{"title":"合成新型 GABA-三唑拴系的莨菪碱衍生物及其抗癌活性","authors":"Farzaneh Karimi, Peyman Salehi, Morteza Bararjanian","doi":"10.1007/s00706-024-03170-y","DOIUrl":null,"url":null,"abstract":"<p>Synthesis of novel noscapine triazole tethered derivatives with <i>γ</i>-aminobutyric acid (GABA) linker is reported. Attachment of the linker was done by <i>N</i>-demethylation of noscapine followed by coupling with <i>N</i>-Boc protected GABA. The straightforward synthesis of the target molecules was made by a three-component reaction between GABA-noscapine, <i>p</i>-nitrophenyl azide, and commercially available ketones under metal-free conditions to produce a library with diverse functional groups. Anticancer activity of the synthesized derivatives was evaluated on MCF-7 cancer cell line. The best anticancer activity was demonstrated by a compound with an IC<sub>50</sub> value of 57.2 µM, close to that of noscapine (IC<sub>50</sub> = 55.2 µM).</p><h3 data-test=\"abstract-sub-heading\">Graphical abstract</h3>","PeriodicalId":19011,"journal":{"name":"Monatshefte für Chemie / Chemical Monthly","volume":"112 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of novel GABA-Triazole tethered derivatives of Noscapine and their anticancer activities\",\"authors\":\"Farzaneh Karimi, Peyman Salehi, Morteza Bararjanian\",\"doi\":\"10.1007/s00706-024-03170-y\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>Synthesis of novel noscapine triazole tethered derivatives with <i>γ</i>-aminobutyric acid (GABA) linker is reported. Attachment of the linker was done by <i>N</i>-demethylation of noscapine followed by coupling with <i>N</i>-Boc protected GABA. The straightforward synthesis of the target molecules was made by a three-component reaction between GABA-noscapine, <i>p</i>-nitrophenyl azide, and commercially available ketones under metal-free conditions to produce a library with diverse functional groups. Anticancer activity of the synthesized derivatives was evaluated on MCF-7 cancer cell line. The best anticancer activity was demonstrated by a compound with an IC<sub>50</sub> value of 57.2 µM, close to that of noscapine (IC<sub>50</sub> = 55.2 µM).</p><h3 data-test=\\\"abstract-sub-heading\\\">Graphical abstract</h3>\",\"PeriodicalId\":19011,\"journal\":{\"name\":\"Monatshefte für Chemie / Chemical Monthly\",\"volume\":\"112 1\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-02-24\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Monatshefte für Chemie / Chemical Monthly\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1007/s00706-024-03170-y\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Monatshefte für Chemie / Chemical Monthly","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1007/s00706-024-03170-y","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Synthesis of novel GABA-Triazole tethered derivatives of Noscapine and their anticancer activities
Synthesis of novel noscapine triazole tethered derivatives with γ-aminobutyric acid (GABA) linker is reported. Attachment of the linker was done by N-demethylation of noscapine followed by coupling with N-Boc protected GABA. The straightforward synthesis of the target molecules was made by a three-component reaction between GABA-noscapine, p-nitrophenyl azide, and commercially available ketones under metal-free conditions to produce a library with diverse functional groups. Anticancer activity of the synthesized derivatives was evaluated on MCF-7 cancer cell line. The best anticancer activity was demonstrated by a compound with an IC50 value of 57.2 µM, close to that of noscapine (IC50 = 55.2 µM).
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