976-85-2

Basic information

• Product Name: ethyl (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)acetate
• CAS NO: 976-85-2
• Molecular Formula: C₁₉H₁₈N₂O₄
• Molecular Weight: 338.3572
• Mol File: 976-85-2.mol
• Article Data: 6

Chemical Properties

• Density: 1.254g/cm³
• Refractive Index: 1.583
• CAS DataBase Reference: ethyl (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)acetate(976-85-2)
• EPA Substance Registry System: ethyl (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)acetate(976-85-2)

Safety Data

• Hazardous Substances Data: 976-85-2(Hazardous Substances Data)

Upstream product

• 57-41-0 phenythoin 
• 105-36-2 ethyl bromoacetate 
• 134-81-6 benzil 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 100-52-7 benzaldehyde 
• 105-39-5 chloroacetic acid ethyl ester 
• 630-93-3 sodium phenytoin 

Downstream Products

• 1426998-93-7 C₁₈H₁₄N₄O₃S 
• 1426998-88-0 C₂₀H₂₁N₅O₃S 
• 1426998-89-1 C₂₄H₂₁N₅O₃S 
• 1426998-91-5 C₂₅H₂₃N₅O₄S 
• 1426998-78-8 C₂₀H₁₉N₅O₂S 
• 1426998-79-9 C₂₄H₁₉N₅O₂S 
• 1426998-80-2 C₂₅H₂₁N₅O₂S 
• 1426998-81-3 C₂₅H₂₁N₅O₃S 
• 1426998-82-4 C₂₄H₁₈ClN₅O₂S 
• 1426998-83-5 C₂₀H₁₉N₅O₂S 
• 1426998-84-6 C₂₄H₁₉N₅O₂S 
• 1426998-85-7 C₂₅H₂₁N₅O₂S 
• 1426998-86-8 C₂₅H₂₁N₅O₃S 
• 1426998-87-9 C₂₄H₁₈ClN₅O₂S 

Relevant articles and documents

Synthesis and characterization of new 5,5′-dimethyl- and 5,5′-diphenylhydantoin-conjugated hemorphin derivatives designed as potential anticonvulsant agents

Herein, the synthesis and characterization of some novel N-modified hybrid analogues of hemorphins containing a C-5 substituted hydantoin residue as potential anticonvulsants and for the blockade of sodium channels are presented. Their structure-property relationships are highlighted by electrochemical and Fourier transform infrared spectroscopy (FT-IR) analysis methods. The lipophilicity and molecular docking of voltage-gated sodium channels were also determined. The new series of 5,5′-dimethyl- and 5,5′-diphenylhydantoin-conjugated hemorphin derivatives were obtained as C-terminal amides via solid-phase peptide synthesis, an Fmoc-strategy using 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU). The anticonvulsant activity of the hybrid-peptides (0.25, 0.5 and 1 μg) was tested by maximal electroshock (MES) and 6 Hz psychomotor seizure tests using male ICR mice. None of the compounds tested showed neurotoxicity in the rotarod test. The reference drug phenytoin was used as a positive control. The most active compound Ph-5 showed 100% efficacy against the 6 Hz-induced psychomotor seizures at a dose of 1.0 μg and tonic seizures in the MES test at a lower dose of 0.5 μg. This analogue of VV-hemorphin-5 contained a 5,5′-diphenylhydantoin residue at the N-terminus and a hydrophobic Val-Val-Tyr-Pro-Trp-Thr-Gln-CONH2 amino acid sequence of the peptide molecule. The quantitative data for the 6 Hz test demonstrated that the peptide Ph-5 exhibited a median effective dose (ED50) value of 0.358 μg and PI >13.97, and ED50 of 0.25 μg and PI >20.35 in the MES test, respectively. Results from the docking study suggest that the neuropeptide Ph-5 is a potent inhibitor of sodium channels, and blockade of voltage-gated sodium channels could be the mechanism of action of the hybrid-peptide derivatives with anticonvulsant activity.

Synthesis and anticonvulsant activity of new phenytoin derivatives

Hybrids between phenytoin and thiosemicarbazide, 1,3,4-oxadiazole, 1,3,4-thiadiazole or 1,2,4-triazole were synthesized and tested for anticonvulsant activity. Preliminary anticonvulsant screening was performed using standard maximal electroshock (MES) an

SOME EXAMPLES OF 5,5-DIPHENYLHYDANTOIN ALKYLATION

The method of N1 and N3 alkylation of 5,5-diphenylhydantoin has been described for some examples.The synthesis of only N1 alkylated compound 11 has been accomplished with ethoxycarbonyl as the N3 protecting grou