N-Iodosuccinimide-Promoted Synthesis of Indolo[3,2-c]quinolizines via Cascade Intramolecular C–N Bond Formation/Aromatization with 3-(1H-Indol-3-yl)-2-(pyridin-2-yl)propanoates

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2025-04-10 DOI:10.1021/acs.joc.4c03039
Chen Chen, Xixiang Yang, Jiaxin Wang, Weiya Kong, Jianjun Chen, Xiaodong Tang
{"title":"N-Iodosuccinimide-Promoted Synthesis of Indolo[3,2-c]quinolizines via Cascade Intramolecular C–N Bond Formation/Aromatization with 3-(1H-Indol-3-yl)-2-(pyridin-2-yl)propanoates","authors":"Chen Chen, Xixiang Yang, Jiaxin Wang, Weiya Kong, Jianjun Chen, Xiaodong Tang","doi":"10.1021/acs.joc.4c03039","DOIUrl":null,"url":null,"abstract":"An NIS-promoted cascade of intramolecular C–N bond formation/aromatization with 3-(1<i>H</i>-indol-3-yl)-2-(pyridin-2-yl)propanoates is described for synthesizing a polycyclic indole skeleton, indolo[3,2-<i>c</i>]quinolizine, as well as 1,9-dihydropyrazolo[4’,3′:5,6]pyrido[2,3-<i>b</i>]indole. The advantages of this protocol include accessible starting materials, mild conditions, simple operation, and good yields. Indolo[3,2-<i>c</i>]quinolizines exhibited good fluorescence properties and effective staining for live cells, targeting lysosomes and mitochondria. Additionally, the products showed significant antiproliferative activity against tumor cells in the MTT assay.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"74 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c03039","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

An NIS-promoted cascade of intramolecular C–N bond formation/aromatization with 3-(1H-indol-3-yl)-2-(pyridin-2-yl)propanoates is described for synthesizing a polycyclic indole skeleton, indolo[3,2-c]quinolizine, as well as 1,9-dihydropyrazolo[4’,3′:5,6]pyrido[2,3-b]indole. The advantages of this protocol include accessible starting materials, mild conditions, simple operation, and good yields. Indolo[3,2-c]quinolizines exhibited good fluorescence properties and effective staining for live cells, targeting lysosomes and mitochondria. Additionally, the products showed significant antiproliferative activity against tumor cells in the MTT assay.

Abstract Image

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
n-碘琥珀酰亚胺促进3-(1h -吲哚-3-基)-2-(吡啶-2-基)丙烷级联形成分子内C-N键/芳构化合成吲哚[3,2-c]喹诺嗪
描述了一个nis促进的分子内C-N键与3-(1h -吲哚-3-基)-2-(吡啶-2-基)丙酸酯的级联反应,用于合成多环吲哚骨架,吲哚[3,2-c]喹诺嗪和1,9-二氢吡唑[4 ',3 ':5,6]吡啶[2,3-b]吲哚。该工艺具有原料可及、条件温和、操作简单、产率高等优点。吲哚[3,2-c]喹诺嗪具有良好的荧光特性和对活细胞的有效染色,可靶向溶酶体和线粒体。此外,在MTT实验中,产物对肿瘤细胞显示出显著的抗增殖活性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
期刊最新文献
Lewis Base-Catalyzed Three-Component Reaction of Amines, Isocyanates, and Morita–Baylis–Hillman Carbonates: Access to Fully Substituted 5-Methylenedihydrouracils London Dispersion Favors Cis Selectivity in the Johnson–Corey–Chaykovsky Epoxidation Total Synthesis of Antimalarial Macrolide Strasseriolide A by Ni/Zr-Mediated Reductive Ketone Coupling Elemental Sulfur/Base/Water: An Efficient System for the Synthesis of 2-Phosphoryl-Substituted Benzazoles via a Willgerodt-Kindler-Type Reaction Unified Access to Rearranged Steroids via Controlled B-Ring Remodeling of Ergosterol
×
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:604180095
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