title: Substituted N-aminothioglycolurils containing thiosemicarbazone moiety and their cytotoxic activity in vitro.
abstract: 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[Formula: see text] 23.7, and 6.4 [Formula: see text]M, respectively). The IC[Formula: see text] value of thioglycoluril 1f against normal human embryonic kidney cells HEK293 was 72.5 [Formula: see text]M, which appeared to be 3-11-fold higher than IC[Formula: see text] values of 1f against human cancer cells.
authors.affiliation: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation. gaz@ioc.ac.ru.
authors.forename: Galina A
authors.initials: GA
authors.lastname: Gazieva
authors.affiliation: Institute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka, Russian Federation.
authors.forename: Lada V
authors.initials: LV
authors.lastname: Anikina
authors.affiliation: Institute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka, Russian Federation.
authors.forename: Sergei A
authors.initials: SA
authors.lastname: Pukhov
authors.affiliation: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation.
authors.forename: Tatyana B
authors.initials: TB
authors.lastname: Karpova
authors.affiliation: A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russian Federation.
authors.forename: Yulia V
authors.initials: YV
authors.lastname: Nelyubina
authors.affiliation: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation.
authors.forename: Angelina N
authors.initials: AN
authors.lastname: Kravchenko
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013882:Thiosemicarbazones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D013882:Thiosemicarbazones
keywords: 5-Thioxohexahydroimidazo[45-d]imidazol-2(1H)-one; Cyclic thiosemicarbazones; Cytotoxic activity; Thioglycolurils