109754-07-6

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 95378-36-2 diethyl 2,4-dioxoimidazolidin-5-yl-phosphonate 
• 461-72-3 2,4-imidazolidinedione 
• 120697-21-4 5-(4-methyl-benzylidene)-imidazolidine-2,4-dione 
• 139488-41-8 3-Acetyl-2-thioxo-5-[1-p-tolyl-meth-(Z)-ylidene]-imidazolidin-4-one 

Downstream Products

• 120697-21-4 5-(4-methyl-benzylidene)-imidazolidine-2,4-dione 

Relevant academic research and scientific papers

Enantioselective Synthesis of Chiral Substituted 2,4-Diketoimidazolidines and 2,5-Diketopiperazines via Asymmetric Hydrogenation

An enantioselective hydrogenation of 5-alkylidene-2,4-diketoimidazolidines (hydantoins) and 3-alkylidene-2,5-ketopiperazines catalyzed by the Rh/f-spiroPhos complex under mild conditions has been developed, which provides an efficient approach to the highly enantioselective synthesis of chiral hydantoins and 2,5-ketopiperazine derivatives with high enantioselectivities up to 99.9% ee.

Sulfated and Oxygenated Imidazoline Derivatives: Synthesis, Antioxidant Activity and Light-Mediated Antibacterial Activity

Imidazoline derivatives with different exocyclic substituents were simply prepared from common starting materials. The procedures were carried out in an eco-friendly manner. The antioxidant activity of these derivatives was explored by different experimental assays, such as ABTS.+ and DPPH. scavenging assay, as well as reducing power assay. The structural differences are discussed in terms of the results. Sulfur analogs showed higher antioxidant activity than their oxygenated counterparts. The same tendency was observed in microbiological studies, in which the same imidazoline compounds were assayed for light-mediated activity against of Staphylococcus aureus and Escherichia coli strains. A light-enhanced activity was observed for almost all the sulfated imidazolines after exposure to UV-A (400-320 nm) light.

Privileged scaffolds or promiscuous binders: A comparative study on rhodanines and related heterocycles in medicinal chemistry

Rhodanines and related five-membered heterocycles with multiple heteroatoms have recently gained a reputation of being unselective compounds that appear as "frequent hitters" in screening campaigns and therefore have little value in drug discovery. However, this judgment appears to be based mostly on anecdotal evidence. Having identified various rhodanines and related compounds in screening campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed. The results indicate that the exocyclic, double bonded sulfur atom in rhodanines and thiohydantoins, in addition to other structural features, offers a particularly high density of interaction sites for polar interactions and hydrogen bonds. This causes a promiscuous behavior at concentrations in the "screening range" but should not be regarded as a general knockout criterion that excludes such screening hits from further development. It is suggested that special criteria for target affinity and selectivity are applied to these classes of compounds and that their exceptional and potentially valuable biomolecular binding properties are consequently exploited in a useful way.

Synthesis and reactivity of 5-methylenehydantoins

5-Methylenehydantoin, as well as the N-mono- and N,N-di-protected derivatives, can be obtained by different synthetic routes. These compounds can undergo a large variety of reactions, such as Diels-Alder, epoxidation, methanol addition and conjugate addition reactions of different types of nucleophiles, including carbon (cyanide), nitrogen (piperidine) and sulfur (thiols, thioacetate) nucleophiles. The reactivity with electrophilic reagents, such as m-CPBA or methanol in acidic medium, and the need for Lewis acids to promote the conjugate addition reactions indicate that hydantoin is a poor electron-withdrawing group.

Microwave-assisted solvent-free regiospecific synthesis of 5-alkylidene and 5-arylidenehydantoins

Hydantoins have become a well-known class of structures that have found significant applications as agrochemicals and therapeutics. This structural motif is of interest in the synthesis of small building blocks suitable for the preparation of potentially

Anticonvulsant Activity of Phenylmethylenehydantoins: A Structure-Activity Relationship Study

Phenylmethylenehydantoins (PMHs) and their des-phenyl analogues were synthesized and evaluated for anticonvulsant activity using the maximal electroshock seizure (MES) assay. The phenyl rings of PMHs were substituted with a wide spectrum of groups, and th

A new approach for the conversion of thiohydantoin to hydantoin derivatives

The reaction of thiohydantoins with 1-(bromoacetyl)benzenes afforded the corresponding hydantoin derivatives and 1-(mercaptoacetyl)benzenes instead of the expected oxoimidazothiazoles.

Thermal Equilibration of Z- and E-Isomers of 5-Arylmetylenehydantoins. Evidence for Non-bonded Aromatic ?...Methyl Attractions

Standard free energy differences between the Z- and E-isomers of 14 5-arylmethylenehydantoins have been estimated by thermal equilibration in dimethyl sulphoxide.The Z-configuration is more stable for the N-substituted compounds while the E-configuration is preferred for those N-1 methyl derivatives with only para-substituents in the aryl group.The ΔG0 values vary with the nature of the para substituents.For those N-1 methyl derivatives with two ortho-substituents in the aryl group, the configurational preference is dependent on the electronic effects of these aryl subtituents, suggesting the presence of non-bonded aromatic ?...Me interactions.The factors influencing the relative stabilities of Z- and E-isomers are discussed.