Areej M Jaber, Jalal A Zahra, Mustafa M El-Abadelah, Salim S Sabri, Dua'a S Sabbah
{"title":"Thermodynamic control synthesis of spiro[oxindole-3,3'-pyrrolines] <i>via</i> 1,4-dipolar cycloaddition utilizing imidazo[1,5-<i>a</i>]quinoline.","authors":"Areej M Jaber, Jalal A Zahra, Mustafa M El-Abadelah, Salim S Sabri, Dua'a S Sabbah","doi":"10.1515/znc-2022-0085","DOIUrl":null,"url":null,"abstract":"<p><p>A series of novel 2-(quinolin-2-yl)-spiro[oxindole-3,3'-pyrrolines] were synthesized by one-pot three-component reaction involving dimethyl acetylenedicarboxylate, 1-phenylimidazo[1,5-<i>a</i>]quinoline and <i>N</i>-alkylisatins in chloroform at ∼60 °C for 24 h. Structures of these new spiro derivatives were deduced from HRMS and NMR spectral data. A plausible mechanism for the observed thermodynamic control pathway is presented herewith. Interestingly, the spiro adduct, derived from 5-chloro-1-methylisatin, exhibited excellent antiproliferative activity on MCF7, A549 and Hela human cell lines (IC<sub>50</sub> ≃ 7 μM).</p>","PeriodicalId":49344,"journal":{"name":"Zeitschrift Fur Naturforschung Section C-A Journal of Biosciences","volume":"78 3-4","pages":"141-148"},"PeriodicalIF":2.1000,"publicationDate":"2023-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Zeitschrift Fur Naturforschung Section C-A Journal of Biosciences","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1515/znc-2022-0085","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 1
Abstract
A series of novel 2-(quinolin-2-yl)-spiro[oxindole-3,3'-pyrrolines] were synthesized by one-pot three-component reaction involving dimethyl acetylenedicarboxylate, 1-phenylimidazo[1,5-a]quinoline and N-alkylisatins in chloroform at ∼60 °C for 24 h. Structures of these new spiro derivatives were deduced from HRMS and NMR spectral data. A plausible mechanism for the observed thermodynamic control pathway is presented herewith. Interestingly, the spiro adduct, derived from 5-chloro-1-methylisatin, exhibited excellent antiproliferative activity on MCF7, A549 and Hela human cell lines (IC50 ≃ 7 μM).
期刊介绍：
A Journal of Biosciences: Zeitschrift für Naturforschung C (ZNC) is an international scientific journal and a community resource for the emerging field of natural and natural-like products. The journal publishes original research on the isolation (including structure elucidation), bio-chemical synthesis and bioactivities of natural products, their biochemistry, pharmacology, biotechnology, and their biological activity and innovative developed computational methods for predicting the structure and/or function of natural products. A Journal of Biosciences: Zeitschrift für Naturforschung C (ZNC) welcomes research papers in fields on the chemistry-biology boundary which address scientific ideas and approaches to generate and understand natural compounds on a molecular level and/or use them to stimulate and manipulate biological processes.
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