A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives

An oxidative ring opening reaction of the central ring C in the alkaloid Luotonin A and two of its derivatives was found to occur upon heating with an excess amine and potassium carbonate in dimethylsulfoxide (DMSO) solution in the presence of air oxygen. The structure of the novel amide-type produc...

Descripción completa

Detalles Bibliográficos
Autores principales: Ibric, Amra, Dutter, Kathrin, Marian, Brigitte, Haider, Norbert
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151605/
https://www.ncbi.nlm.nih.gov/pubmed/28895937
http://dx.doi.org/10.3390/molecules22091540
_version_ 1783357188977197056
author Ibric, Amra
Dutter, Kathrin
Marian, Brigitte
Haider, Norbert
author_facet Ibric, Amra
Dutter, Kathrin
Marian, Brigitte
Haider, Norbert
author_sort Ibric, Amra
collection PubMed
description An oxidative ring opening reaction of the central ring C in the alkaloid Luotonin A and two of its derivatives was found to occur upon heating with an excess amine and potassium carbonate in dimethylsulfoxide (DMSO) solution in the presence of air oxygen. The structure of the novel amide-type products was elucidated and a possible mechanism for this reaction is proposed. Four of the new compounds show moderate in vitro anticancer activity towards human colon adenocarcinoma cells.
format Online
Article
Text
id pubmed-6151605
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-61516052018-11-13 A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives Ibric, Amra Dutter, Kathrin Marian, Brigitte Haider, Norbert Molecules Article An oxidative ring opening reaction of the central ring C in the alkaloid Luotonin A and two of its derivatives was found to occur upon heating with an excess amine and potassium carbonate in dimethylsulfoxide (DMSO) solution in the presence of air oxygen. The structure of the novel amide-type products was elucidated and a possible mechanism for this reaction is proposed. Four of the new compounds show moderate in vitro anticancer activity towards human colon adenocarcinoma cells. MDPI 2017-09-12 /pmc/articles/PMC6151605/ /pubmed/28895937 http://dx.doi.org/10.3390/molecules22091540 Text en © 2017 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 (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Ibric, Amra
Dutter, Kathrin
Marian, Brigitte
Haider, Norbert
A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives
title A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives
title_full A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives
title_fullStr A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives
title_full_unstemmed A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives
title_short A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives
title_sort facile oxidative opening of the c-ring in luotonin a and derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151605/
https://www.ncbi.nlm.nih.gov/pubmed/28895937
http://dx.doi.org/10.3390/molecules22091540
work_keys_str_mv AT ibricamra afacileoxidativeopeningofthecringinluotoninaandderivatives
AT dutterkathrin afacileoxidativeopeningofthecringinluotoninaandderivatives
AT marianbrigitte afacileoxidativeopeningofthecringinluotoninaandderivatives
AT haidernorbert afacileoxidativeopeningofthecringinluotoninaandderivatives
AT ibricamra facileoxidativeopeningofthecringinluotoninaandderivatives
AT dutterkathrin facileoxidativeopeningofthecringinluotoninaandderivatives
AT marianbrigitte facileoxidativeopeningofthecringinluotoninaandderivatives
AT haidernorbert facileoxidativeopeningofthecringinluotoninaandderivatives

Ejemplares similares