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Synthesis and antifungal properties of papulacandin derivatives
Derivatives of an antifungal agent that targets the β-(1,3)-D-glucan synthase, papulacandin D, were synthesized and tested for activity. The papulacandin D structure contains a challenging benzannulated spiroketal unit, which is introduced in a palladium-catalyzed cross-coupling reaction of a glycal...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3388860/ https://www.ncbi.nlm.nih.gov/pubmed/23015820 http://dx.doi.org/10.3762/bjoc.8.82 |
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author | van der Kaaden, Marjolein Breukink, Eefjan Pieters, Roland J |
author_facet | van der Kaaden, Marjolein Breukink, Eefjan Pieters, Roland J |
author_sort | van der Kaaden, Marjolein |
collection | PubMed |
description | Derivatives of an antifungal agent that targets the β-(1,3)-D-glucan synthase, papulacandin D, were synthesized and tested for activity. The papulacandin D structure contains a challenging benzannulated spiroketal unit, which is introduced in a palladium-catalyzed cross-coupling reaction of a glycal silanolate and an aryl iodide followed by an oxidative spiroketalization. Four different variants were made, differing in the nature of the acyl side chain with respect to the length, and in the number and stereochemistry of the double bonds. Moderate biological activity was observed for the derivatives with a side chain based on palmitic acid and linoleic acid. |
format | Online Article Text |
id | pubmed-3388860 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-33888602012-09-26 Synthesis and antifungal properties of papulacandin derivatives van der Kaaden, Marjolein Breukink, Eefjan Pieters, Roland J Beilstein J Org Chem Full Research Paper Derivatives of an antifungal agent that targets the β-(1,3)-D-glucan synthase, papulacandin D, were synthesized and tested for activity. The papulacandin D structure contains a challenging benzannulated spiroketal unit, which is introduced in a palladium-catalyzed cross-coupling reaction of a glycal silanolate and an aryl iodide followed by an oxidative spiroketalization. Four different variants were made, differing in the nature of the acyl side chain with respect to the length, and in the number and stereochemistry of the double bonds. Moderate biological activity was observed for the derivatives with a side chain based on palmitic acid and linoleic acid. Beilstein-Institut 2012-05-14 /pmc/articles/PMC3388860/ /pubmed/23015820 http://dx.doi.org/10.3762/bjoc.8.82 Text en Copyright © 2012, van der Kaaden et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper van der Kaaden, Marjolein Breukink, Eefjan Pieters, Roland J Synthesis and antifungal properties of papulacandin derivatives |
title | Synthesis and antifungal properties of papulacandin derivatives |
title_full | Synthesis and antifungal properties of papulacandin derivatives |
title_fullStr | Synthesis and antifungal properties of papulacandin derivatives |
title_full_unstemmed | Synthesis and antifungal properties of papulacandin derivatives |
title_short | Synthesis and antifungal properties of papulacandin derivatives |
title_sort | synthesis and antifungal properties of papulacandin derivatives |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3388860/ https://www.ncbi.nlm.nih.gov/pubmed/23015820 http://dx.doi.org/10.3762/bjoc.8.82 |
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