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Oxazoline derivatives were mainly obtained from the O-tosyl-N-acyl-β-hydroxy amino acid peptides by β-elimination reaction. Dehydroalanine or hydantoin derivatives were isolated when the urethane type acyl groups were used.

In 1-arylhydantoins an o-methyl group is effectively larger than an o-chloro substituent in restricting rotation about the aryl-C—N bond, whereas in 3-arylhydantoins and 3-aryl-2-thiohydantoins the...

Pharmacokinetics and bioavailability for the 1-benzenesulfonylhydantoin derivatives and 1-unsubstituted hydantoin derivatives were evaluated from the plasma concentrations after oral and intravenous administrations to dogs. Apparent volume of distribution of the 1-benzenesulfonylhydantoin derivatives was about 0.25 l/kg, while that of the 1-unsubstituted hydantoin derivatives was about 1.3 l/kg. The result suggests that introduction of the benzenesulfonyl group at 1-position of the hydantoin ring has marked effect on the distribution into the fluids and tissues of the body. Bioavailabilities of sodium 5,5-diphenylhydantoin and sodium 1-benzenesulfonyl-5,5-diphenylhydantoin exceeded those of their corresponding free forms. The results were well explicable in terms of the excellent dissolution behaviours of the salt forms. The bioavailabilities of 5-ethyl-5-phenylhydantoin and 1-benzenesulfonyl-5-ethyl-5-phenylhydantoin were almost perfect. The results suggest that the dissolution rate is a rate-determining step in the bioavailability of the derivatives having two phenyl groups at 5-position of the hydantoin ring, irrespective of the presence of the benzenesulfonyl group at 1-position.

Treatment of 5-arylazo-2-thiohydantoins with aqueous sodium hydroxide affected hetero-ring opening followed by recyclization via the loss of hydrogen sulphide with the formation of 1-aryl-Δ2 -1, 2, 4-triazole-5-imino-3-carboxylic acids.

Standard free energy differences between the Z- and E-isomers of 14 hydantoins such as (I) and (II) are estimated by thermal equilibration in DMSO.

Die Hydantoinverbindungen (Ib)-(le) und (II) werden nach bekannten Syntheseverfahren hergestellt und bezuglich ihrer schistosomiziden Wirkung mit dem bereits bekannten, sehr aktiven 4-Chlorphenylderivat (Ia) verglichen.

The cyclization of N-alkylated (arylated) α-ureidocarboxylic acids gives a series of 3-mono- and 3,5-disubstituted hydantoins, and nitrosation of the latter yields their nitroso derivatives. The rotational isomerism of 3-(α-naphthyl)hydantoins has been studied by PMR spectroscopy.

Proton magnetic resonance spectra of methylthiohydantoin (3-methyl-2-thiohydantoin), thiohydantoin (2-thiohydantoin), and hydantoin derivatives of amino acids were studied in dimethyl sulfoxide-d6. Their parent amino acids could be identified by the spectra. An application to the N- and C-terminal amino acid analysis of a tripeptide was examined.

Department of Chemistry, University of Rajasthan, Jaipur-302 004 Manuscript received 10 November 1988, accepted 26 June 1989 The mass spectral decomposition modes of various hydantoin derivatives containing C-5 fluoroaryl, N-aryl, N-3 dialkylaminomethyl, N-3 chloroacetyl and N-3 dialkylamino­acetyl substituents have been investigated. 11C nmr spectral studies of some of the representative compounds have also been discussed.

A description has been given of a semi-automatic procedure for the analysis of a mixture of hydantoin derivatives of sixteen of the most common amino acids, thus improving the Stark and Smyth method for the determination of NH 2 -terminal residues in proteins and peptides.

Das Hydantoin (I) reagiert mit 1 Mol der Epoxide (II) in Gegenwart von LiCl oder KCl als Katalysator in DMF, Wasser oder ohne Losungsmittel zu den Monohydroxyalkyl-hydantoinen (III) (70-80% Ausbeute), wahrend bei Reaktion mit einem weiteren Mol (II) die Bis-hydroxyalkyl-Derivate (IV) (75-90%) entstehen.

The search for a medicament with sedative and relaxant properties has been a never-ending one in the progress of medicine. The earlier agents used included paraldehyde, chloral hydrate, and bromides. In 1903, 1 the use of barbituric acid and its derivatives was a significant advance in this field, until the accompanying hazards of addiction, overdosage, and toxicity became apparent. While barbiturates are still the most widely used medicaments, the search progressed with the use of anticonvulsants (especially hydantoin derivatives). Even antihistaminic agents play a lesser role as sedatives. Meparfynol has also been introduced as a sedative-hypnotic, but here one must be alert to the possibility of liver damage. In recent years, mephenesin 2 has entered the field. Partial success has been obtained with its use in certain anxiety states, 3 in certain neurological and muscular disorders, 4 and as an adjunct in alcoholism. The relative success of this preparation suggested

Excerpt More than 80 examples of lymphadenopathy occurring after anticonvulsant therapy have been recorded. Most of the hydantoin derivatives have been implicated as being responsible for this effe...

Aus den Esteramiden (I) wurden mit Chlorkohlensaureathylester (II) die Verbindungen (III) erhalten, aus denen durch thermische Cyclisierung bei 250°C die 2-(1-Hydantoin)-propionsaureester (IV) dargestellt wurden.

Die Thiohydantoine (I) und (IV) lassen sich mit BF3-Dimethylatherat in Toluol (Chlorbenzol) selektiv zu den S-Methylderivaten (II) bzw. (V) methylieren (Aus beuten 47-81%).

Beim Erhitzen des Gemisches aus Glykolsaurenitril (I) und Ammoniumbicarbonat mit Mineralsaure entsteht in 82%iger Ausbeute Hydantoin (II).

Beim Erhitzen von Cyclohexylessigsaure (I) mit den Benzolderivaten (II) in Gegenwart von Polyphosphorsaure entstehen die Cyclohexylacetophenone (III).

An attempt has been made to explain the mechanism of the reaction in which benzil has been allowed to react with urea in presence of alkali to give rise to 5 : 5-diphenylhydantoin.

In the (CsLOH)∞ layered structure (L = 5,5-dimethyl-4-oxoimidazolidine-2-thione) L acts as a polyhapting molecule bridging four different Cs+ ions; each cation displays an eightfold coordination involving four ligand molecules and three OH- groups. The hydroxo groups are triply bridging three cesium atoms.

Background: Hydantoin derivatives are very promising candidates to improve the efficacy of anticancer chemotherapy. Previously, we demonstrated that eight hydantoin derivatives inhibited the P-glycoprotein (ABCB1) efflux pump of mouse T-lymphoma cells, as well as acting synergistically with the anticancer drug doxorubicin. Materials and Methods: The activity of the hydantoin derivatives were investigated in another MDR cancer model, namely Colo 205/S sensitive and Colo 320/R resistant colon carcinoma cells respectively, having normal or overexpressed ABCB1 systems. Results: Among the hydantoin derivatives evaluated, BS-1, MN-3 and JH-63 were the most effective ABCB1 transporter inhibitors at the concentration of 4 mg/l on the Colo 320/R cells, compared to the positive control, verapamil. Conclusion: The derivatives did not induce apoptosis of Colo 320/R resistant colon carcinoma cells, indicating that these hydantoin compounds are potent efflux pump inhibitors (EPI) without affecting the signalling pathways that regulate apoptosis.

Six new polyamides (5a-f) containing p-phenylenediacrylic and hydantoin moieties in the main chain were prepared by direct polycondensation reaction of 4-phenylenediacrylic acid (3) with 6 different hydantoin derivatives (4a-f) using thionyl chloride and pyridine as condensing agents and N-methyl-2-pyrolidone as solvent. These new polymers (5a-f) were obtained in high yield and inherent viscosity between 0.35-0.55 dL/g. The resulting polyamides were characterized by elemental analysis, viscosity measurements, thermal gravimetric analysis (TGA and DTG), solubility test, and FT-IR and UV-vis spectroscopy. 4-Phenylenediacrylic acid (3) was prepared by the reaction of terephthal aldehyde (1) with malonic acid (2) in the presence of pyridine.

The hydantoin derivatives and analogues may, in sensitive patients, induce a syndrome which so closely mimics lymphosarcoma, both clinically and pathologically, that it leads to long and costly hospitalization. A case is reported of a patient under treatment with diphenylhydantoin sodium for grand mal epilepsy. She was admitted to hospital with fever, joint swellings, facial edema, generalized aches and pains, and adenopathy. A lymph node biopsy led to the diagnosis of lymphoblastic lymphosarcoma, and the patient was treated with nitrogen mustard. A continuing adverse clinical picture eventually prompted withdrawal of the diphenylhydantoin sodium. Gradual clinical improvement followed. Resumption of the drug by the patient after discharge from the hospital caused a recrudescence, and she was readmitted. After withdrawal of the diphenylhydantoin sodium, the symptoms again subsided.