Synthesis and antiviral activity of bis-spirocyclic derivatives of rhodanine

Bis-spiro heterocycles containing spiro units at the 1,3-positions of the pyrrolizidine (isothiapyrrolizidine) moiety were synthesized by the reaction of unstabilized azomethine ylides, which were generated in situ from isatin and proline (isothiaproline), with hetarylidene-substituted rhodanines. Q...

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Bibliographic Details
Published in:Russian chemical bulletin 2014-05, Vol.63 (5), p.1130-1136
Main Authors: Kurbatov, S. V., Zarubaev, V. V., Karpinskaya, L. A., Shvets, A. A., Kletsky, M. E., Burov, O. N., Morozov, P. G., Kiselev, O. I., Minkin, V. I.
Format: Article
Language:English
Subjects:
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Cycloaddition
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Inorganic Chemistry
Organic Chemistry
Potential energy
Proline
Quantum chemistry
Regioselectivity
Viruses
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Summary:Bis-spiro heterocycles containing spiro units at the 1,3-positions of the pyrrolizidine (isothiapyrrolizidine) moiety were synthesized by the reaction of unstabilized azomethine ylides, which were generated in situ from isatin and proline (isothiaproline), with hetarylidene-substituted rhodanines. Quantum chemical calculations of potential energy surface sections and descriptors controlling the regioselectivity of cycloaddition were carried out. For a number of compounds in vitro activity against the influenza virus A/California/07/09 (H1N1)pdm2009 was experimentally established.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-014-0560-4