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1H-NMR spectroscopy was used to monitor the reactions of an arylidene 2-thiohydantoin derivative, 3-((phenylmethylene)amino)-2-thioxo-4-imidazolidinone (3), with PdCl2, cis-[PdCl2(dmso-S)2] and K2[PdCl4] in DMSO-d6 in order to elucidate the reaction kinetics and mechanism. The 2-thiohydantoin derivative 3 formed cis-[Pd(3-N,S)(dmso-S)2]+ complex (5) in reactions with PdCl2 and cis-[PdCl2(dmso-S)2], while no reaction with K2[PdCl4] was observed. A two-step mechanism for the reactions of 3 with PdCl2 and cis- -[PdCl2(dmso-S)2] is proposed, in which fast coordination to the side chain nitrogen occurs in the first step, while chelation and coordination to the sulfur atom in the 2-thiohydantoin ring is the second, slower, rate-determining step. The reaction rate constants were calculated and reactivities of the 2-thiohydantoin derivative 3 towards the palladium(II) salts were compared and discussed. Reaction of 3 with cis-[PdCl2(dmso-S)2] was faster than with PdCl2. The investigated palladium(II) salts also react with the solvent, DMSO-d6, and the influence of these side reactions on the outcome and kinetics of the 2-thiohydantoin derivative complexation reaction is discussed in detail. The obtained results of this study can have an impact in explanation of the coordination behavior of antitumor active palladium(II) and platinum(II) complexes.

A series of zingerone–thiohydantoin hybrids were synthesized from O-alkyl zingerone derivatives by cyclocondensation with thiosemicarbazide in a two-step reaction. The obtained new potentially bioactive compounds were structurally characterized by IR and NMR spectroscopy, as well as by elemental and HRMS analysis. In addition, their antimicrobial and in vitro anticancer activities were tested. The tested compounds showed low to moderate antimicrobial activity. Zingerone–thiohydantoin hybrid with an O-butyl substituent exerted the significant cytotoxic activity on colon HCT-116 cancer cells, without toxicity on healthy MRC-5 cells.

Several 2-thiohydаntоin–Shiff base derivatives were prepared as ecofriendly corrosion inhibitors for mild steel in acid environment. Their anticorrosion properties were studied on mild steel in 0.5 M HCl solution as corrosion electrolyte by using usuаl grаvimеtriс and different elесtrосhemicаl techniques (wеight lоss mеаsurеmеnt, pоtеntiоdynаmiс pоlаrizаtiоn and pоtеntiоstаtiс еlесtrосhеmicаl impеdаnсе sресtrоscору). Mild steel surface was characterized using two analytical techniques, scanning electron microscopy for surface morphology and elemental composition and atomic force microscopy. The study has shown that the inhibiting action of these environmentally benign inhibitors synthesized from inexpensive commercially available starting materials could be attributed to adsorption on the metal surface.

A series of twenty two different imidazolidine-2,4-dione derivatives, divided according to their structure into five groups, including alkyl, alkenyl or aryl 5,5disubstituted hydantoins, spirohydantoins, and fused bicyclic and tricyclic hydantoins, was synthesized and examined for in vitro antimicrobial activity against 15 strains of bacteria and 4 strains of yeast. The antimicrobial activity was evaluated by the determination of the minimal inhibitory concentration (MIC) and the minimal microbicidal concentration (MMC) using the microdilution method. The assayed compounds exerted moderate antibacterial and weak antifungal activity. The antimicrobial activities were influenced by the structure and concentration of the tested compounds as well as the type of test microorganisms. The fused bicyclic hydantoin derivatives obtained by organoselenium induced intramolecular cyclization exhibited the highest inhibitory activity. The examined hydantoin derivatives seem as drug-like candidate for further evaluation of biological activities.

5-Alkenyl hydantoins and alkenyl spirohydantoins are converted into bicyclic and tricyclic hydantoins, under indirect electrochemical conditions, generating the phenylselenyl cation in situ. The reactions proceeded in good to exelent yields. The influence of electrochemical conditions on regio- and diastereoselectivity of the selenocyclization reactions is investigated.

The 3-arylidene-2-thiohydantoin derivative, 3-[(2-hydroxybenzylidene) amino]-2-thioxoimidazolidin-4-one, was synthesized in a two-step condensation reaction of 2-hydroxybenzaldehyde, thiosemicarbazide and ethyl chloroacetate. The ligand was structurally characterized by NMR and IR spectroscopy, as well as by elemental analysis. In the reaction of the well-known polymeric trans-[CuCl2(DMSO)2]n complex with the polydentate thiohydantoin type ligand, instead of the corresponding copper thiohydantoin complex, unexpectedly, the dinuclear cis-[{CuCl(DMSO)2}(μ-Cl)]2 complex (1) was formed predominantly as the final stable product. The structure of the complex 1 was confirmed by single crystal X-ray diffraction analysis. The cis-complex is obtained through assisted isomerization of the trans-form, in which the thiohydantoin derivative has a crucial role.

5-Alkenyl hydantoins and alkenyl spirohydantoins are converted into bicyclic and tricyclic hydantoins, under indirect electrochemical conditions, generating the phenylselenyl cation in situ. The reactions proceeded in good to exelent yields. The influence of electrochemical conditions on regioand diastereoselectivity of the selenocyclization reactions is investigated. [ABSTRACT FROM AUTHOR]

The 3-arylidene-2-thiohydantoin derivative, 3-[(2-hydroxybenzylidene) amino]-2-thioxoimidazolidin-4-one, was synthesized in a two-step condensation reaction of 2-hydroxybenzaldehyde, thiosemicarbazide and ethyl chloroacetate. The ligand was structurally characterized by NMR and IR spectroscopy, as well as by elemental analysis. In the reaction of the well-known polymeric trans-[CuCl2(DMSO)2]n complex with the polydentate thiohydantoin type ligand, instead of the corresponding copper thiohydantoin complex, unexpectedly, the dinuclear cis-[{CuCl(DMSO)2}(μ-Cl)]2 complex (1) was formed predominantly as the final stable product. The structure of the complex 1 was confirmed by single crystal X-ray diffraction analysis. The cis-complex is obtained through assisted isomerization of the trans-form, in which the thiohydantoin derivative has a crucial role. [ABSTRACT FROM AUTHOR]