Synthesis and cytotoxicity of novel oxindoles dispiro derivatives with thiohydantoin and adamantane fragments

Submitting author affiliation:
Moscow State University, Moscow, Russian Federation

Beilstein Arch. 2019, 2019143.

Published 11 Nov 2019

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An effective and highly regio- and diastereoselective one-pot synthesis of two type of dispiro heterocyclic systems (2-thioxodispiro[imidazolidine-4,3'-pyrrolidine-2',3''-indoline]-2'',5-diones and 2-thioxodispiro[imidazolidine-4,3'-pyrrolidine-4',3''-indoline]-2'',5-diones) comprising pyrrolidinyloxindole, thiohydantoin and adamantane moieties have been developed based on a 1,3-dipolar cycloaddition of azomethine ylides, generated from isatin and sarcosine or formaldehyde and sarcosine, to adamantine-containing electron-deficient alkenes. Several molecules have demonstrated a considerable cytotoxicity against and A549, HEK293T, MCF7 and VA13 cancer cell lines. The possible mechanism of anticancer activity of synthesised compounds based on literature data may be the inhibition of p53/MDM2 interaction, however, we did not observe significant p53 activation using a reporter construction in A549 cell line in a relevant concentration range.

Keywords: adamantanes; 1,3-dipolar cycloaddition; dispiro-oxindoles; thiohydantoins

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Kukushkin, M. E.; Skvortsov, D. A.; Kalinina, M. A.; Tafeenko, V. A.; Burmistrov, V. V.; Butov, G. M.; Zyk, N. V.; Majouga, A. G.; Beloglazkina, E. K. Beilstein Arch. 2019, 2019143. doi:10.3762/bxiv.2019.143.v1

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