ChemInform Abstract: Racemates and Enantiomers of Basic Substituted 5‐Phenylhydantoins. Syntheses and Antiarrhythmic Activity.

Knabe, J.; Baldauf, J.; Ahlhelm, A.

doi:10.1002/chin.199812100

Cited by 9 publications

(10 citation statements)

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“…Hydantoins (imidazolidine-2,4-diones), having a 5-membered ring containing a reactive cyclic urea core, form a wide range of biologically active compounds [1][2][3][4] . Their 2-thioxo analogs, 2-thiohydantoins (2-thioxo-imidazolizin-4-one) also display significant biological activities and are employed as established drugs, fungicides or herbicides [5,6] .…”

Section: Introductionmentioning

confidence: 99%

Crystal Structures and Conformations of 5-Benzyl-2-thiohydantoin and Its 1-Acetylated Derivative

Kunimoto

Ichitani

Ogawa

et al. 2009

Spectroscopy Letters

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Abstract:The crystal structures of 5-benzyl-2-thiohydantoin (5-BTH) and 1-acetyl-5-benzyl-2-thiohydantoin (1-Ac-5-BTH) have been determined by X-ray diffraction. In the 5-BTH crystals, the enantiomeric (R)-and (S)-5-BTH molecules are connected to form cyclic dimers via the hydrogen bonds of the thioamide and the amide moieties. On the other hand, the intermolecular hydrogen bonds in 1-Ac-5-BTH crystals form an infinite chain. These differences 1 SpectroscLett_kunimoto_revised in the hydrogen bond pattern are also discussed in the IR and Raman spectra. The ab initio molecular orbital calculations (Gaussian 03) with 6-31G(d,p) basis set were carried out for 5-BTH and 1-Ac-5-BTH to get the preferred conformation.

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Section: Introductionmentioning

confidence: 99%

Crystal Structures and Conformations of 5-Benzyl-2-thiohydantoin and Its 1-Acetylated Derivative

Kunimoto

Ichitani

Ogawa

et al. 2009

Spectroscopy Letters

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“…Hydantoins are a well known class of antiepileptic drugs used in the treatment of epilepsy [1][2][3][4]. It is recognized that they bind to the neuronal voltage-gated sodium channel (NVSC) protein, eliciting its pharmacological effects by prolonging the channel's bioelectrically inactive state.…”

Section: Introductionmentioning

confidence: 99%

Structure-Retention Relationship Study of HPLC Data of Antiepileptic Hydantoin Analogues

Djaković‐Sekulić¹,

Mandić²,

Trišović³

et al. 2012

CAD

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In the study, 18 antiepileptic hydantoin analogues were investigated by means of reversed-phase HPLC on C-18 stationary phase and eluent acetonitrile-water. Quantitative structure-retention relationship (QSRR) study has been applied in order to understand factors that affect the retention which is closely correlated to the activity (ED₅₀ values). To overview the compounds for similarities and dissimilarities principal component analysis (PCA) has been applied. Six multiple linear regression models based on the most relevant descriptors were developed. Descriptors for MLR were selected according to variable importance calculated by partial least squares (PLS) analysis. Besides ALOGP the most important is aromatic ratio for mobile phases with more than 45% of acetonitrile, as well as electrotopological states when the % of acetonitrile is less than 40%. High agreement between experimental and predicted retention, obtained in the validation procedure, indicated the good quality of the derived QSRR models. For individual linear models, crossvalidation squared correlation coefficients (Q²) ranging from 0.697 to 0.837 were obtained. The residual values (difference between observed and calculated) agreed well within experimental error. Additionally, models were compared in terms of the smallest residual value by recently developed method of ranking based on the sum of ranking differences (SRD).

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“…Besides being anticonvulsants, various other activities of hydantoin's derivative have been reported in literature, such as antiarrhytmics, antimicrobial, antifungal, or antitumor activity [5][6][7][8]. Mephenytoin was introduced approximately 10 years after Phenytoin in the late 1940s.…”

Section: Introductionmentioning

confidence: 99%

“…Although no longer available as a drug, Mephenytoin and its metabolites are still studied largely because of their interesting hydroxylation polymorphism. Besides being anticonvulsants, various other activities of hydantoin's derivative have been reported in literature, such as antiarrhytmics, antimicrobial, antifungal, or antitumor activity [5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Multivariate evaluation of the correlation between retention data and molecular descriptors of antiepileptic hydantoin analogs

Djaković‐Sekulić

Smoliński

Trišović³

et al. 2012

Journal of Chemometrics

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Molecular properties relevant to pharmacokinetics of two sets of newly synthesized hydantoin derivatives based on two well-known drugs (Nirvanol and Phenytoin) were studied. Properties under consideration were either determined empirically by reversed-phase high-performance thin-layer chromatography or calculated by the use of established theoretical medicinal chemistry/drug design software. These properties represent selected structural features of analytes, which affect their processes of absorption, distribution, metabolism, excretion, and toxicity. Principal component analysis was used to visualize the differences between six mobile phase modifiers used as well as similarities between 24 analyzed compounds. To find appropriate quantitative relationships between R M, W for the tested compounds and molecular descriptors, stepwise regression, partial least squares (PLS), and robust PLS were used. The best results were obtained with robust PLS.

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ChemInform Abstract: Racemates and Enantiomers of Basic Substituted 5‐Phenylhydantoins. Syntheses and Antiarrhythmic Activity.

Cited by 9 publications

References 0 publications

Crystal Structures and Conformations of 5-Benzyl-2-thiohydantoin and Its 1-Acetylated Derivative

Crystal Structures and Conformations of 5-Benzyl-2-thiohydantoin and Its 1-Acetylated Derivative

Structure-Retention Relationship Study of HPLC Data of Antiepileptic Hydantoin Analogues

Multivariate evaluation of the correlation between retention data and molecular descriptors of antiepileptic hydantoin analogs

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