976-85-2

Upstream product

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

Downstream Products

• 92084-89-4 5,5-diphenyl-3-{2-oxo-2-[4-(2-hydroxyethyl)-1-piperazinyl]ethyl}hydantoin 
• 20000-16-2 3-N-(2-morpholinoethyl)-5,5-diphenylhydantoin 
• 23780-53-2 diethyl 2,2'-(2,4-dioxo-5,5-diphenylimidazolidine-1,3-diyl)diacetate 
• 1224-08-4 3-amino-5,5-diphenylimidazolidine-2,4-dione 
• 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 

Relevant academic research and scientific papers

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.

Direct N1-selective alkylation of hydantoins using potassium bases

Hydantoins, including the antiepileptic drug phenytoin, contain an amide nitrogen and an imide nitrogen, both of which can be alkylated. However, due to the higher acidity of its proton, N3 can be more easily alkylated than N1 under

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

Phenytoin-based bivalent ligands: Design, synthesis and anticonvulsant activity

Synthesis, characterization and anticonvulsant properties of new bivalent ligands derived from phenytoin were described. Initial anticonvulsant screening was performed using maximal electroshock (MES) and pentylenetetrazole (PTZ) screens in mice. The neurotoxicity for compounds that showed significant anticonvulsant activity was determined applying the rotorod test. Most of the test compounds were found to be effective in at least one seizure model in a dose of 100 mg/kg. Compound 5e exhibited marked anticonvulsant activity in both MES and PTZ screens. The computer-aided prediction of biological activity was carried out.

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

Acetohydroxamic acids

The invention provides new acetohydroxamic acid derivatives, having interesting properties on the central nervous system, of the formula: R1 R2 R3 C-CO-NHOH, in which R2 and R3 are each hydrogen or C1-6 alkyl, and R1 is C1-6 alkyl Z1 Z2 N (where Z1 and Z2 are each phenyl, substituted phenyl, or cycloalkyl), substituted hydantoinyl, benzhydroxylcarboxamido, Z3 CH2 -- (where Z3 = optionally substituted aryl), Z4 -A- (where Z4 is optionally substituted phenyl or naphthyl, and A is --NH--, --N(C1-4 alkyl)--, --N(C5-6 cycloalkyl)--, --NHCO--, --N(C1-4 alkyl)CO--, --N(C5-6 cycloalkyl)CO--, --CONH--, --CON(C1-4 alkyl)--, --CON(C5-6 cycloalkyl)--, --NHCONH--, --N(C5 H6)CONH--, or --N(substituted phenyl)CONH--, optionally substituted benzimidazolyl, or an optionally substituted tricyclic radical, and their metal and acid addition salts.