• 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

具有酪氨酸酶和脲酶抑制活性的手性吡唑并[4,3-e][1,2,4]三嗪磺酰胺的合成

Synthesis of chiral pyrazolo[4,3-e][1,2,4]triazine sulfonamides with tyrosinase and urease inhibitory activity.

作者信息

Mojzych Mariusz, Tarasiuk Paweł, Kotwica-Mojzych Katarzyna, Rafiq Muhammad, Seo Sung-Yum, Nicewicz Michał, Fornal Emilia

机构信息

a Department of Physico-Chemical Hazards of Health and Ecology , Institute of Rural Health , Lublin , Poland.

b Department of Chemistry , Siedlce University of Natural Sciences and Humanities , Siedlce , Poland.

出版信息

J Enzyme Inhib Med Chem. 2017 Dec;32(1):99-105. doi: 10.1080/14756366.2016.1238362. Epub 2016 Oct 25.

DOI:10.1080/14756366.2016.1238362
PMID:27778522
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6010123/
Abstract

A new series of sulfonamide derivatives of pyrazolo[4,3-e][1,2,4]triazine with chiral amino group has been synthesized and characterized. The compounds were tested for their tyrosinase and urease inhibitory activity. Evaluation of prepared derivatives demonstrated that compounds (8b) and (8j) are most potent mushroom tyrosinase inhibitors whereas all of the obtained compounds showed higher urease inhibitory activity than the standard thiourea. The compounds (8a), (8f) and (8i) exhibited excellent enzyme inhibitory activity with IC 0.037, 0.044 and 0.042 μM, respectively, while IC of thiourea is 20.9 μM.

摘要

合成并表征了一系列新型含手性氨基的吡唑并[4,3-e][1,2,4]三嗪磺酰胺衍生物。测试了这些化合物的酪氨酸酶和脲酶抑制活性。对所制备衍生物的评估表明，化合物(8b)和(8j)是最有效的蘑菇酪氨酸酶抑制剂，而所有获得的化合物均显示出比标准硫脲更高的脲酶抑制活性。化合物(8a)、(8f)和(8i)分别表现出优异的酶抑制活性，其IC50分别为0.037、0.044和0.042 μM，而硫脲的IC50为20.9 μM。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a6f/6010123/9201049c9888/IENZ_A_1238362_F0003_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a6f/6010123/2d6f443efeed/IENZ_A_1238362_SCH0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a6f/6010123/86d2f4793fd0/IENZ_A_1238362_F0001_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a6f/6010123/4d6b2d470849/IENZ_A_1238362_F0002_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a6f/6010123/9201049c9888/IENZ_A_1238362_F0003_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a6f/6010123/2d6f443efeed/IENZ_A_1238362_SCH0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a6f/6010123/86d2f4793fd0/IENZ_A_1238362_F0001_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a6f/6010123/4d6b2d470849/IENZ_A_1238362_F0002_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a6f/6010123/9201049c9888/IENZ_A_1238362_F0003_C.jpg

相似文献

1
Synthesis of chiral pyrazolo[4,3-e][1,2,4]triazine sulfonamides with tyrosinase and urease inhibitory activity.具有酪氨酸酶和脲酶抑制活性的手性吡唑并[4,3-e][1,2,4]三嗪磺酰胺的合成
J Enzyme Inhib Med Chem. 2017 Dec;32(1):99-105. doi: 10.1080/14756366.2016.1238362. Epub 2016 Oct 25.
2
Synthesis of pyrazolo[4,3-e][1,2,4]triazine sulfonamides, novel Sildenafil analogs with tyrosinase inhibitory activity.吡唑并[4,3-e][1,2,4]三嗪磺酰胺的合成，具有酪氨酸酶抑制活性的新型西地那非类似物。
Bioorg Med Chem. 2014 Dec 1;22(23):6616-6624. doi: 10.1016/j.bmc.2014.10.009.
3
Jack Bean Urease Inhibitors, and Antioxidant Activity Based on Palmitic acid Derived 1-acyl-3- Arylthioureas: Synthesis, Kinetic Mechanism and Molecular Docking Studies.基于棕榈酸衍生的1-酰基-3-芳基硫脲的杰克豆脲酶抑制剂及其抗氧化活性：合成、动力学机制和分子对接研究
Drug Res (Stuttg). 2017 Oct;67(10):596-605. doi: 10.1055/s-0043-113832. Epub 2017 Jul 3.
4
Design and synthesis of 3,5-diaryl-4,5-dihydro-1H-pyrazoles as new tyrosinase inhibitors.设计和合成 3,5-二芳基-4,5-二氢-1H-吡唑作为新型酪氨酸酶抑制剂。
Bioorg Med Chem. 2013 Apr 1;21(7):2156-62. doi: 10.1016/j.bmc.2012.12.054. Epub 2013 Jan 11.
5
Synthesis and kinase inhibitory activity of new sulfonamide derivatives of pyrazolo[4,3-e][1,2,4]triazines.新型吡唑并[4,3-e][1,2,4]三嗪磺酰胺衍生物的合成及激酶抑制活性。
Eur J Med Chem. 2014 May 6;78:217-24. doi: 10.1016/j.ejmech.2014.03.054. Epub 2014 Mar 18.
6
Synthesis, Antioxidant and In-Silico Studies of Potent Urease Inhibitors: N-(4-{[(4-Methoxyphenethyl)-(substituted)amino]sulfonyl}phenyl)acetamides.强效脲酶抑制剂的合成、抗氧化及计算机模拟研究：N-(4-{[(4-甲氧基苯乙基)-(取代)氨基]磺酰基}苯基)乙酰胺
Drug Res (Stuttg). 2019 Feb;69(2):111-120. doi: 10.1055/a-0654-5074. Epub 2018 Aug 7.
7
Synthesis and tyrosinase inhibitory properties of novel isoquinoline urea/thiourea derivatives.新型异喹啉脲/硫脲衍生物的合成及酪氨酸酶抑制活性。
Artif Cells Nanomed Biotechnol. 2014 Jun;42(3):178-85. doi: 10.3109/10731199.2013.785953. Epub 2013 Apr 16.
8
Synthesis and biological evaluation of polyhydroxy benzophenone as mushroom tyrosinase inhibitors.聚羟基二苯甲酮类化合物的合成及其对蘑菇酪氨酸酶的抑制活性评价。
J Enzyme Inhib Med Chem. 2011 Jun;26(3):449-52. doi: 10.3109/14756366.2010.521745. Epub 2010 Oct 13.
9
Design, synthesis, kinetic mechanism and molecular docking studies of novel 1-pentanoyl-3-arylthioureas as inhibitors of mushroom tyrosinase and free radical scavengers.新型1-戊酰基-3-芳基硫脲作为蘑菇酪氨酸酶抑制剂和自由基清除剂的设计、合成、动力学机制及分子对接研究
Eur J Med Chem. 2017 Dec 1;141:273-281. doi: 10.1016/j.ejmech.2017.09.059. Epub 2017 Sep 29.
10
Azomethines, isoxazole, N-substituted pyrazoles and pyrimidine containing curcumin derivatives: Urease inhibition and molecular modeling studies.偶氮甲碱、异恶唑、N-取代吡唑和含嘧啶的姜黄素衍生物：脲酶抑制作用及分子模拟研究
Biochem Biophys Res Commun. 2017 Aug 19;490(2):434-440. doi: 10.1016/j.bbrc.2017.06.059. Epub 2017 Jun 13.

引用本文的文献

1
Synthesis, anticancer evaluation, and electrochemical investigation of new chiral pyrazolo[4,3-e]tetrazolo[1,5-b][1,2,4]triazine sulfonamides.新型手性吡唑并[4,3-e]四唑并[1,5-b][1,2,4]三嗪磺酰胺的合成、抗癌活性评价及电化学研究
Sci Rep. 2025 May 28;15(1):18640. doi: 10.1038/s41598-025-02835-w.
2
Evaluation of Tyrosinase Inhibitory Activity of Carbathioamidopyrazoles and Their Potential Application in Cosmetic Products and Melanoma Treatment.碳硫酰胺基吡唑类化合物的酪氨酸酶抑制活性评估及其在化妆品和黑色素瘤治疗中的潜在应用
Int J Mol Sci. 2025 Apr 19;26(8):3882. doi: 10.3390/ijms26083882.
3
2,5-Dihydroxyphenylethanone: an anti-melanogenic bioactive compound isolated from .

本文引用的文献

1
Iminothiazoline-Sulfonamide Hybrids as Jack Bean Urease Inhibitors; Synthesis, Kinetic Mechanism and Computational Molecular Modeling.亚氨基噻唑啉-磺酰胺杂化物作为刀豆脲酶抑制剂：合成、动力学机制及计算分子建模
Chem Biol Drug Des. 2016 Mar;87(3):434-43. doi: 10.1111/cbdd.12675. Epub 2015 Nov 26.
2
Relaxant effects of selected sildenafil analogues in the rat aorta.所选西地那非类似物对大鼠主动脉的舒张作用。
J Enzyme Inhib Med Chem. 2016;31(3):381-8. doi: 10.3109/14756366.2015.1024674. Epub 2015 Mar 23.
3
Design, synthesis and bioevaluation of novel umbelliferone analogues as potential mushroom tyrosinase inhibitors.
2,5-二羟基苯乙酮：一种从……中分离出的抗黑素生成生物活性化合物。
J Enzyme Inhib Med Chem. 2025 Dec;40(1):2495364. doi: 10.1080/14756366.2025.2495364. Epub 2025 Apr 29.
4
Investigation of the In Vitro Antioxidant, Anticholinesterase, Antiurease, Antityrosinase, and Cytotoxic Properties of a Novel Compound: 4-Methoxy-2-(4-Methoxyphenyl)Benzo[d][1,3,2]Dioxaborole.新型化合物4-甲氧基-2-(4-甲氧基苯基)苯并[d][1,3,2]二氧硼烷的体外抗氧化、抗胆碱酯酶、抗脲酶、抗酪氨酸酶及细胞毒性特性研究
Pharmacol Res Perspect. 2025 Feb;13(1):e70044. doi: 10.1002/prp2.70044.
5
Exploring Acyl Thiotriazinoindole Based Pharmacophores: Design, Synthesis, and SAR Studies with Molecular Docking and Biological Activity Profiling against Urease, α-amylase, α-glucosidase, Antimicrobial, and Antioxidant Targets.探索基于酰基硫代三嗪并吲哚的药效团：设计、合成及构效关系研究，采用分子对接技术对尿素酶、α-淀粉酶、α-葡萄糖苷酶进行生物活性谱分析，以及对抗菌和抗氧化靶点的研究。
Protein J. 2024 Oct;43(5):1009-1024. doi: 10.1007/s10930-024-10229-6. Epub 2024 Sep 2.
6
Novel synthesis of new triazine sulfonamides with antitumor, anti-microbial and anti-SARS-CoV-2 activities.具有抗肿瘤、抗菌和抗SARS-CoV-2活性的新型三嗪磺酰胺的合成
BMC Chem. 2024 Mar 26;18(1):58. doi: 10.1186/s13065-024-01164-9.
7
Genotoxicity of Novel Pyrazolo[4,3-]tetrazolo[1,5-][1,2,4]triazine Sulfonamides in Normal and Cancer Cells In Vitro.新型吡唑并[4,3-]四唑并[1,5-][1,2,4]三嗪磺酰胺类化合物在正常和癌细胞中的遗传毒性研究。
Int J Mol Sci. 2023 Feb 17;24(4):4053. doi: 10.3390/ijms24044053.
8
Cephalosporin as Potent Urease and Tyrosinase Inhibitor: Exploration through Enzyme Inhibition, Kinetic Mechanism, and Molecular Docking Studies.头孢菌素作为有效的脲酶和酪氨酸酶抑制剂：通过酶抑制、动力学机制和分子对接研究的探索。
Biomed Res Int. 2022 Jul 28;2022:1092761. doi: 10.1155/2022/1092761. eCollection 2022.
9
Pyrazolo[4,3-]tetrazolo[1,5-][1,2,4]triazine Sulfonamides as Novel Potential Anticancer Agents: Cytotoxic and Genotoxic Activities In Vitro.吡唑并[4,3-d]四唑并[1,5-a][1,2,4]三嗪磺酰胺类化合物作为新型潜在的抗癌剂：体外细胞毒性和遗传毒性活性。
Molecules. 2022 Jun 11;27(12):3761. doi: 10.3390/molecules27123761.
10
Preparation of Novel Pyrazolo[4,3-]tetrazolo[1,5-][1,2,4]triazine Sulfonamides and Their Experimental and Computational Biological Studies.新型吡唑并[4,3-]四唑并[1,5-][1,2,4]三嗪磺酰胺的制备及其实验和计算生物学研究。
Int J Mol Sci. 2022 May 24;23(11):5892. doi: 10.3390/ijms23115892.
新型伞形酮类似物作为潜在蘑菇酪氨酸酶抑制剂的设计、合成及生物活性评价
J Enzyme Inhib Med Chem. 2015 Dec;30(6):874-83. doi: 10.3109/14756366.2014.979346. Epub 2015 Feb 3.
4
Synthesis of pyrazolo[4,3-e][1,2,4]triazine sulfonamides, novel Sildenafil analogs with tyrosinase inhibitory activity.吡唑并[4,3-e][1,2,4]三嗪磺酰胺的合成，具有酪氨酸酶抑制活性的新型西地那非类似物。
Bioorg Med Chem. 2014 Dec 1;22(23):6616-6624. doi: 10.1016/j.bmc.2014.10.009.
5
Structure-activity relationships of the thujaplicins for inhibition of human tyrosinase.崖柏素对人酪氨酸酶抑制作用的构效关系
Bioorg Med Chem. 2014 Nov 1;22(21):6193-200. doi: 10.1016/j.bmc.2014.08.027. Epub 2014 Sep 21.
6
Synthesis and structure-activity relationship of thiobarbituric acid derivatives as potent inhibitors of urease.硫代巴比妥酸衍生物作为脲酶有效抑制剂的合成及构效关系
Bioorg Med Chem. 2014 Aug 1;22(15):4119-23. doi: 10.1016/j.bmc.2014.05.057. Epub 2014 Jun 2.
7
Effect of p-aminophenols on tyrosinase activity.对氨基苯酚对酪氨酸酶活性的影响。
Bioorg Med Chem. 2014 Aug 1;22(15):3994-4000. doi: 10.1016/j.bmc.2014.05.073. Epub 2014 Jun 11.
8
Design, synthesis and biological evaluation of hydroxy- or methoxy-substituted 5-benzylidene(thio) barbiturates as novel tyrosinase inhibitors.新型酪氨酸酶抑制剂——羟基或甲氧基取代的5-亚苄基（硫代）巴比妥酸盐的设计、合成及生物学评价
Bioorg Med Chem. 2014 Jul 1;22(13):3279-84. doi: 10.1016/j.bmc.2014.04.060. Epub 2014 May 15.
9
Pyrazolo[4,3-e][1,2,4]triazine sulfonamides as carbonic anhydrase inhibitors with antitumor activity.吡唑并[4,3 - e][1,2,4]三嗪磺酰胺类化合物作为具有抗肿瘤活性的碳酸酐酶抑制剂
Bioorg Med Chem. 2014 May 1;22(9):2643-7. doi: 10.1016/j.bmc.2014.03.029. Epub 2014 Mar 27.
10
Inhibitory effects of novel synthetic methimazole derivatives on mushroom tyrosinase and melanogenesis.新型合成甲巯咪唑衍生物对蘑菇酪氨酸酶和黑色素生成的抑制作用。
Bioorg Med Chem. 2014 May 1;22(9):2809-15. doi: 10.1016/j.bmc.2014.03.009. Epub 2014 Mar 15.