Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Construction of Spiro[3-azabicyclo[3.1.0]hexanes] via 1,3-Dipolar Cycloaddition of 1,2-Diphenylcyclopropenes to Ninhydrin-Derived Azomethine Ylides. / Ван, Сыци; Филатов, Александр Сергеевич; Lozovskiy, Stanislav V.; Shmakov, Stanislav V; Хорошилова, Олеся Валерьевна; Ларина, Анна Геннадьевна; Селиванов, Станислав Иванович; Бойцов, Виталий Михайлович; Степаков, Александр Владимирович.
в: Synthesis (Germany), Том 53, № 12, 16.06.2021, стр. 2114-2132.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Construction of Spiro[3-azabicyclo[3.1.0]hexanes] via 1,3-Dipolar Cycloaddition of 1,2-Diphenylcyclopropenes to Ninhydrin-Derived Azomethine Ylides
AU - Ван, Сыци
AU - Филатов, Александр Сергеевич
AU - Lozovskiy, Stanislav V.
AU - Shmakov, Stanislav V
AU - Хорошилова, Олеся Валерьевна
AU - Ларина, Анна Геннадьевна
AU - Селиванов, Станислав Иванович
AU - Бойцов, Виталий Михайлович
AU - Степаков, Александр Владимирович
N1 - Publisher Copyright: © 2021. Thieme. All rights reserved. Synthesis 2021, 53, 2114-2132 Georg Thieme Verlag KG, Rudigerstraße 14, 70469 Stuttgart, Germany.
PY - 2021/6/16
Y1 - 2021/6/16
N2 - The multi-component 1,3-dipolar cycloaddition of ninhydrin, α-amino acids (or peptides), and cyclopropenes for the synthesis of spirocyclic heterocycles containing both 3-azabicyclo[3.1.0]hexane and 2 H -indene-1,3-dione motifs has been developed. This method provides easy access to 3-azabicyclo[3.1.0]hexane-2,2′-indenes with complete stereoselectivity and a high degree of atom economy under mild reaction conditions. A broad range of cyclopropenes and α-amino acids have been found to be compatible with the present protocol, which offers an opportunity to create a new library of biologically significant scaffold (3-azabicyclo[3.1.0]hexane). In addition, the сomprehensive study of mechanism of azomethine ylide formation from ninhydrin and sarcosine was performed by means of M11 density functional theory (DFT) calculations. It has been revealed that experimentally observed 1-methylspiro[aziridine-2,2′-indene]-1′,3′-dione is a kinetically controlled product of this reaction and appears to act as a 1,3-dipole precursor. This theoretical study also shed light on the main transformations of the azomethine ylide derived from ninhydrin and sarcosine such as a 1,3-dipolar cycloaddition to cyclopropene dipolarophiles, a dimerization reaction and a (1+5) electrocyclization reaction. The antitumor activity of some synthesized compounds against cervical carcinoma (HeLa ) cell line was evaluated in vitro by MTS-assay.
AB - The multi-component 1,3-dipolar cycloaddition of ninhydrin, α-amino acids (or peptides), and cyclopropenes for the synthesis of spirocyclic heterocycles containing both 3-azabicyclo[3.1.0]hexane and 2 H -indene-1,3-dione motifs has been developed. This method provides easy access to 3-azabicyclo[3.1.0]hexane-2,2′-indenes with complete stereoselectivity and a high degree of atom economy under mild reaction conditions. A broad range of cyclopropenes and α-amino acids have been found to be compatible with the present protocol, which offers an opportunity to create a new library of biologically significant scaffold (3-azabicyclo[3.1.0]hexane). In addition, the сomprehensive study of mechanism of azomethine ylide formation from ninhydrin and sarcosine was performed by means of M11 density functional theory (DFT) calculations. It has been revealed that experimentally observed 1-methylspiro[aziridine-2,2′-indene]-1′,3′-dione is a kinetically controlled product of this reaction and appears to act as a 1,3-dipole precursor. This theoretical study also shed light on the main transformations of the azomethine ylide derived from ninhydrin and sarcosine such as a 1,3-dipolar cycloaddition to cyclopropene dipolarophiles, a dimerization reaction and a (1+5) electrocyclization reaction. The antitumor activity of some synthesized compounds against cervical carcinoma (HeLa ) cell line was evaluated in vitro by MTS-assay.
KW - DFT calculations
KW - antitumor activity
KW - cervical carcinoma (HeLa) cell line
KW - cyclopropenes
KW - peptides
KW - reaction mechanism
KW - stereoselectivity
KW - α-amino acids
KW - alpha-amino acids
UR - http://www.scopus.com/inward/record.url?scp=85100927292&partnerID=8YFLogxK
UR - https://www.mendeley.com/catalogue/ae8c1fed-588b-3ba5-974f-8711affbd927/
U2 - 10.1055/a-1360-9716
DO - 10.1055/a-1360-9716
M3 - Article
VL - 53
SP - 2114
EP - 2132
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 12
ER -
ID: 74412098