;3(2):83-7. doi: 10.1021/ml200161t. eCollection 2012 Feb 9.
8
N-Propargylated isatin-Mannich mono- and bis-adducts: synthesis and preliminary analysis of in vitro activity against Tritrichomonas foetus.N-炔丙基异吲哚酮-曼尼希单加合物和双加合物：合成及其对胎儿三毛滴虫体外活性的初步分析
Eur J Med Chem. 2014 Mar 3;74:657-63. doi: 10.1016/j.ejmech.2014.01.015. Epub 2014 Jan 18.
9
Extra-intestinal and long term consequences of Giardia duodenalis infections.贾第虫属感染的肠外和长期后果。
World J Gastroenterol. 2013 Dec 21;19(47):8974-85. doi: 10.3748/wjg.v19.i47.8974.
10
Getting trichy: tools and approaches to interrogating Trichomonas vaginalis in a post-genome world.了解滴虫：在后基因组时代探究阴道毛滴虫的工具和方法。
Trends Parasitol. 2013 Jan;29(1):17-25. doi: 10.1016/j.pt.2012.10.004. Epub 2012 Dec 5.