116705-22-7

Upstream product

• 68319-44-8 4-<(4-nitrophenyl)methyl>imidazolidine-2,5-dione 
• 136949-28-5 2-Amino-5-[1-(4-nitro-phenyl)-meth-(Z)-ylidene]-3,5-dihydro-imidazol-4-one 
• 555-16-8 4-nitrobenzaldehdye 
• 95378-36-2 diethyl 2,4-dioxoimidazolidin-5-yl-phosphonate 
• 133384-65-3 (5E)-5-(4-nitrobenzylidene)imidazolidine-2,4-dione 
• 3530-82-3 5-benzyl-hydantoin 
• 461-72-3 2,4-imidazolidinedione 

Downstream Products

• 1310744-72-9 (R,Z)-2-(3-(((4-((2,5-dioxoimidazolidin-4-ylidene)methyl)phenyl)amino)methyl)benzamido)pentanedioic acid 
• 1310744-70-7 (R,Z)-dimethyl 2-(3-(((4-((2,5-dioxoimidazolidin-4-ylidene)methyl)phenyl)amino)methyl)benzamido)pentanedioate 

Relevant academic research and scientific papers

Hydantoin-based molecular photoswitches

A new family of molecular photoswitches based on arylidenehydantoins is described together with their synthesis and photochemical and photophysical studies. A series of hydantoin derivatives have been prepared as single isomers using simple and versatile chemistry in good yields. Our studies show that the photostationary states of these compounds can be easily controlled by means of external factors, such as the light source or filters. Moreover, the detailed investigations proved that these switches are efficient (i.e., they make efficient use of the light energy, are high fatigue resistant, and are very photostable). In some cases, the switches can be completely turned on/off, a desirable feature for specific applications. A series of theoretical calculations have also been carried out to understand the photoisomerization mechanism at the molecular level.

Evaluation of michael-type acceptor reactivity of 5-benzylidenebarbiturates, 5-benzylidenerhodanines, and related heterocycles using NMR

Despite existing experimental and computational tools to assess the risk, the non-specific chemical modification of protein thiol groups remains a significant source of false-positive hits, particularly in academic drug discovery. Herein, we describe the

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.

Structure-based design of a new series of d-glutamic acid based inhibitors of bacterial UDP-N-acetylmuramoyl-l-alanine: D-glutamate ligase (MurD)

MurD ligase is one of the key enzymes participating in the intracellular steps of peptidoglycan biosynthesis and constitutes a viable target in the search for novel antibacterial drugs to combat bacterial drug-resistance. We have designed, synthesized, and evaluated a new series of d-glutamic acid-based Escherichia coli MurD inhibitors incorporating the 5-benzylidenethiazolidin-4- one scaffold. The crystal structure of 16 in the MurD active site has provided a good starting point for the design of structurally optimized inhibitors 73-75 endowed with improved MurD inhibitory potency (IC50 between 3 and 7 μM). Inhibitors 74 and 75 showed weak activity against Gram-positive Staphylococcus aureus and Enterococcus faecalis. Compounds 73-75, with IC 50 values in the low micromolar range, represent the most potent d-Glu-based MurD inhibitors reported to date.

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

TRIETHYLAMINE, ETHANOL- MEDIATED DISCIPLINED REACTIONS OF S-BENZYLISOTHIOURONIUM CHLORIDE WITH UNSATURATED 2-OXAZOLIN-5-ONES: SYNTHESIS OF (Z)-2-AMINO-4-ARYLMETHYLENE-2-IMIDAZOLIN-5-ONES, 5-BENZOYLAMINO-2-BENZYLTHIO-6-OXO-4,4-SPIROCYCLOHEXYL-1,4,5,6-TETRA

Triethylamine-mediated condensation of S-benzylisothiouronium chloride with (Z)-4-arylmethylene-2-phenyl-2-oxazolin-5-ones (4) in ethanol gives (Z)-2-amino-4-arylmethylene-2-imidazolin-5-ones (7), whereas the similar reaction with 4-cyclohexylidene-2-phen

Latent Inhibitors. Part 6. Inhibition of Dihydro-orotate Dehydrogenase by Substituted 5-Benzylhydantoins

A series of substituted 5-benzyl-3-(1-carboxy-2-phenylethyl)hydantoins was prepared by condensation of aromatic aldehydes with the corresponding 5-unsubstituted hydantoin followed by reduction of the intermediate benzylidene derivative.The compounds were