Improved synthesis of two quisqualic acid analogs containing hydantoin and imidazolidinone moieties

IF 1.4 4区 化学 Q3 CHEMISTRY, ORGANIC
Aleksandr P. Makhin, Vasily S. Miturich, Matvey V. Vavilov, Maria S. Lyakhovich, Anastasia A. Andrianova, Renata I. Zagitova, Vladimir I. Shmygarev, Anastasia A. Fadeeva, Oleg N. Yatskin, Olga A. Belozerova, Aristides Tsatsakis, Ilia V. Yampolsky, Zinaida M. Kaskova
{"title":"Improved synthesis of two quisqualic acid analogs containing hydantoin and imidazolidinone moieties","authors":"Aleksandr P. Makhin, Vasily S. Miturich, Matvey V. Vavilov, Maria S. Lyakhovich, Anastasia A. Andrianova, Renata I. Zagitova, Vladimir I. Shmygarev, Anastasia A. Fadeeva, Oleg N. Yatskin, Olga A. Belozerova, Aristides Tsatsakis, Ilia V. Yampolsky, Zinaida M. Kaskova","doi":"10.1007/s10593-024-03331-1","DOIUrl":null,"url":null,"abstract":"<p>In the light of recent progress in the development of SARS-CoV-2 main protease inhibitors, the synthesis of their key fragment, heterocyclic amino acids, is of great interest. Here, we report a method for the preparation of two new quisqualic acid analogs containing hydantoin and imidazolidinone moieties. The hydantoin analog was obtained using an amide ester cyclization, while the imidazolidinone unit was constructed by reductive amination and subsequent cyclization of a substituted ethylenediamine with carbonyldiimidazole. The presented approach provides the convergent synthesis of target analogs in 8 and 5 steps respectively.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.4000,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry of Heterocyclic Compounds","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s10593-024-03331-1","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

In the light of recent progress in the development of SARS-CoV-2 main protease inhibitors, the synthesis of their key fragment, heterocyclic amino acids, is of great interest. Here, we report a method for the preparation of two new quisqualic acid analogs containing hydantoin and imidazolidinone moieties. The hydantoin analog was obtained using an amide ester cyclization, while the imidazolidinone unit was constructed by reductive amination and subsequent cyclization of a substituted ethylenediamine with carbonyldiimidazole. The presented approach provides the convergent synthesis of target analogs in 8 and 5 steps respectively.

Abstract Image

含有海因和咪唑烷酮分子的两种奎奎宁酸类似物的改进合成方法
鉴于最近在开发 SARS-CoV-2 主要蛋白酶抑制剂方面取得的进展,其关键片段杂环氨基酸的合成备受关注。在此,我们报告了一种制备含有海因和咪唑烷酮分子的两种新奎喹酸类似物的方法。海因类似物是通过酰胺酯环化反应获得的,而咪唑烷酮单元则是通过还原胺化反应以及随后的取代乙二胺与羰基二咪唑环化反应生成的。所介绍的方法分别只需 8 个和 5 个步骤就能聚合合成目标类似物。
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 求助全文
来源期刊
CiteScore
2.90
自引率
13.30%
发文量
98
审稿时长
1 months
期刊介绍: The international journal Chemistry of Heterocyclic Compounds publishes original papers, short communications, reviews, and mini-reviews dealing with problems in the field of heterocyclic chemistry in Russian and English. The Journal also publishes reviews and annotations on new books and brief reports on conferences in the field of heterocyclic chemistry, as well as commemo­ra­tives dedicated to prominent heterocyclic chemists.
×
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
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
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 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信