دورية أكاديمية
Synthesis and Transformation of (-)-Isopulegol-Based Chiral β-Aminolactones and β-Aminoamides
| العنوان: | Synthesis and Transformation of (-)-Isopulegol-Based Chiral β-Aminolactones and β-Aminoamides |
|---|---|
| المؤلفون: | Tam Minh Le, Péter Bérdi, István Zupkó, Ferenc Fülöp, Zsolt Szakonyi |
| المصدر: | International Journal of Molecular Sciences, Vol 19, Iss 11, p 3522 (2018) |
| بيانات النشر: | MDPI AG, 2018. |
| سنة النشر: | 2018 |
| المجموعة: | LCC:Biology (General) LCC:Chemistry |
| مصطلحات موضوعية: | terpenoid, β-aminolactones, β-aminoamides, dipeptide, antiproliferative activity, Biology (General), QH301-705.5, Chemistry, QD1-999 |
| الوصف: | A library of isopulegol-based β-amino acid derivatives has been developed from commercially-available (-)-isopulegol. Michael addition of primary and secondary amines towards α,β-unsaturated γ-lactones was accomplished resulting in β-aminolactones in highly-stereoselective reactions. Ring-opening of β-aminolactones with different amines furnished excellent yields of β-aminoamides. Moreover, the applicability of aminolactones in peptide synthesis was examined by opening the lactone ring with α- and β-aminoesters, providing dipeptides as promising chiral substrates for the synthesis of foldamers. The antiproliferative activities of β-aminolactones and β-aminoamides were explored, and the structure-activity relationships were studied from the aspects of the stereochemistry of the monoterpene ring and the substituent effects on the β-aminoamide ring system. The N-unsubstituted (-)-isopulegol-based β-aminoamides exhibited considerable antiproliferative activity against a panel of human adherent cancer cell lines (HeLa, MCF7 and MDA-MB-231). |
| نوع الوثيقة: | article |
| وصف الملف: | electronic resource |
| اللغة: | English |
| تدمد: | 1422-0067 |
| Relation: | https://www.mdpi.com/1422-0067/19/11/3522; https://doaj.org/toc/1422-0067 |
| DOI: | 10.3390/ijms19113522 |
| URL الوصول: | https://doaj.org/article/e785feb3e8f84152ada3d717acc88505 |
| رقم الأكسشن: | edsdoj.785feb3e8f84152ada3d717acc88505 |
| قاعدة البيانات: | Directory of Open Access Journals |
Full Text Finder | تدمد: | 14220067 |
|---|---|
| DOI: | 10.3390/ijms19113522 |