21083-47-6Relevant academic research and scientific papers
Anti-proliferation effect of 5,5-diphenyl-2-thiohydantoin (DPTH) in human vascular endothelial cells
Shin, Chun-Ru,Wu, Jender,Liu, Yuan,Liang, Yu-Chih,Lin, Shyr-Yi,Sheu, Ming-Thau,Lee, Wen-Sen
, p. 67 - 76 (2004)
The aim of this study was to examine the anti-proliferation effect of 5,5-diphenyl-2-thiohydantoin (DPTH), an analogue of antiepileptic drug phenytoin (5,5-diphenylhydantoin), on human umbilical vein endothelial cells (HUVEC) and its possible molecular mechanism underlying. Here we demonstrated that DPTH at a range of concentrations (12.5-50 μM) dose- and time-dependently inhibited DNA synthesis and decreased cell number in cultured HUVEC, but not human fibroblasts. DPTH was not cytotoxic at these concentrations. [3H]Thymidine incorporation and flow cytometry analyses demonstrated that treatment of HUVEC with DPTH arrested the cell at the G0/G1 phase of the cell cycle. Western blot analysis revealed that the protein level of p21 increased after DPTH treated. In contrast, the protein levels of p27, p53, cyclins A, D1, D3 and E, cyclin-dependent kinase (CDK)2, and CDK4 in HUVEC were not changed significantly after DPTH treatment. Immunoprecipitation showed that the formations of the CDK2-p21 and CDK4-p21 complex, but not the CDK2-p27 and CDK4-p27 complex, were increased in the DPTH-treated HUVEC. Kinase assay further demonstrated that both CDK2 and CDK4 kinase activities were decreased in the DPTH-treated HUVEC. Pretreatment of HUVEC with a p21 antisense oligonucleotide reversed the DPTH-induced inhibition of [3H]thymidine incorporation into HUVEC. In conclusion, these data suggest that DPTH inhibits HUVEC proliferation by increasing the level of p21 protein, which in turn inhibits CDK2 and CDK4 kinase activities, and finally interrupts the cell cycle. The findings from the present study suggest that DPTH might have the potential to inhibit the occurrence of angiogenesis.
Facile access to polymer supported zinc–salen complex: highly efficient heterogeneous catalyst for synthesizing hydantoins, thiohydantoins and Schiff bases in aqueous medium
Balinge, Kamlesh Rudreshwar,Khiratkar, Avinash Ganesh,Muskawar, Prashant Narayan,Thenmozhi,Bhagat, Pundlik Rambhau
, p. 2075 - 2097 (2017/12/26)
The synthesis of polymer supported zinc–salen complex (PS-Zn–salen) is described. The mononuclear zinc(II)–salen complex was characterized by Fourier-transform NMR spectroscopy, energy-dispersive X-ray spectroscopy, Fourier transform infrared spectrophotometry (FT-IR), thermogravimetric analysis, scanning electron microscopy, surface area and pore size distribution by Brunauer–Emmett–Teller. The synthesized PS-Zn–salen complex used as a recyclable heterogeneous catalyst for the efficient synthesis of hydantoins, thiohydantoins and Schiff bases in an aqueous medium. The isolated yields of hydantoins, thiohydantoins and Schiff bases achieved up to 89, 95 and 94%, respectively. In spite of conventional heterogeneous catalysts, current PS-Zn–salen complex shows thermal stability up to 280?°C. Moreover, the catalyst could be recovered easily by simple filtration and reused for next run with slightly declining its activity up to six successive runs. The FT-IR spectrum of recycle catalyst after 6th run confirmed that the catalyst was stable during the course of a reaction. The leaching of metal from the PS-Zn–salen is negligible, which was confirmed by AAS and hot filtration test.
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
One-step liquid-phase heterogeneous synthesis of phenytoin using modified calcium oxide as a solid basic catalyst
Tang, Ying,Cheng, Qitong,Wang, Shanshan,Zhang, Jie
, p. 1501 - 1506 (2014/11/08)
A highly efficient heterogeneous method for the synthesis of phenytoin from benzil and urea has been established by using modified CaO as a solid basic catalyst. A relatively high yield of phenytoin was obtained (60.5 %) with a urea/benzil molar ratio of 2.5 at a reaction temperature of 40 °C in the presence of commercial CaO. The yield of phenytoin was greatly enhanced to 90.8 % after treatment of commercial CaO with benzyl bromide. The results of Fourier transform infrared spectroscopy and thermogravimetry analysis implied that the modifier was chemically bonded onto the surface of CaO and almost no Ca(OH) 2 was formed during the modification process. The effects of modification and reaction conditions on the yield as well as the possible mechanism were studied thoroughly. Graphical abstract: [Figure not available: see fulltext.]
Microwave-assisted solid-phase synthesis of 4,5-dihydroxy-1,3-dialkyl-4,5- diarylimidazolidine-2-thione and thiohydantoins
Ghanbari, Mohammad M.,Mahdavinia, Gholam H.,Safari, Javad,Naeimi, Hossein,Zare, Mehdi
experimental part, p. 2414 - 2420 (2011/08/05)
4,5-Dihydroxy-1,3-dialkyl-4,5-diarylimidazolidine-2-thione are obtained in good yields from the 1:1 addition reaction between benzil derivatives and thiourea derivatives in the solid phase. These compounds undergo smooth rearrangement followed by a hydrogen shift to produce thiohydantoins in excellent yields.
Synthesis characterization and biological evaluation of some alkoxyphthalimide derivatives of 3-(4-substituted phenyl)-6, 6-diphenyl-3,3a-dihydro-2H-imidazo[2,1-b]pyrazolo[3,4-d] [1,3]thiazol-7(6H)-one
Dangi, Raja Ram,Hussain, Nasir,Talesara, Ganpat Lal
experimental part, p. 1490 - 1498 (2012/06/15)
A series of 2-N-ethoxyphthalimido 3-(4-substitutedphenyl)- 6,6-diphenyl-3,3a-dihydro-2H-imidazo[2,1-b] pyrazolo[3,4-d][1,3]thiazol-7(6H)- one(7a-e) and 4-(4-substituted phenyl)-2-(N-ethoxyphthalimido amino)-7,7-diphenylimidazo[ 2',1':2,3][1,3]thiazolo[4,5-d] pyrimidin-8(7H)-one (9a-e) have been designed and synthesized starting from thiohydentoin (1). The structure of all synthesized compounds has been established by IR, 1H NMR, 13C NMR and mass studies. These compounds have been screened for antimicrobial activities in order to evaluate the possibility of the derivatives to be used as potential chemotherapeutic agents. Springer Science+Business Media, LLC 2010.
Synthesis of hydantoins, thiohydantoins, and glycocyamidines under solvent-free conditions
Hashmi, Imran Ali,Aslam, Afshan,Ali, Syed Kashif,Ahmed, Viqar-Uddin,Ali, Firdous Imran
experimental part, p. 2869 - 2874 (2010/11/05)
Hydantoins, thiohydantoins, and glycocyamidines have been prepared in moderate to excellent yields at room temperature under solvent-free conditions. 3N-amino and carboamide derivatives of hydantoin (7-8) were prepared in single step by condensing benzil with semicarbazide and biuret respectively.
Substituted 2-thioxoimidazolidin-4-ones and imidazolidine-2,4-diones as fatty acid amide hydrolase inhibitors templates
Muccioli, Giulio G.,Fazio, Nicola,Scriba, Gerhard K. E.,Poppitz, Wolfgang,Cannata, Fabio,Poupaert, Jacques H.,Wouters, Johan,Lambert, Didier M.
, p. 417 - 425 (2007/10/03)
The demonstration of the essential role of fatty acid amide hydrolase (FAAH) in hydrolyzing endogenous bioactive fatty acid derivatives has launched the quest for the discovery of inhibitors for this enzyme. Along this line, a set of 58 imidazolidine-2,4-dione and 2-thioxoimidazolidin-4-one derivatives was evaluated as FAAH inhibitors. Among these compounds, 3-substituted 5,5′-diphenylimidazolidine-2,4-dione and 3-substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one derivatives were previously described as CB1 cannabinoid receptor ligands. In the present study, we synthesized several derivatives exhibiting interesting FAAH inhibitory activity and devoid of affinity for the CB1 and CB2 cannabinoid receptors. For instance, 3-heptyl-5,5′-diphenylimidazolidine- 2,4-dione (14) and 5,5′-diphenyl-3-tetradecyl-2-thioxo-imidazolidin-4-one (46) showed p/50 values of 5.12 and 5.94, respectively. In conclusion, it appears that even though several 3-substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one and 3-substituted 5,5′-diphenylimidazolidine-2,4-dione derivatives have been previously shown to behave as CB1 cannabinoid receptor ligands, appropriate substitutions of these templates can result in FAAH inhibitors devoid of affinity for the cannabinoid receptors.
A rapid and efficient microwave-assisted synthesis of hydantoins and thiohydantoins
Muccioli, Giulio G.,Poupaert, Jacques H.,Wouters, Johan,Norberg, Bernadette,Poppitz, Wolfgang,Scriba, Gerhard K.E.,Lambert, Didier M.
, p. 1301 - 1307 (2007/10/03)
The present paper describes studies on the synthesis of the antiepileptic drug phenytoin, and of structurally related derivatives. First, the influence of the solvent has been investigated in the microwave-assisted synthesis of the drug, resulting in a yield improvement and a cleaner reaction. Second, a two-step reaction is described to synthesize selectively and in high yields phenytoin. The first step consists in microwave activation of the reaction of benzil with thiourea, the second step includes the conversion of the resulting 2-thiohydantoin to phenytoin using hydrogen peroxide. Moreover, microwave activation is a very convenient method for the synthesis of 3-alkylated phenytoin derivatives, resulting in a much more selective method than the previously reported procedure using alkylating agents.
Mechanistic Studies in the Chemistry of Thiourea. Part 1. Reaction with Benzil Under Alkaline Conditions
Broan, Christopher J.,Butler, Anthony R.,Reed, David,Sadler, Ian H.
, p. 731 - 740 (2007/10/02)
Benzil reacts under alkaline conditions with 1,3-dimethylthiourea to form 4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione (1); with 1-methylthiourea to form 3-methyl-5,5-diphenyl-2-thiohydantoin (9); and with thiourea to form both the corresponding hydantoin and 3a,7a-diphenyltetrahydroimidazoimidazole-2,5-dithione (19).The use of high field n. m. r. spectroscopy and benzil labelled with carbon-13 in the carbonyl group has permitted delineation of the reaction mechanisms and detection of a number of transient intermediates.
