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11H-Benzo[4,5]imidazo[1,2-a]indol-11-one as a New Precursor of Azomethine Ylides: 1,3-Dipolar Cycloaddition Reactions with Cyclopropenes and Maleimides

The possibility of generating azomethine ylides from 11H-benzo[4,5]imidazo[1,2-a]indol-11-one and amino acids is shown for the first time. Based on the cycloaddition reactions of these azomethine ylides with cyclopropenes and maleimides, cyclopropa[a]pyrrolizines, 3-azabicyclo[3.1.0]hexanes, and pyr...

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Autores principales: Filatov, Alexander S., Pronina, Yulia A., Selivanov, Stanislav I., Shmakov, Stanislav V., Uspenski, Anton A., Boitsov, Vitali M., Stepakov, Alexander V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9657675/
https://www.ncbi.nlm.nih.gov/pubmed/36361988
http://dx.doi.org/10.3390/ijms232113202
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author Filatov, Alexander S.
Pronina, Yulia A.
Selivanov, Stanislav I.
Shmakov, Stanislav V.
Uspenski, Anton A.
Boitsov, Vitali M.
Stepakov, Alexander V.
author_facet Filatov, Alexander S.
Pronina, Yulia A.
Selivanov, Stanislav I.
Shmakov, Stanislav V.
Uspenski, Anton A.
Boitsov, Vitali M.
Stepakov, Alexander V.
author_sort Filatov, Alexander S.
collection PubMed
description The possibility of generating azomethine ylides from 11H-benzo[4,5]imidazo[1,2-a]indol-11-one and amino acids is shown for the first time. Based on the cycloaddition reactions of these azomethine ylides with cyclopropenes and maleimides, cyclopropa[a]pyrrolizines, 3-azabicyclo[3.1.0]hexanes, and pyrrolo[3,4-a]pyrrolizines spiro-fused with a benzo[4,5]imidazo[1,2-a]indole fragment were synthesized. Spirocyclic compounds were obtained in moderate to good yields, albeit with poor diastereoselectivity. Density functional theory calculations were performed to obtain an insight into the mechanism of the 1,3-dipolar cycloaddition of 11H-benzo[4,5]imidazo[1,2-a]indol-11-one-derived azomethine ylides to cyclopropenes. The cytotoxic activity of some of the obtained cycloadducts against the human erythroleukemia (K562) cell line was evaluated in vitro by MTS-assay.
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spelling pubmed-96576752022-11-15 11H-Benzo[4,5]imidazo[1,2-a]indol-11-one as a New Precursor of Azomethine Ylides: 1,3-Dipolar Cycloaddition Reactions with Cyclopropenes and Maleimides Filatov, Alexander S. Pronina, Yulia A. Selivanov, Stanislav I. Shmakov, Stanislav V. Uspenski, Anton A. Boitsov, Vitali M. Stepakov, Alexander V. Int J Mol Sci Article The possibility of generating azomethine ylides from 11H-benzo[4,5]imidazo[1,2-a]indol-11-one and amino acids is shown for the first time. Based on the cycloaddition reactions of these azomethine ylides with cyclopropenes and maleimides, cyclopropa[a]pyrrolizines, 3-azabicyclo[3.1.0]hexanes, and pyrrolo[3,4-a]pyrrolizines spiro-fused with a benzo[4,5]imidazo[1,2-a]indole fragment were synthesized. Spirocyclic compounds were obtained in moderate to good yields, albeit with poor diastereoselectivity. Density functional theory calculations were performed to obtain an insight into the mechanism of the 1,3-dipolar cycloaddition of 11H-benzo[4,5]imidazo[1,2-a]indol-11-one-derived azomethine ylides to cyclopropenes. The cytotoxic activity of some of the obtained cycloadducts against the human erythroleukemia (K562) cell line was evaluated in vitro by MTS-assay. MDPI 2022-10-30 /pmc/articles/PMC9657675/ /pubmed/36361988 http://dx.doi.org/10.3390/ijms232113202 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Filatov, Alexander S.
Pronina, Yulia A.
Selivanov, Stanislav I.
Shmakov, Stanislav V.
Uspenski, Anton A.
Boitsov, Vitali M.
Stepakov, Alexander V.
11H-Benzo[4,5]imidazo[1,2-a]indol-11-one as a New Precursor of Azomethine Ylides: 1,3-Dipolar Cycloaddition Reactions with Cyclopropenes and Maleimides
title 11H-Benzo[4,5]imidazo[1,2-a]indol-11-one as a New Precursor of Azomethine Ylides: 1,3-Dipolar Cycloaddition Reactions with Cyclopropenes and Maleimides
title_full 11H-Benzo[4,5]imidazo[1,2-a]indol-11-one as a New Precursor of Azomethine Ylides: 1,3-Dipolar Cycloaddition Reactions with Cyclopropenes and Maleimides
title_fullStr 11H-Benzo[4,5]imidazo[1,2-a]indol-11-one as a New Precursor of Azomethine Ylides: 1,3-Dipolar Cycloaddition Reactions with Cyclopropenes and Maleimides
title_full_unstemmed 11H-Benzo[4,5]imidazo[1,2-a]indol-11-one as a New Precursor of Azomethine Ylides: 1,3-Dipolar Cycloaddition Reactions with Cyclopropenes and Maleimides
title_short 11H-Benzo[4,5]imidazo[1,2-a]indol-11-one as a New Precursor of Azomethine Ylides: 1,3-Dipolar Cycloaddition Reactions with Cyclopropenes and Maleimides
title_sort 11h-benzo[4,5]imidazo[1,2-a]indol-11-one as a new precursor of azomethine ylides: 1,3-dipolar cycloaddition reactions with cyclopropenes and maleimides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9657675/
https://www.ncbi.nlm.nih.gov/pubmed/36361988
http://dx.doi.org/10.3390/ijms232113202
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