Dmitriy F. Mertsalov, Dmitriy M. Shchevnikov, Lala V. Lovtsevich, Roman A. Novikov, Victor N. Khrustalev, Mikhail S. Grigoriev, Anna A. Romanycheva, Anton A. Shetnev, Olga P. Bychkova, Alexey S. Trenin and Vladimir P. Zaytsev
{"title":"通过分子内 Diels-Alder Furan (IMDAF) 反应制备查耳酮脲取代的 3а,6-环氧异吲哚的捷径。抗菌和抗真菌活性","authors":"Dmitriy F. Mertsalov, Dmitriy M. Shchevnikov, Lala V. Lovtsevich, Roman A. Novikov, Victor N. Khrustalev, Mikhail S. Grigoriev, Anna A. Romanycheva, Anton A. Shetnev, Olga P. Bychkova, Alexey S. Trenin and Vladimir P. Zaytsev","doi":"10.1039/D4NJ01174K","DOIUrl":null,"url":null,"abstract":"<p >\r\n <em>N</em>-Furfuryl allylamines react with a broad range of isocyanates, isothiocyanates, isoselenocyanates with the formation of a 3<em>a</em>,6-epoxyisoindole core in one synthetic stage. The interaction sequence involves two consecutive steps: the nucleophilic addition reaction and the intramolecular Diels–Alder furane (IMDAF) reaction. The scope and limitations of the proposed method were thoroughly investigated, and it was revealed that the key [4+2] cycloaddition step proceeds through an <em>exo</em>-transition state, giving rise to the exclusive formation of a single diastereomer of the target heterocycle. Dynamic temperature NMR analysis allowed to fully investigating a case of coalescence of NMR signals and determined the coalescence temperature during the transition O → Se. The antimicrobial properties of the obtained compounds against sensitive strains of yeast <em>Candida albicans</em>, fungus <em>Aspergillus niger</em> and bacteria including <em>Staphylococcus aureus</em>, <em>Micrococcus luteus</em>, <em>Pseudomonas fluorescens</em> were identified.</p>","PeriodicalId":95,"journal":{"name":"New Journal of Chemistry","volume":null,"pages":null},"PeriodicalIF":2.7000,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"The short route to chalcogenurea-substituted 3a,6-epoxyisoindoles via an intramolecular Diels–Alder furan (IMDAF) reaction. Antibacterial and antifungal activity†\",\"authors\":\"Dmitriy F. Mertsalov, Dmitriy M. Shchevnikov, Lala V. Lovtsevich, Roman A. Novikov, Victor N. Khrustalev, Mikhail S. Grigoriev, Anna A. Romanycheva, Anton A. Shetnev, Olga P. Bychkova, Alexey S. Trenin and Vladimir P. Zaytsev\",\"doi\":\"10.1039/D4NJ01174K\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >\\r\\n <em>N</em>-Furfuryl allylamines react with a broad range of isocyanates, isothiocyanates, isoselenocyanates with the formation of a 3<em>a</em>,6-epoxyisoindole core in one synthetic stage. The interaction sequence involves two consecutive steps: the nucleophilic addition reaction and the intramolecular Diels–Alder furane (IMDAF) reaction. The scope and limitations of the proposed method were thoroughly investigated, and it was revealed that the key [4+2] cycloaddition step proceeds through an <em>exo</em>-transition state, giving rise to the exclusive formation of a single diastereomer of the target heterocycle. Dynamic temperature NMR analysis allowed to fully investigating a case of coalescence of NMR signals and determined the coalescence temperature during the transition O → Se. The antimicrobial properties of the obtained compounds against sensitive strains of yeast <em>Candida albicans</em>, fungus <em>Aspergillus niger</em> and bacteria including <em>Staphylococcus aureus</em>, <em>Micrococcus luteus</em>, <em>Pseudomonas fluorescens</em> were identified.</p>\",\"PeriodicalId\":95,\"journal\":{\"name\":\"New Journal of Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2024-07-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"New Journal of Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2024/nj/d4nj01174k\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"New Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/nj/d4nj01174k","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
摘要
N-糠基烯丙基胺与多种异氰酸酯、异硫氰酸酯和异硒氰酸酯发生反应,在一个合成阶段形成 3a,6-环氧异吲哚核。相互作用顺序包括两个连续步骤:亲核加成反应和分子内 Dielse-Alder 呋喃е(IMDAF)反应。研究人员对所提出方法的范围和局限性进行了深入研究,发现关键的[4 + 2]环加成步骤是通过外蜕变状态进行的,只形成目标杂环的单一非对映异构体。通过动态温度核磁共振分析,可以全面研究核磁共振信号凝聚的情况,并确定 O → Se 转变过程中的凝聚温度。确定了所获化合物对敏感酵母菌白色念珠菌、真菌黑曲霉和细菌(包括金黄色葡萄球菌、黄绿微球菌和荧光假单胞菌)的抗菌特性。
The short route to chalcogenurea-substituted 3a,6-epoxyisoindoles via an intramolecular Diels–Alder furan (IMDAF) reaction. Antibacterial and antifungal activity†
N-Furfuryl allylamines react with a broad range of isocyanates, isothiocyanates, isoselenocyanates with the formation of a 3a,6-epoxyisoindole core in one synthetic stage. The interaction sequence involves two consecutive steps: the nucleophilic addition reaction and the intramolecular Diels–Alder furane (IMDAF) reaction. The scope and limitations of the proposed method were thoroughly investigated, and it was revealed that the key [4+2] cycloaddition step proceeds through an exo-transition state, giving rise to the exclusive formation of a single diastereomer of the target heterocycle. Dynamic temperature NMR analysis allowed to fully investigating a case of coalescence of NMR signals and determined the coalescence temperature during the transition O → Se. The antimicrobial properties of the obtained compounds against sensitive strains of yeast Candida albicans, fungus Aspergillus niger and bacteria including Staphylococcus aureus, Micrococcus luteus, Pseudomonas fluorescens were identified.