Cargando…
Synthesis and Anti-Tuberculosis Activity of the Marine Natural Product Caulerpin and Its Analogues
Caulerpin (1a), a bis-indole alkaloid from the marine algal Caulerpa sp., was synthesized in three reaction steps with an overall yield of 11%. The caulerpin analogues (1b–1g) were prepared using the same synthetic pathway with overall yields between 3% and 8%. The key reaction involved a radical ox...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2014
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4012461/ https://www.ncbi.nlm.nih.gov/pubmed/24681629 http://dx.doi.org/10.3390/md12041757 |
_version_ | 1782314935520329728 |
---|---|
author | Canché Chay, Cristina I. Gómez Cansino, Rocío Espitia Pinzón, Clara I. Torres-Ochoa, Rubén O. Martínez, Roberto |
author_facet | Canché Chay, Cristina I. Gómez Cansino, Rocío Espitia Pinzón, Clara I. Torres-Ochoa, Rubén O. Martínez, Roberto |
author_sort | Canché Chay, Cristina I. |
collection | PubMed |
description | Caulerpin (1a), a bis-indole alkaloid from the marine algal Caulerpa sp., was synthesized in three reaction steps with an overall yield of 11%. The caulerpin analogues (1b–1g) were prepared using the same synthetic pathway with overall yields between 3% and 8%. The key reaction involved a radical oxidative aromatic substitution involving xanthate (3) and 3-formylindole compounds (4a–4g). All bis-indole compounds synthesized were evaluated against the Mycobacterium tuberculosis strain H37Rv, and 1a was found to display excellent activity (IC(50) 0.24 µM). |
format | Online Article Text |
id | pubmed-4012461 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-40124612014-05-07 Synthesis and Anti-Tuberculosis Activity of the Marine Natural Product Caulerpin and Its Analogues Canché Chay, Cristina I. Gómez Cansino, Rocío Espitia Pinzón, Clara I. Torres-Ochoa, Rubén O. Martínez, Roberto Mar Drugs Article Caulerpin (1a), a bis-indole alkaloid from the marine algal Caulerpa sp., was synthesized in three reaction steps with an overall yield of 11%. The caulerpin analogues (1b–1g) were prepared using the same synthetic pathway with overall yields between 3% and 8%. The key reaction involved a radical oxidative aromatic substitution involving xanthate (3) and 3-formylindole compounds (4a–4g). All bis-indole compounds synthesized were evaluated against the Mycobacterium tuberculosis strain H37Rv, and 1a was found to display excellent activity (IC(50) 0.24 µM). MDPI 2014-03-27 /pmc/articles/PMC4012461/ /pubmed/24681629 http://dx.doi.org/10.3390/md12041757 Text en © 2014 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Canché Chay, Cristina I. Gómez Cansino, Rocío Espitia Pinzón, Clara I. Torres-Ochoa, Rubén O. Martínez, Roberto Synthesis and Anti-Tuberculosis Activity of the Marine Natural Product Caulerpin and Its Analogues |
title | Synthesis and Anti-Tuberculosis Activity of the Marine Natural Product Caulerpin and Its Analogues |
title_full | Synthesis and Anti-Tuberculosis Activity of the Marine Natural Product Caulerpin and Its Analogues |
title_fullStr | Synthesis and Anti-Tuberculosis Activity of the Marine Natural Product Caulerpin and Its Analogues |
title_full_unstemmed | Synthesis and Anti-Tuberculosis Activity of the Marine Natural Product Caulerpin and Its Analogues |
title_short | Synthesis and Anti-Tuberculosis Activity of the Marine Natural Product Caulerpin and Its Analogues |
title_sort | synthesis and anti-tuberculosis activity of the marine natural product caulerpin and its analogues |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4012461/ https://www.ncbi.nlm.nih.gov/pubmed/24681629 http://dx.doi.org/10.3390/md12041757 |
work_keys_str_mv | AT canchechaycristinai synthesisandantituberculosisactivityofthemarinenaturalproductcaulerpinanditsanalogues AT gomezcansinorocio synthesisandantituberculosisactivityofthemarinenaturalproductcaulerpinanditsanalogues AT espitiapinzonclarai synthesisandantituberculosisactivityofthemarinenaturalproductcaulerpinanditsanalogues AT torresochoarubeno synthesisandantituberculosisactivityofthemarinenaturalproductcaulerpinanditsanalogues AT martinezroberto synthesisandantituberculosisactivityofthemarinenaturalproductcaulerpinanditsanalogues |