Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Concise Synthesis of Tryptanthrin Spiro Analogues with In Vitro Antitumor Activity Based on One-Pot, Three-Component 1, 3-Dipolar Cycloaddition of Azomethine Ylides to Сyclopropenes. / Filatov, Alexander S. ; Knyazev, Nickolay A. ; Shmakov, Stanislav V.; Bogdanov, Alexey A; Ryazantsev, Mikhail N; Shtyrov, Andrey A.; Starova, Galina L. ; Molchanov, Alexander P. ; Larina, Anna G. ; Boitsov, Vitali M.; Stepakov, Alexander V. .
в: Synthesis, Том 51, № 3, 2019, стр. 713-729.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
}
TY - JOUR
T1 - Concise Synthesis of Tryptanthrin Spiro Analogues with In Vitro Antitumor Activity Based on One-Pot, Three-Component 1, 3-Dipolar Cycloaddition of Azomethine Ylides to Сyclopropenes
AU - Filatov, Alexander S.
AU - Knyazev, Nickolay A.
AU - Shmakov, Stanislav V.
AU - Bogdanov, Alexey A
AU - Ryazantsev, Mikhail N
AU - Shtyrov, Andrey A.
AU - Starova, Galina L.
AU - Molchanov, Alexander P.
AU - Larina, Anna G.
AU - Boitsov, Vitali M.
AU - Stepakov, Alexander V.
PY - 2019
Y1 - 2019
N2 - A simple, efficient and atom-economic method has been developed for the synthesis of complex alkaloid-like compounds with spiro-fused indolo[2,1-b]quinazoline and cyclopropa[a]pyrrolizine or 3-azabicyclo[3.1.0]hexane moieties. We have found that one-pot, three-component 1,3-dipolar cycloaddition reactions allow the desired products to be obtained from various cyclopropene derivatives with tryptanthrin-derived azomethine ylides generated in situ, in good to high yields and excellent diastereoselectivity. The possibility of ylide generation was exemplified by using α-amino acids (l-proline, l-4-thiazolidincarboxylic acid) and simplest peptides (dipeptide Gly-Gly, tripeptide Gly-Gly-Gly). Quantum chemical investigations indicate that the reaction proceeds through the S-shaped azomethine ylide, the interaction of which with cyclopropenes proceeds via a less sterically hindered endo-transition state. The antitumor activity of some of spiro-tryptanthrin derivatives against erythroleukemia (K562), cervical carcinoma (HeLa) and colon carcinoma (CT26) cell lines was evaluated in vitro by MTS-assay.
AB - A simple, efficient and atom-economic method has been developed for the synthesis of complex alkaloid-like compounds with spiro-fused indolo[2,1-b]quinazoline and cyclopropa[a]pyrrolizine or 3-azabicyclo[3.1.0]hexane moieties. We have found that one-pot, three-component 1,3-dipolar cycloaddition reactions allow the desired products to be obtained from various cyclopropene derivatives with tryptanthrin-derived azomethine ylides generated in situ, in good to high yields and excellent diastereoselectivity. The possibility of ylide generation was exemplified by using α-amino acids (l-proline, l-4-thiazolidincarboxylic acid) and simplest peptides (dipeptide Gly-Gly, tripeptide Gly-Gly-Gly). Quantum chemical investigations indicate that the reaction proceeds through the S-shaped azomethine ylide, the interaction of which with cyclopropenes proceeds via a less sterically hindered endo-transition state. The antitumor activity of some of spiro-tryptanthrin derivatives against erythroleukemia (K562), cervical carcinoma (HeLa) and colon carcinoma (CT26) cell lines was evaluated in vitro by MTS-assay.
KW - One-pot synthesis
KW - Azomethine ylides
KW - 1,3-Dipolar cycloaddition
KW - cyclopropenes
KW - tryptanthrin
KW - α-amino acids
KW - peptides
UR - https://thieme-connect.com/products/ejournals/abstract/10.1055/s-0037-1611059
U2 - 10.1055/s-0037-1611059
DO - 10.1055/s-0037-1611059
M3 - Article
VL - 51
SP - 713
EP - 729
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 3
ER -
ID: 36473667