6-Azido hyacinthacine A2 gives a straightforward access to the first multivalent pyrrolizidine architectures
| العنوان: | 6-Azido hyacinthacine A2 gives a straightforward access to the first multivalent pyrrolizidine architectures |
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| المؤلفون: | Antonio J. Moreno-Vargas, Giampiero D'Adamio, Andrea Goti, Elena Moreno-Clavijo, Inmaculada Robina, Francesca Cardona, Camilla Parmeggiani |
| المصدر: | Organic & biomolecular chemistry 12 (2014): 6250–6266. doi:10.1039/c4ob01117a info:cnr-pdr/source/autori:D'Adamio, Giampiero; Parmeggiani, Camilla; Goti, Andrea; Moreno-Vargas, Antonio J.; Moreno-Clavijo, Elena; Robina, Inmaculada; Cardona, Francesca/titolo:6-Azido hyacinthacine A(2) gives a straightforward access to the first multivalent pyrrolizidine architectures/doi:10.1039%2Fc4ob01117a/rivista:Organic & biomolecular chemistry/anno:2014/pagina_da:6250/pagina_a:6266/intervallo_pagine:6250–6266/volume:12 |
| سنة النشر: | 2014 |
| مصطلحات موضوعية: | chemistry.chemical_classification, Cycloaddition Reaction, Glycoside Hydrolases, Chemistry, Stereochemistry, Organic Chemistry, Alkyne, 6-azido hyacinthacine A2, Saccharomyces cerevisiae, Biochemistry, Cycloaddition, Nitrone, chemistry.chemical_compound, Pyrrolizidine, multivalent pyrrolizidine iminosugars, Click chemistry, Moiety, Stereoselectivity, Pyrroles, Physical and Theoretical Chemistry, Enzyme Inhibitors, Pyrrolizidine Alkaloids |
| الوصف: | The synthesis of the first multivalent pyrrolizidine iminosugars is reported. The key azido intermediates 4 and 31 were prepared after suitable synthetic elaboration of the cycloadduct obtained from 1,3-dipolar cycloaddition of D-arabinose derived nitrone to dimethylacrylamide. The key step of the strategy was the stereoselective installation of an azido moiety at C-6 of the pyrrolizidine skeleton. The click reaction with different monovalent and dendrimeric alkyne scaffolds allowed the preparation of a library of new mono- and multivalent pyrrolizidine compounds that were preliminarily assayed as glycosidase inhibitors towards a panel of commercially available glycosyl hydrolases. |
| تدمد: | 1477-0539 |
| DOI: | 10.1039/c4ob01117a |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::aeb1eee092c1407ac383fd3a048a1764 https://pubmed.ncbi.nlm.nih.gov/25008992 |
| رقم الانضمام: | edsair.doi.dedup.....aeb1eee092c1407ac383fd3a048a1764 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 14770539 |
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| DOI: | 10.1039/c4ob01117a |