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Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity

We discovered a reaction of nitroalkanes with 2-hydrazinylquinolines, 2-hydrazinylpyridines and bis-2,4-dihydrazinylpyrimidines in polyphosphoric acid (PPA) affording 1,2,4-triazolo[4,3-a]quinolines, 1,2,4-triazolo[4,3-a]pyridines and bis[1,2,4]triazolo[4,3-a:4',3'-c]pyrimidines, respectiv...

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Главные авторы: Aksenov, N. A., Аксенов, Н. А., Aksenov, A. V., Аксенов, А. В., Kirilov, N. K., Кирилов, Н. К., Arutiunov, N. A., Арутюнов, Н. А., Aksenov, D. A., Аксенов, Д. А., Rubin, M. A., Рубин, М. А.
Формат: Статья
Язык:English
Опубликовано: NLM (Medline) 2020
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Online-ссылка:https://dspace.ncfu.ru/handle/20.500.12258/13876
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spelling ir-20.500.12258-138762025-02-12T13:38:52Z Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity Aksenov, N. A. Аксенов, Н. А. Aksenov, A. V. Аксенов, А. В. Kirilov, N. K. Кирилов, Н. К. Arutiunov, N. A. Арутюнов, Н. А. Aksenov, D. A. Аксенов, Д. А. Rubin, M. A. Рубин, М. А. Neuroblastoma Nitroalkanes Synthesis of triazole-fused heterocycles Neuroblastoma therapy We discovered a reaction of nitroalkanes with 2-hydrazinylquinolines, 2-hydrazinylpyridines and bis-2,4-dihydrazinylpyrimidines in polyphosphoric acid (PPA) affording 1,2,4-triazolo[4,3-a]quinolines, 1,2,4-triazolo[4,3-a]pyridines and bis[1,2,4]triazolo[4,3-a:4',3'-c]pyrimidines, respectively. The reaction expands the scope of heterocyclic annulations involving phosphorylated nitronates, believed to be the electrophilic intermediates formed from nitroalkanes in PPA. Several of the synthesized triazoles showed promising anticancer activity by inducing differentiation in neuroblastoma cancer cells. Due to the urgent need for novel differentiation agents for neuroblastoma therapy, this finding warrants further evaluation of this class of compounds against neuroblastoma 2020-09-14T09:50:54Z 2020-09-14T09:50:54Z 2020 Статья Aksenov, N.A., Aksenov, A.V., Kirilov, N.K., Arutiunov, N.A., Aksenov, D.A., Maslivetc, V., Zhao, Z., Du, L., Rubin, M., Kornienko, A. Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity // Organic & biomolecular chemistry. - 2020. - Volume 18. - Issue 34. - Pages 6651-6664 http://hdl.handle.net/20.500.12258/13876 en Organic and Biomolecular Chemistry application/pdf application/pdf NLM (Medline)
institution СКФУ
collection Репозиторий
language English
topic Neuroblastoma
Nitroalkanes
Synthesis of triazole-fused heterocycles
Neuroblastoma therapy
spellingShingle Neuroblastoma
Nitroalkanes
Synthesis of triazole-fused heterocycles
Neuroblastoma therapy
Aksenov, N. A.
Аксенов, Н. А.
Aksenov, A. V.
Аксенов, А. В.
Kirilov, N. K.
Кирилов, Н. К.
Arutiunov, N. A.
Арутюнов, Н. А.
Aksenov, D. A.
Аксенов, Д. А.
Rubin, M. A.
Рубин, М. А.
Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity
description We discovered a reaction of nitroalkanes with 2-hydrazinylquinolines, 2-hydrazinylpyridines and bis-2,4-dihydrazinylpyrimidines in polyphosphoric acid (PPA) affording 1,2,4-triazolo[4,3-a]quinolines, 1,2,4-triazolo[4,3-a]pyridines and bis[1,2,4]triazolo[4,3-a:4',3'-c]pyrimidines, respectively. The reaction expands the scope of heterocyclic annulations involving phosphorylated nitronates, believed to be the electrophilic intermediates formed from nitroalkanes in PPA. Several of the synthesized triazoles showed promising anticancer activity by inducing differentiation in neuroblastoma cancer cells. Due to the urgent need for novel differentiation agents for neuroblastoma therapy, this finding warrants further evaluation of this class of compounds against neuroblastoma
format Статья
author Aksenov, N. A.
Аксенов, Н. А.
Aksenov, A. V.
Аксенов, А. В.
Kirilov, N. K.
Кирилов, Н. К.
Arutiunov, N. A.
Арутюнов, Н. А.
Aksenov, D. A.
Аксенов, Д. А.
Rubin, M. A.
Рубин, М. А.
author_facet Aksenov, N. A.
Аксенов, Н. А.
Aksenov, A. V.
Аксенов, А. В.
Kirilov, N. K.
Кирилов, Н. К.
Arutiunov, N. A.
Арутюнов, Н. А.
Aksenov, D. A.
Аксенов, Д. А.
Rubin, M. A.
Рубин, М. А.
author_sort Aksenov, N. A.
title Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity
title_short Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity
title_full Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity
title_fullStr Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity
title_full_unstemmed Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity
title_sort nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity
publisher NLM (Medline)
publishDate 2020
url https://dspace.ncfu.ru/handle/20.500.12258/13876
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