A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities

A second generation polyphosphoric acid-mediated one-pot three-component synthesis of indoloquinoline scaffold is developed. This improved version of the process involves electrophilically activated nitroalkanes for the installation of strategic C–C and C–N bonds and ring C assembly. This modificati...

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Autores principales: Aksenov, Nicolai A., Aksenov, Alexander V., Kornienko, Alexander, De Carvalho, Annelise, Mathieu, Véronique, Aksenov, Dmitrii A., Ovcharov, Sergei N., Griaznov, Georgii D., Rubin, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9089289/
https://www.ncbi.nlm.nih.gov/pubmed/35558925
http://dx.doi.org/10.1039/c8ra08155g
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author Aksenov, Nicolai A.
Aksenov, Alexander V.
Kornienko, Alexander
De Carvalho, Annelise
Mathieu, Véronique
Aksenov, Dmitrii A.
Ovcharov, Sergei N.
Griaznov, Georgii D.
Rubin, Michael
author_facet Aksenov, Nicolai A.
Aksenov, Alexander V.
Kornienko, Alexander
De Carvalho, Annelise
Mathieu, Véronique
Aksenov, Dmitrii A.
Ovcharov, Sergei N.
Griaznov, Georgii D.
Rubin, Michael
author_sort Aksenov, Nicolai A.
collection PubMed
description A second generation polyphosphoric acid-mediated one-pot three-component synthesis of indoloquinoline scaffold is developed. This improved version of the process involves electrophilically activated nitroalkanes for the installation of strategic C–C and C–N bonds and ring C assembly. This modification allows the elimination of unnecessary solvent change operations and all steps are carried out in a true, uninterrupted one-pot manner. A further improvement involves the possibility to install an ortho-amino group in situ. A synthetic application of this method is showcased by the concise synthesis of an isocryptolepine alkaloid and its synthetic analogs with potent anticancer activities.
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spelling pubmed-90892892022-05-11 A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities Aksenov, Nicolai A. Aksenov, Alexander V. Kornienko, Alexander De Carvalho, Annelise Mathieu, Véronique Aksenov, Dmitrii A. Ovcharov, Sergei N. Griaznov, Georgii D. Rubin, Michael RSC Adv Chemistry A second generation polyphosphoric acid-mediated one-pot three-component synthesis of indoloquinoline scaffold is developed. This improved version of the process involves electrophilically activated nitroalkanes for the installation of strategic C–C and C–N bonds and ring C assembly. This modification allows the elimination of unnecessary solvent change operations and all steps are carried out in a true, uninterrupted one-pot manner. A further improvement involves the possibility to install an ortho-amino group in situ. A synthetic application of this method is showcased by the concise synthesis of an isocryptolepine alkaloid and its synthetic analogs with potent anticancer activities. The Royal Society of Chemistry 2018-11-01 /pmc/articles/PMC9089289/ /pubmed/35558925 http://dx.doi.org/10.1039/c8ra08155g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Aksenov, Nicolai A.
Aksenov, Alexander V.
Kornienko, Alexander
De Carvalho, Annelise
Mathieu, Véronique
Aksenov, Dmitrii A.
Ovcharov, Sergei N.
Griaznov, Georgii D.
Rubin, Michael
A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities
title A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities
title_full A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities
title_fullStr A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities
title_full_unstemmed A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities
title_short A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities
title_sort nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9089289/
https://www.ncbi.nlm.nih.gov/pubmed/35558925
http://dx.doi.org/10.1039/c8ra08155g
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