Mechanistic Study of the Spiroindolones: A New Class of Antimalarials

During the synthesis of the new antimalarial drug candidate NITD609, a high degree of diastereoselectivity was observed in the Pictet-Spengler reaction. By isolating both the 4E and 4Z imine intermediates, a systematic mechanistic study of the reaction under both kinetic and thermodynamic conditions...

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Detalles Bibliográficos
Autores principales: Zou, Bin, Yap, Peiling, Sonntag, Louis-Sebastian, Leong, Seh Yong, Yeung, Bryan K. S., Keller, Thomas H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268731/
https://www.ncbi.nlm.nih.gov/pubmed/22922283
http://dx.doi.org/10.3390/molecules170910131
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author Zou, Bin
Yap, Peiling
Sonntag, Louis-Sebastian
Leong, Seh Yong
Yeung, Bryan K. S.
Keller, Thomas H.
author_facet Zou, Bin
Yap, Peiling
Sonntag, Louis-Sebastian
Leong, Seh Yong
Yeung, Bryan K. S.
Keller, Thomas H.
author_sort Zou, Bin
collection PubMed
description During the synthesis of the new antimalarial drug candidate NITD609, a high degree of diastereoselectivity was observed in the Pictet-Spengler reaction. By isolating both the 4E and 4Z imine intermediates, a systematic mechanistic study of the reaction under both kinetic and thermodynamic conditions was conducted. This study provides insight into the source of the diastereoselectivity for this important class of compounds.
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spelling pubmed-62687312018-12-12 Mechanistic Study of the Spiroindolones: A New Class of Antimalarials Zou, Bin Yap, Peiling Sonntag, Louis-Sebastian Leong, Seh Yong Yeung, Bryan K. S. Keller, Thomas H. Molecules Article During the synthesis of the new antimalarial drug candidate NITD609, a high degree of diastereoselectivity was observed in the Pictet-Spengler reaction. By isolating both the 4E and 4Z imine intermediates, a systematic mechanistic study of the reaction under both kinetic and thermodynamic conditions was conducted. This study provides insight into the source of the diastereoselectivity for this important class of compounds. MDPI 2012-08-24 /pmc/articles/PMC6268731/ /pubmed/22922283 http://dx.doi.org/10.3390/molecules170910131 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ 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
Zou, Bin
Yap, Peiling
Sonntag, Louis-Sebastian
Leong, Seh Yong
Yeung, Bryan K. S.
Keller, Thomas H.
Mechanistic Study of the Spiroindolones: A New Class of Antimalarials
title Mechanistic Study of the Spiroindolones: A New Class of Antimalarials
title_full Mechanistic Study of the Spiroindolones: A New Class of Antimalarials
title_fullStr Mechanistic Study of the Spiroindolones: A New Class of Antimalarials
title_full_unstemmed Mechanistic Study of the Spiroindolones: A New Class of Antimalarials
title_short Mechanistic Study of the Spiroindolones: A New Class of Antimalarials
title_sort mechanistic study of the spiroindolones: a new class of antimalarials
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268731/
https://www.ncbi.nlm.nih.gov/pubmed/22922283
http://dx.doi.org/10.3390/molecules170910131
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