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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2020
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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) |
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| 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 |
| work_keys_str_mv |
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