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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...

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Autores principales: Canché Chay, Cristina I., Gómez Cansino, Rocío, Espitia Pinzón, Clara I., Torres-Ochoa, Rubén O., Martínez, Roberto
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
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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).
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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
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