title: Synthesis of Functionalized 3-Spiro[cyclopropa[a]pyrrolizine]- and 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3 + 2]-Cycloaddition.
abstract: 3-Spiro[cyclopropa[a]pyrrolizine]- and 3-spiro[3-azabicyclo[3.1.0]hexane]oxindoles were prepared in moderate to high yields via one-pot three-component reactions using substituted isatins, α-amino acids, and cyclopropenes. The key step is an intramolecular [3 + 2]-cycloaddition reaction of an in situ generated azomethine ylide onto a cyclopropene. Both N-substituted and N-unsubstituted α-amino acids, dipeptide Gly-Gly, and also benzylamine were used as the amine component for the azomethine ylide generation. The anticancer activity of some of the obtained compounds against human leukemia K562 cell line was evaluated by flow cytometry in vitro.
authors.affiliation: Saint-Petersburg State University , 7/9 Universitetskaya nab., St. Petersburg, 199034, Russian Federation.
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Filatov
authors.affiliation: Saint-Petersburg Academic University - Nanotechnology Research and Education Centre RAS , ul. Khlopina 8/3, St. Petersburg, 194021, Russian Federation.|Institute of Cytology of the Russian Academy of Science , Tikhoretsky pr. 4, St. Petersburg 194064, Russian Federation.
authors.forename: Nickolay A
authors.initials: NA
authors.lastname: Knyazev
authors.affiliation: Saint-Petersburg State University , 7/9 Universitetskaya nab., St. Petersburg, 199034, Russian Federation.
authors.forename: Alexander P
authors.initials: AP
authors.lastname: Molchanov
authors.affiliation: Saint-Petersburg State University , 7/9 Universitetskaya nab., St. Petersburg, 199034, Russian Federation.
authors.forename: Taras L
authors.initials: TL
authors.lastname: Panikorovsky
authors.affiliation: Saint-Petersburg State University , 7/9 Universitetskaya nab., St. Petersburg, 199034, Russian Federation.
authors.forename: Rafael R
authors.initials: RR
authors.lastname: Kostikov
authors.affiliation: Saint-Petersburg State University , 7/9 Universitetskaya nab., St. Petersburg, 199034, Russian Federation.
authors.forename: Anna G
authors.initials: AG
authors.lastname: Larina
authors.affiliation: Saint-Petersburg Academic University - Nanotechnology Research and Education Centre RAS , ul. Khlopina 8/3, St. Petersburg, 194021, Russian Federation.|Pavlov First Saint Petersburg State Medical University , ul. L'va Tolstogo 6/8, St. Petersburg 197022, Russian Federation.
authors.forename: Vitali M
authors.identifier: 0000-0002-4857-2046
authors.initials: VM
authors.lastname: Boitsov
authors.affiliation: Saint-Petersburg State University , 7/9 Universitetskaya nab., St. Petersburg, 199034, Russian Federation.|Voeikov Main Geophysical Observatory , ul. Karbysheva 7, St. Petersburg 194021, Russian Federation.
authors.forename: Alexander V
authors.identifier: 0000-0001-9470-1710
authors.initials: AV
authors.lastname: Stepakov