通过点击化学合成三唑及其药理应用的最新进展:综述。

IF 2.5 4区 医学 Q3 CHEMISTRY, MEDICINAL Bioorganic & Medicinal Chemistry Letters Pub Date : 2024-08-15 DOI:10.1016/j.bmcl.2024.129927
Riya Khandelwal, Mahesh Vasava, R.B. Abhirami, Manaswini Karsharma
{"title":"通过点击化学合成三唑及其药理应用的最新进展:综述。","authors":"Riya Khandelwal,&nbsp;Mahesh Vasava,&nbsp;R.B. Abhirami,&nbsp;Manaswini Karsharma","doi":"10.1016/j.bmcl.2024.129927","DOIUrl":null,"url":null,"abstract":"<div><p>Click chemistry is a flexible method featuring only the most feasible and efficient chemical reactions. The synthesis of 1,2,3-triazole from azides and terminal acetylenes using copper(I) as a catalyst is an extremely powerful reaction due to the extreme dependability, good selectivity, and biocompatibility of the starting materials. Triazole molecules are more than simple passive linkers; through hydrogen bonding and dipole interactions, they rapidly bind with biological targets. Its applications in drug development are expanding, ranging from target-oriented in situ chemistry and combinatorial mechanisms for lead generation to bioconjugation methods to study proteins and DNA. The click chemistry has frequently been used to speed up drug discovery and optimization processes in the past few years. The click chemistry reaction based on copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a biochemical process with applications in medicinal chemistry and chemical biology. Thus, click reactions are an essential component of the toolkit for medicinal chemistry and help medicinal chemists overcome the barriers in chemical reactions, increase throughput, and improve the standards of compound libraries. The review highlights the recent advancements in the copper-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry approach for synthesizing biologically important triazole moieties with a greater emphasis on synthesis methodologies and pharmacological applications. Additionally, the triazole-based FDA-approved drugs are also discussed with their mode of action to highlight the importance of the click chemistry approach in synthesizing the bioactive triazole compounds.</p></div>","PeriodicalId":256,"journal":{"name":"Bioorganic & Medicinal Chemistry Letters","volume":"112 ","pages":"Article 129927"},"PeriodicalIF":2.5000,"publicationDate":"2024-08-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Recent advances in triazole synthesis via click chemistry and their pharmacological applications: A review\",\"authors\":\"Riya Khandelwal,&nbsp;Mahesh Vasava,&nbsp;R.B. Abhirami,&nbsp;Manaswini Karsharma\",\"doi\":\"10.1016/j.bmcl.2024.129927\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Click chemistry is a flexible method featuring only the most feasible and efficient chemical reactions. The synthesis of 1,2,3-triazole from azides and terminal acetylenes using copper(I) as a catalyst is an extremely powerful reaction due to the extreme dependability, good selectivity, and biocompatibility of the starting materials. Triazole molecules are more than simple passive linkers; through hydrogen bonding and dipole interactions, they rapidly bind with biological targets. Its applications in drug development are expanding, ranging from target-oriented in situ chemistry and combinatorial mechanisms for lead generation to bioconjugation methods to study proteins and DNA. The click chemistry has frequently been used to speed up drug discovery and optimization processes in the past few years. The click chemistry reaction based on copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a biochemical process with applications in medicinal chemistry and chemical biology. Thus, click reactions are an essential component of the toolkit for medicinal chemistry and help medicinal chemists overcome the barriers in chemical reactions, increase throughput, and improve the standards of compound libraries. The review highlights the recent advancements in the copper-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry approach for synthesizing biologically important triazole moieties with a greater emphasis on synthesis methodologies and pharmacological applications. Additionally, the triazole-based FDA-approved drugs are also discussed with their mode of action to highlight the importance of the click chemistry approach in synthesizing the bioactive triazole compounds.</p></div>\",\"PeriodicalId\":256,\"journal\":{\"name\":\"Bioorganic & Medicinal Chemistry Letters\",\"volume\":\"112 \",\"pages\":\"Article 129927\"},\"PeriodicalIF\":2.5000,\"publicationDate\":\"2024-08-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Bioorganic & Medicinal Chemistry Letters\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0960894X24003299\",\"RegionNum\":4,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bioorganic & Medicinal Chemistry Letters","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0960894X24003299","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0

摘要

点击化学是一种灵活的方法,只进行最可行、最有效的化学反应。以铜(I)为催化剂,从叠氮化物和末端乙炔基合成 1,2,3-三氮唑是一种极其有效的反应,因为起始材料极其可靠,具有良好的选择性和生物相容性。三唑分子不仅仅是简单的被动连接剂,通过氢键和偶极相互作用,它们还能迅速与生物靶标结合。它在药物开发中的应用正在不断扩大,从以靶点为导向的原位化学和用于先导物生成的组合机制,到用于蛋白质和 DNA 研究的生物结合方法,不一而足。在过去几年中,点击化学被频繁用于加速药物发现和优化过程。基于铜催化叠氮-炔环加成(CuAAC)的点击化学反应是一种生物化学过程,可应用于药物化学和化学生物学。因此,点击反应是药物化学工具包的重要组成部分,有助于药物化学家克服化学反应中的障碍,提高通量,并改善化合物库的标准。这篇综述重点介绍了铜催化叠氮-炔环加成(CuAAC)点击化学方法在合成具有重要生物意义的三唑分子方面的最新进展,并更加强调了合成方法和药理应用。此外,还讨论了美国 FDA 批准的基于三唑的药物及其作用模式,以突出点击化学方法在合成具有生物活性的三唑化合物方面的重要性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

摘要图片

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
Recent advances in triazole synthesis via click chemistry and their pharmacological applications: A review

Click chemistry is a flexible method featuring only the most feasible and efficient chemical reactions. The synthesis of 1,2,3-triazole from azides and terminal acetylenes using copper(I) as a catalyst is an extremely powerful reaction due to the extreme dependability, good selectivity, and biocompatibility of the starting materials. Triazole molecules are more than simple passive linkers; through hydrogen bonding and dipole interactions, they rapidly bind with biological targets. Its applications in drug development are expanding, ranging from target-oriented in situ chemistry and combinatorial mechanisms for lead generation to bioconjugation methods to study proteins and DNA. The click chemistry has frequently been used to speed up drug discovery and optimization processes in the past few years. The click chemistry reaction based on copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a biochemical process with applications in medicinal chemistry and chemical biology. Thus, click reactions are an essential component of the toolkit for medicinal chemistry and help medicinal chemists overcome the barriers in chemical reactions, increase throughput, and improve the standards of compound libraries. The review highlights the recent advancements in the copper-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry approach for synthesizing biologically important triazole moieties with a greater emphasis on synthesis methodologies and pharmacological applications. Additionally, the triazole-based FDA-approved drugs are also discussed with their mode of action to highlight the importance of the click chemistry approach in synthesizing the bioactive triazole compounds.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
CiteScore
5.70
自引率
3.70%
发文量
463
审稿时长
27 days
期刊介绍: Bioorganic & Medicinal Chemistry Letters presents preliminary experimental or theoretical research results of outstanding significance and timeliness on all aspects of science at the interface of chemistry and biology and on major advances in drug design and development. The journal publishes articles in the form of communications reporting experimental or theoretical results of special interest, and strives to provide maximum dissemination to a large, international audience.
期刊最新文献
Design and evaluation of novel N-substituent diphenylamine derivatives as tubulin colchicine binding site inhibitors. Cell penetrable peptide nucleic acids targeting PDZK1IP1 with anti-inflammatory potential in human keratinocytes. Grafting a chromophore on AMD070 analogues for CXCR4 bioimaging: Chemical synthesis and in vitro assessment of the inhibition properties of the CXCR4 receptor. Editorial Board Contents continued
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1