دورية أكاديمية
A Straightforward Method for Synthesizing Bioactive Resorcinolic Lipid Analogues
| العنوان: | A Straightforward Method for Synthesizing Bioactive Resorcinolic Lipid Analogues |
|---|---|
| المؤلفون: | Denilson Silva dos Santos, Alisson Meza, Roberto da Silva Gomes, Dênis Pires de Lima, Adilson Beatriz |
| المصدر: | Orbital: The Electronic Journal of Chemistry, Vol 12, Iss 2 (2020) |
| بيانات النشر: | Universidade Federal de Mato Grosso do Sul, 2020. |
| سنة النشر: | 2020 |
| المجموعة: | LCC:Science LCC:Chemistry |
| مصطلحات موضوعية: | resorcinolic lipids, cytosporones, phomopsin C, cladosporin, Science, Chemistry, QD1-999 |
| الوصف: | Resorcinolic lipids, a class of bioactive amphiphilic molecules found widely in nature, hold potential for a variety of biological and industrial applications. This report describes the synthesis of three bioactive structural analogues of resorcinolic lipids, obtained by subjecting ethyl (E)-2-undecenoate and ethyl acetoacetate to a Michael reaction in the presence of sodium ethoxide to generate a Michael adduct, followed by cyclization in the reaction medium. Ethyl 2-octyl-4,6-dioxocyclohexanecarboxylate (7) was thus produced with a 60% yield. To perform an aromatization step, 7 was subsequently treated with I2 in methanol under reflux, producing a combined 80% yield of 2,4-dimethoxy-6-octyl-ethyl benzoate (1) and 2-hydroxy-4-methoxy-6-octyl-ethyl benzoate (2) at a 7:3 ratio, respectively. 2-Hydroxy-4-methoxy-6-octyl-benzoic acid was obtained with a 60% yield by treating 1 with BBr3/CHCl3. The structures of the synthesized compounds and intermediates were elucidated by 1H and 13C NMR spectroscopy, employing two-dimensional techniques (HSQC and HMBC). DOI: http://dx.doi.org/10.17807/orbital.v12i2.237 |
| نوع الوثيقة: | article |
| وصف الملف: | electronic resource |
| اللغة: | English |
| تدمد: | 1984-6428 |
| Relation: | https://periodicos.ufms.br/index.php/orbital/article/view/15754; https://doaj.org/toc/1984-6428 |
| URL الوصول: | https://doaj.org/article/d5cb1c9994004b8396581b062a713fe4 |
| رقم الأكسشن: | edsdoj.5cb1c9994004b8396581b062a713fe4 |
| قاعدة البيانات: | Directory of Open Access Journals |
Full Text Finder | تدمد: | 19846428 |
|---|