Synthesis of dispirooxindoles containing N-unsubstituted heterocyclic moieties and study of their anticancer activity


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Resumo

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.

Sobre autores

A. Beloglazkina

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: izvan@ioc.ac.ru
Rússia, 3 Build., 1 Leninskie Gory, Moscow, 119191

N. Karpov

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: izvan@ioc.ac.ru
Rússia, 3 Build., 1 Leninskie Gory, Moscow, 119191

S. Mefedova

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: izvan@ioc.ac.ru
Rússia, 3 Build., 1 Leninskie Gory, Moscow, 119191

V. Polyakov

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: izvan@ioc.ac.ru
Rússia, 3 Build., 1 Leninskie Gory, Moscow, 119191

D. Skvortsov

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: izvan@ioc.ac.ru
Rússia, 3 Build., 1 Leninskie Gory, Moscow, 119191

M. 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
Rússia, 3 Build., 1 Leninskie Gory, Moscow, 119191; 1 Build., 30 Bolshoi bul’var, Moscow, 121205

V. Tafeenko

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: izvan@ioc.ac.ru
Rússia, 3 Build., 1 Leninskie Gory, Moscow, 119191

A. Majouga

Department of Chemistry, M. V. Lomonosov Moscow State University; D. Mendeleev University of Chemical Technology of Russia

Email: izvan@ioc.ac.ru
Rússia, 3 Build., 1 Leninskie Gory, Moscow, 119191; 9 Miusskaya pl., Moscow, 125047

N. Zyk

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: izvan@ioc.ac.ru
Rússia, 3 Build., 1 Leninskie Gory, Moscow, 119191

E. Beloglazkina

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: izvan@ioc.ac.ru
Rússia, 3 Build., 1 Leninskie Gory, Moscow, 119191

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