Substituted N-aminothioglycolurils containing thiosemicarbazone moiety and their cytotoxic activity in vitro

Substituted N-aminothioglycolurils containing thiosemicarbazone moiety and their cytotoxic activity in vitro Full article

Journal

Molecular Diversity
ISSN: 1573-501X , E-ISSN: 1381-1991

Output data

Year: 2016, Volume: 20, Number: 4, Pages: 837-846 Pages count : 10 DOI: 10.1007/s11030-016-9671-1

Authors

Gazieva Galina A. ¹ , Anikina Lada V. ² , Pukhov Sergei A. ² , Karpova Tatyana B. ¹ , Nelyubina Yulia V. ³ , Kravchenko Angelina N. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
2	Institute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka, Russian Federation
3	A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russian Federation

A library of hybrid molecules bearing thioglycoluril and (hetero)aromatic aldehyde thiosemicarbazone moieties was synthesized via a tandem hydrazone formation—ring contraction reaction of 5,7-dialkyl-3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-ones with (hetero)aromatic aldehydes. All synthesized compounds were tested for their cytotoxic activity against rhabdomyosarcoma, A549, and MS human cancer cell lines by MTT-assay. Among the derivatives, (E)-4-benzylideneamino-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 1f was found to have the most marked antiproliferative activity toward the tested cell lines (1f: IC 23.7, and 6.4 μM, respectively). The IC value of thioglycoluril 1f against normal human embryonic kidney cells HEK293 was 72.5 μM, which appeared to be 3–11-fold higher than IC values of 1f against human cancer cells.

Gazieva G.A. , Anikina L.V. , Pukhov S.A. , Karpova T.B. , Nelyubina Y.V. , Kravchenko A.N.
Substituted N-aminothioglycolurils containing thiosemicarbazone moiety and their cytotoxic activity in vitro
Molecular Diversity. 2016. V.20. N4. P.837-846. DOI: 10.1007/s11030-016-9671-1 WOS Scopus OpenAlex

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