Email this article Synthesis of dispirooxindoles containing N-unsubstituted heterocyclic moieties and study of their anticancer activity
- Authors: Beloglazkina A.A.1, Karpov N.A.1, Mefedova S.R.1, Polyakov V.S.1, Skvortsov D.A.1, Kalinina M.A.1,2, Tafeenko V.A.1, Majouga A.G.1,3, Zyk N.V.1, Beloglazkina E.K.1
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Affiliations:
- Department of Chemistry, M. V. Lomonosov Moscow State University
- Skolkovo Institute of Science and Technology, Territory of the Skolkovo Innovation Center
- D. Mendeleev University of Chemical Technology of Russia
- Issue: Vol 68, No 5 (2019)
- Pages: 1006-1013
- Section: Full Article
- URL: https://journals.rcsi.science/1066-5285/article/view/243372
- DOI: https://doi.org/10.1007/s11172-019-2511-6
- ID: 243372
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Abstract
A convenient method is proposed for the synthesis of N-unsubstituted spiroxindoles with different heterocyclic moieties (2-thiohydantoin, hydantoin, and thiazolidine) by the regio-selective 1,3-dipolar cycloaddition of azomethine ylides, generated from isatins and sarcosine, to arylidene derivatives of corresponding heterocycles. The cytotoxicity of compounds was tested by the MTT method against MCF7, A549, HEK, and VA13 cell lines and compared with the anticancer drug Nutlin-3a. The best bioactivity was observed for hydantoin-based dispiroindolinones, the most cytotoxic compound demonstrated selectivity against A549 lung cancer cells with an IC50 value of 6.6±1.6 μmol L−1.
About the authors
A. A. Beloglazkina
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: izvan@ioc.ac.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119191
N. A. Karpov
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: izvan@ioc.ac.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119191
S. R. Mefedova
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: izvan@ioc.ac.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119191
V. S. Polyakov
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: izvan@ioc.ac.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119191
D. A. Skvortsov
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: izvan@ioc.ac.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119191
M. A. Kalinina
Department of Chemistry, M. V. Lomonosov Moscow State University; Skolkovo Institute of Science and Technology, Territory of the Skolkovo Innovation Center
Email: izvan@ioc.ac.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119191; 1 Build., 30 Bolshoi bul’var, Moscow, 121205
V. A. Tafeenko
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: izvan@ioc.ac.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119191
A. G. Majouga
Department of Chemistry, M. V. Lomonosov Moscow State University; D. Mendeleev University of Chemical Technology of Russia
Email: izvan@ioc.ac.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119191; 9 Miusskaya pl., Moscow, 125047
N. V. Zyk
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: izvan@ioc.ac.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119191
E. K. Beloglazkina
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: izvan@ioc.ac.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119191
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