Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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. / Филатов, А.С.; Пронина, Юлия ; Селиванов, Станислав Иванович; Шмаков, С.В.; Успенский, Антон; Бойцов, Виталий Михайлович; Степаков, Александр Владимирович.
в: International Journal of Molecular Sciences, Том 23, № 21, 13202, 11.2022.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - 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
AU - Филатов, А.С.
AU - Пронина, Юлия
AU - Селиванов, Станислав Иванович
AU - Шмаков, С.В.
AU - Успенский, Антон
AU - Бойцов, Виталий Михайлович
AU - Степаков, Александр Владимирович
N1 - Publisher Copyright: © 2022 by the authors.
PY - 2022/11
Y1 - 2022/11
N2 - The possibility of generating azomethine ylides from 11 H-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.
AB - The possibility of generating azomethine ylides from 11 H-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.
KW - Cycloaddition Reaction
KW - Humans
KW - Maleimides/chemistry
KW - Stereoisomerism
KW - azomethine ylides
KW - cyclopropenes
KW - 11H-benzo[4,5]imidazo[1,2-a]indol-11-one
KW - diastereoselectivity
KW - DFT calculations
KW - 1,3-dipolar cycloaddition
KW - in vitro antiproliferative activity
KW - maleimides
UR - https://www.mendeley.com/catalogue/6ba38a29-ce17-32bb-a525-20dda810e330/
UR - http://www.scopus.com/inward/record.url?scp=85141565704&partnerID=8YFLogxK
U2 - 10.3390/ijms232113202
DO - 10.3390/ijms232113202
M3 - Article
C2 - 36361988
VL - 23
JO - International Journal of Molecular Sciences
JF - International Journal of Molecular Sciences
SN - 1422-0067
IS - 21
M1 - 13202
ER -
ID: 100065801