دورية أكاديمية
Stereoselective Synthesis and Application of Gibberellic Acid-Derived Aminodiols
| العنوان: | Stereoselective Synthesis and Application of Gibberellic Acid-Derived Aminodiols |
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| المؤلفون: | Zein Alabdeen Khdar, Tam Minh Le, Zsuzsanna Schelz, István Zupkó, Zsolt Szakonyi |
| المصدر: | International Journal of Molecular Sciences, Vol 23, Iss 18, p 10366 (2022) |
| بيانات النشر: | MDPI AG, 2022. |
| سنة النشر: | 2022 |
| المجموعة: | LCC:Biology (General) LCC:Chemistry |
| مصطلحات موضوعية: | gibberellic acid, allo-gibberic acid, 3-amino-1,2-diols, antiproliferative activity, diterpene, Biology (General), QH301-705.5, Chemistry, QD1-999 |
| الوصف: | A series of gibberellic acid-based aminodiols was designed and synthesized from commercially available gibberellic acid. Exposure of gibberellic acid to hydrochloric acid under reflux conditions resulted in aromatization followed by rearrangement to form allo-gibberic acid. The key intermediate, ethyl allo-gibberate, was prepared according to literature methods. Epoxidation of key intermediate and subsequent ring-opening of the corresponding epoxide with different nucleophiles resulted in N-substituted aminodiols. The regioselective ring closure of N-benzyl-substituted aminodiol with formaldehyde was also investigated. All aminodiol derivatives were well characterized using modern spectroscopic techniques and evaluated for their antiproliferative activity against a panel of human cancer cell lines. In addition, structure–activity relationships were examined by assessing substituent effects on the aminodiol systems. The results indicated that aminodiols containing aromatic rings on their nitrogen substituents displayed significant cytotoxic effects. Among these agents, N-naphthylmethyl-substituted aminodiols were found to be the most potent candidates in this series. One of these molecules exhibited a modest cancer selectivity determined by non-cancerous fibroblast cells. A docking study was also made to exploit the observed results. |
| نوع الوثيقة: | article |
| وصف الملف: | electronic resource |
| اللغة: | English |
| تدمد: | 23181036 1422-0067 1661-6596 |
| Relation: | https://www.mdpi.com/1422-0067/23/18/10366; https://doaj.org/toc/1661-6596; https://doaj.org/toc/1422-0067 |
| DOI: | 10.3390/ijms231810366 |
| URL الوصول: | https://doaj.org/article/68852f3bbac44adcbd302b36cd550187 |
| رقم الأكسشن: | edsdoj.68852f3bbac44adcbd302b36cd550187 |
| قاعدة البيانات: | Directory of Open Access Journals |
Full Text Finder | تدمد: | 23181036 14220067 16616596 |
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| DOI: | 10.3390/ijms231810366 |