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Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines

An efficient approach towards the synthesis of 6-aryl-4-azidocinnolines was developed with the aim of exploring the photophysical properties of 6-aryl-4-azidocinnolines and their click reaction products with alkynes, 6-aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines. The synthetic route is based on the Ric...

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Autores principales: Danilkina, Natalia A., Bukhtiiarova, Nina S., Govdi, Anastasia I., Vasileva, Anna A., Rumyantsev, Andrey M., Volkov, Artemii A., Sharaev, Nikita I., Povolotskiy, Alexey V., Boyarskaya, Irina A., Kornyakov, Ilya V., Tokareva, Polina V., Balova, Irina A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6651781/
https://www.ncbi.nlm.nih.gov/pubmed/31252657
http://dx.doi.org/10.3390/molecules24132386
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author Danilkina, Natalia A.
Bukhtiiarova, Nina S.
Govdi, Anastasia I.
Vasileva, Anna A.
Rumyantsev, Andrey M.
Volkov, Artemii A.
Sharaev, Nikita I.
Povolotskiy, Alexey V.
Boyarskaya, Irina A.
Kornyakov, Ilya V.
Tokareva, Polina V.
Balova, Irina A.
author_facet Danilkina, Natalia A.
Bukhtiiarova, Nina S.
Govdi, Anastasia I.
Vasileva, Anna A.
Rumyantsev, Andrey M.
Volkov, Artemii A.
Sharaev, Nikita I.
Povolotskiy, Alexey V.
Boyarskaya, Irina A.
Kornyakov, Ilya V.
Tokareva, Polina V.
Balova, Irina A.
author_sort Danilkina, Natalia A.
collection PubMed
description An efficient approach towards the synthesis of 6-aryl-4-azidocinnolines was developed with the aim of exploring the photophysical properties of 6-aryl-4-azidocinnolines and their click reaction products with alkynes, 6-aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines. The synthetic route is based on the Richter-type cyclization of 2-ethynyl-4-aryltriazenes with the formation of 4-bromo-6-arylcinnolines and nucleophilic substitution of a bromine atom with an azide functional group. The developed synthetic approach is tolerant to variations of functional groups on the aryl moiety. The resulting azidocinnolines were found to be reactive in both CuAAC with terminal alkynes and SPAAC with diazacyclononyne, yielding 4-triazolylcinnolines. It was found that 4-azido-6-arylcinnolines possess weak fluorescent properties, while conversion of the azido function into a triazole ring led to complete fluorescence quenching. The lack of fluorescence in triazoles could be explained by the non-planar structure of triazolylcinnolines and a possible photoinduced electron transfer (PET) mechanism. Among the series of 4-triazolylcinnoline derivatives a compound bearing hydroxyalkyl substituent at triazole ring was found to be cytotoxic to HeLa cells.
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spelling pubmed-66517812019-08-08 Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines Danilkina, Natalia A. Bukhtiiarova, Nina S. Govdi, Anastasia I. Vasileva, Anna A. Rumyantsev, Andrey M. Volkov, Artemii A. Sharaev, Nikita I. Povolotskiy, Alexey V. Boyarskaya, Irina A. Kornyakov, Ilya V. Tokareva, Polina V. Balova, Irina A. Molecules Article An efficient approach towards the synthesis of 6-aryl-4-azidocinnolines was developed with the aim of exploring the photophysical properties of 6-aryl-4-azidocinnolines and their click reaction products with alkynes, 6-aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines. The synthetic route is based on the Richter-type cyclization of 2-ethynyl-4-aryltriazenes with the formation of 4-bromo-6-arylcinnolines and nucleophilic substitution of a bromine atom with an azide functional group. The developed synthetic approach is tolerant to variations of functional groups on the aryl moiety. The resulting azidocinnolines were found to be reactive in both CuAAC with terminal alkynes and SPAAC with diazacyclononyne, yielding 4-triazolylcinnolines. It was found that 4-azido-6-arylcinnolines possess weak fluorescent properties, while conversion of the azido function into a triazole ring led to complete fluorescence quenching. The lack of fluorescence in triazoles could be explained by the non-planar structure of triazolylcinnolines and a possible photoinduced electron transfer (PET) mechanism. Among the series of 4-triazolylcinnoline derivatives a compound bearing hydroxyalkyl substituent at triazole ring was found to be cytotoxic to HeLa cells. MDPI 2019-06-27 /pmc/articles/PMC6651781/ /pubmed/31252657 http://dx.doi.org/10.3390/molecules24132386 Text en © 2019 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
Danilkina, Natalia A.
Bukhtiiarova, Nina S.
Govdi, Anastasia I.
Vasileva, Anna A.
Rumyantsev, Andrey M.
Volkov, Artemii A.
Sharaev, Nikita I.
Povolotskiy, Alexey V.
Boyarskaya, Irina A.
Kornyakov, Ilya V.
Tokareva, Polina V.
Balova, Irina A.
Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines
title Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines
title_full Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines
title_fullStr Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines
title_full_unstemmed Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines
title_short Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines
title_sort synthesis and properties of 6-aryl-4-azidocinnolines and 6-aryl-4-(1,2,3-1h-triazol-1-yl)cinnolines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6651781/
https://www.ncbi.nlm.nih.gov/pubmed/31252657
http://dx.doi.org/10.3390/molecules24132386
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