4224-00-4Relevant articles and documents
New aspects of reactions of methyl (thio)ureas with benzil
Baranov, Vladimir V.,Kravchenko, Angelina N.,Nelyubina, Yulia V.,Vol'khina, Tatyana N.
, p. 673 - 676 (2021/11/26)
New pathways of reaction between 1-methylthiourea or 1-methylurea and benzil bring about new derivatives of (2S*,3aR*,6aS*)-perhydro-3aH-[1,3]dioxolo[4,5-d]imidazole and racemic (4S*,5R*)-4-alkoxy-5-hydroxy-1-methyl-4,5-diphenylimidazolidine-2-thiones. So
Direct N1-selective alkylation of hydantoins using potassium bases
Shintani, Yumi,Kato, Koichi,Kawami, Masashi,Takano, Mikihisa,Kumamoto, Takuya
, p. 407 - 410 (2021/04/30)
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
Chitosan decorated Fe3O4 nanoparticles as a magnetic catalyst in the synthesis of phenytoin derivatives
Safari, Javad,Javadian, Leila
, p. 48973 - 48979 (2014/12/11)
In the present work, Fe3O4 nanoparticles were synthesized by the chemical coprecipitation process. Subsequently, the synthesized nanoparticles were modified with chitosan by a simple method and characterized by X-ray diffractometry (XRD), Fourier transform infrared spectrophotometry (FT-IR), vibrating sample magnetometry (VSM), scanning electron microscopy (SEM) and energy-dispersive X-ray spectroscopy (EDX). Then, phenytoin derivatives were catalyzed by magnetic Fe3O4-chitosan nanoparticles. Fe3O4-chitosan nanoparticles were found to be a recoverable organocatalyst for the efficient synthesis of 5,5-diphenylhydantoins and 5,5-diphenyl-2-thiohydantoins from substituted benzils and urea or thiourea derivatives. The nanocatalyst could be recovered easily under a magnetic field for reuse, and considerable loss of its catalytic activity was not observed after reuse in seven consecutive runs. This journal is
SAR-studies on the importance of aromatic ring topologies in search for selective 5-HT7 receptor ligands among phenylpiperazine hydantoin derivatives
Handzlik, Jadwiga,Bojarski, Andrzej J.,Sata?a, Grzegorz,Kubacka, Monika,Sadek, Bassem,Ashoor, Abrar,Siwek, Agata,Wi?cek, Ma?gorzata,Kucwaj, Katarzyna,Filipek, Barbara,Kie?-Kononowicz, Katarzyna
, p. 324 - 339 (2014/04/17)
The current study is focused on newly developed phenylpiperazine derivatives of aromatic methylhydantoin differing in mutual positions of methyl and phenyl moieties. The new compounds were synthesized using Bucherer-Bergs reaction, two-phase alkylation, Mitsunobu reaction and/or an alkylation under microwave irradiation. The compounds developed were assessed on their affinity for serotoninergic receptors 5-HT1A, 5-HT6, 5-HT 7 and α1-ARs in radioligand binding assays. Selected compounds were tested on their inhibitory effect at human 5-HT3A expressed in Xenopus Oocytes as well as on their activity at α1-adrenoceptor subtypes in functional and electrophysiological bioassays, respectively. Most of investigated compounds exhibited affinities for α1-ARs, 5-HT1A, 5-HT7 (Ki ～ 0.8-353 nM) significantly higher than those for 5-HT6 receptors. Very weak inhibitory effect at 5-HT3A accompanied with high activity at α1D-AR subtypes were observed for selected representative compounds. Among the current series, particularly 5-(4-fluorophenyl)-3-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl) -5-methylimidazolidine-2,4-dione hydrochloride (25a) displayed the highest 5-HT7 affinity with Ki = 3 nM and selectivity with 40-3600 fold towards 5-HT1A, 5-HT6, and α1-ARs.
Structure-activity relationships of 3-substituted-5,5-diphenylhydantoins as potential antiproliferative and antimicrobial agents
Trisovic, Nemanja,Bozic, Bojan,Obradovic, Ana,Stefanovic, Olgica,Markovic, Snezana,Comic, Ljiljana,Bozic, Biljana,Uscumlic, Gordana
scheme or table, p. 1597 - 1606 (2012/05/07)
A series of twelve 3-substituted-5,5-diphenylhydantoins was synthesized, including some whose anticonvulsant activities have already been reported in the literature. Their antiproliferative activities against HCT-116 human colon carcinoma cells were evalu
Solvent effects on the structure-activity relationship of phenytoin-like anticonvulsant drugs
Trisovic, Nemanja,Banjac, Nebojsa,Valentic, Natasa,Uscumlic, Gordana
body text, p. 199 - 208 (2009/10/09)
The absorption spectra of nine compounds structurally related to phenytoin (5,5-diphenylhydantoin) were recorded in twelve solvents over the range of 200 to 400 nm. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The lipophilic activity of the investigated hydantoins was estimated by calculation of their log 10 P values. The calculated values of log 10 P were correlated with the ratio of the contributions of specific and non-specific solute/solvent interactions. The correlation equations were combined with the corresponding ED50 values to generate new equations that demonstrate exact relationship between solute/solvent interactions and the structure-activity parameters.
Superacid Activated Condensation of Parabanic Acid and Derivatives with Arenes. A New Synthesis of Phenytoin and 5,5-Diarylhydantoins
Klumpp, Douglas A.,Yeung, Ka Yeun,Prakash, G. K. Surya,Olah, George A.
, p. 918 - 920 (2007/10/03)
A new synthetic route to phenytoin and 5,5-diarylhydantoins is repoted.Parabanic acid is converted to the 5,5-diarylhydantoins (65-98percent yield) from CF3SO3H and arenes.Deuterium substituted products are prepared in high yield from parabanic acid, CF3SO3D, and deuterated arenes.
