2301-40-8

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Imidazolidinedione, 3-(phenylmethyl)is used as an anticonvulsant for the treatment of various types of seizures, such as complex partial seizures and generalized tonic-clonic seizures. It is also utilized to prevent seizures during or after surgery on the nervous system.
Used in Medical Treatments:
Phenytoin is employed as a medication to manage seizures, ensuring that patients maintain a controlled and stable condition. It is crucial for patients to adhere to their doctor's instructions and undergo regular monitoring while taking this medication to guarantee its safety and effectiveness.
Common side effects associated with the use of 2,4-Imidazolidinedione, 3-(phenylmethyl)include dizziness, drowsiness, slurred speech, and headaches. However, it is also important to be aware of the potential for more serious side effects, such as the rare but severe skin reaction known as Stevens-Johnson syndrome.

Upstream product

• 461-72-3 2,4-imidazolidinedione 
• 100-39-0 benzyl bromide 
• 3173-56-6 benzyl isothiocyanate 
• 100-44-7 benzyl chloride 
• 1128079-90-2 tert-butyl-3-benzyl-2,4-dioxoimidazolidine-1-carboxylate 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 22003-17-4 O-phenyl N-benzylcarbamate 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 25370-09-6 dibenzylcarbamyl chloride 
• 23583-12-2 N-benzyl-2-(3-benzylureido)acetamide 

Downstream Products

• 143582-10-9 3-Benzyl-5-[1-p-tolyl-meth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 143582-07-4 3-Benzyl-5-[1-(4-fluoro-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 143582-09-6 3-Benzyl-5-[1-(4-methoxy-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 143582-08-5 3-benzyl-5-(2,4-dichlorobenzylidene)imidazolidine-2,4-dione 
• 149437-10-5 3-Benzyl-5-[1-(4-bromo-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 143582-05-2 3-benzyl-5-(2-fluorobenzylidene)imidalizolidine-2,4-dione 
• 143582-11-0 3-Benzyl-5-[1-m-tolyl-meth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 56904-09-7 N-methyl-2-(benzylamino)ethylamine 
• 85369-80-8 3-benzyl-4-hydroxy-imidazolidin-2-one 
• 67909-04-0 1-benzyl-1,3-dihydro-2H-imidazol-2-one 
• 197504-84-0 3-benzyl-4-thioxo-imidazolidin-2-one 
• 123944-80-9 3-Benzyl-1-(4-nitrobenzyl)imidazolidin-2,4-dione 
• 941299-76-9 5-[(Z)-(1-benzyl-2,5-dioxoimidazolidin-4-ylidene)methyl]-2-hydroxybenzoic acid 
• 1035587-74-6 3-benzyl-1-(chlorosulfonyl)imidazolidine-2,4-dione 

Relevant academic research and scientific papers

One-Pot Oxidation of Secondary Alcohols to α-Hydroxy Ketones: Application to Synthesis of Oxoaplysinopsin D, E, F, & G

A simple one-pot transformation of secondary alcohols to α-hydroxy ketones using pyridinium dichromate (PDC) in DMF has been developed and substrate scope tested with 25 compounds of hydantoin derivatives. Using this method, we have devised a common dihyd

Chemoselective Electrosynthesis Using Rapid Alternating Polarity

Challenges in the selective manipulation of functional groups (chemoselectivity) in organic synthesis have historically been overcome either by using reagents/catalysts that tunably interact with a substrate or through modification to shield undesired sites of reactivity (protecting groups). Although electrochemistry offers precise redox control to achieve unique chemoselectivity, this approach often becomes challenging in the presence of multiple redox-active functionalities. Historically, electrosynthesis has been performed almost solely by using direct current (DC). In contrast, applying alternating current (AC) has been known to change reaction outcomes considerably on an analytical scale but has rarely been strategically exploited for use in complex preparative organic synthesis. Here we show how a square waveform employed to deliver electric current - rapid alternating polarity (rAP) - enables control over reaction outcomes in the chemoselective reduction of carbonyl compounds, one of the most widely used reaction manifolds. The reactivity observed cannot be recapitulated using DC electrolysis or chemical reagents. The synthetic value brought by this new method for controlling chemoselectivity is vividly demonstrated in the context of classical reactivity problems such as chiral auxiliary removal and cutting-edge medicinal chemistry topics such as the synthesis of PROTACs.

Design, synthesis and biological evaluation of novel 5-((substituted quinolin-3-yl/1-naphthyl) methylene)-3-substituted imidazolidin-2,4-dione as HIV-1 fusion inhibitors

A series of novel 5-(substituted quinolin-3-yl or 1-naphthyl)methylene)-3-substituted imidazolidin-2,4-dione 9–26 was designed and synthesized. The prepared compounds were identified using 1H NMR, 13C NMR as well as elemental analyses. The inhibitory activity of 9–26 on HIV-1IIIB replication in MT-2 cells was evaluated. Some derivatives showed good to excellent anti-HIV activities as compounds 13, 18, 19, 20, 22 and 23. They showed EC50 of 0.148, 0.460, 0.332, 0.50, 0.271 and 0.420 μM respectively being more potent than compound I (EC50 = 0.70 μM) and II ( EC50 = 2.40 μM) as standards. The inhibitory activity of 9–26 on infected primary HIV-1 domain, 92US657 (clade B, R5) was investigated. All the tested compounds consistently inhibited infection of this virus with EC50 from 0.520 to 11.857 μM. Results from SAR studies showed that substitution on ring A with 6/7/8-methyl group resulted in significant increase in the inhibitory activity against HIV-1IIIB infection (5- >300 times) compared to the unsubstituted analog 9. The cytotoxicity of these compounds on MT-2 cells was tested and their CC50 values ranged from 11 to 85 μM with selectivity indexes ranged from 0.53 to 166. The docking study revealed nice fitting of the new compounds into the hydrophobic pocket of HIV-1 gp41 and higher affinity than NB-64. Compound 13, the most active in preventing HIV-1IIIB infection, adopted a similar orientation to compound IV. Molecular docking analysis of the new compounds revealed hydrogen bonding interactions between the imidazolidine-2,4-dione ring and LYS574 which were missed in the weakly active derivatives.

Design, synthesis and biological evaluation of imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as lymphoid-specific tyrosine phosphatase inhibitors

Lymphoid-specific tyrosine phosphatase (LYP), which exclusively exists in immune cells and down-regulates T cell receptor signaling (TCR), has becoming a potent target for various autoimmune diseases. Herein, we designed and synthesized imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as new LYP inhibitors. Among them, the cinnamic acids-based inhibitors (9p and 9r) displayed good LYP inhibitory activities (IC50 = 2.85–6.95 μM). Especially, the most potent inhibitor 9r was identified as competitive inhibitor (Ki = 1.09 μM) and bind LYP reversibly. Meanwhile, 9r exhibited better selectivity over other phosphatases than known LYP inhibitor A15. Furthermore, compound 9r could regulate TCR associated signaling pathway in Jurkat T cell.

HETEROCYCLIC INTEGRIN AGONISTS

The present invention provides polycyclic oxothioxoimidazolidines, dioxoimidazolines, oxothioxooxazolidines, dioxooxazolidines, and related compounds, which are useful as integrin agonists. Methods for the treatment of integrin-mediated diseases such as cancer are also described.

2,4-Imidazolinedione heterocyclic derivative, and preparation method and use thereof

The invention belongs to the field of chemical medicines, and concretely relates to a 2,4-imidazolinedione heterocyclic derivative, and a preparation method and a use thereof. The structure of the 2,4-imidazolinedione heterocyclic derivative is represented by formula I. The invention also provides the preparation method and the use of the 2,4-imidazolinedione heterocyclic derivative. The 2,4-imidazolinedione heterocyclic derivative has a good inhibition effect on Pim-1 protein kinase micro-molecules, and has important exploitation application prospect.

Facile One-Pot Synthesis of Substituted Hydantoins from Carbamates

A novel and simple approach for the preparation of 3-substituted, 5-substituted, or 3,5-disubstituted hydantoins is reported. It involves the reaction of α-amino methyl ester hydrochlorides with carbamates to yield the corresponding ureido derivatives, which subsequently cyclize under basic conditions to produce substituted hydantoins in good yields. By applying this method, the bioactive anticonvulsant drug ethotoin was synthesized in good yield. The process avoids conventional multistep protocols and does not use the hazardous, irritant, toxic, or moisture-sensitive reagents, such as isocyanates or chloroformates, that are commonly used for the synthesis of these important compounds.

Structural exploration, synthesis and pharmacological evaluation of novel 5-benzylidenethiazolidine-2,4-dione derivatives as iNOS inhibitors against inflammatory diseases

In our previous work, 3I inhibited the LPS-induced iNOS activity and NO production in RAW 264.7 cells and improved joint inflammation and cartilage destruction in inflammatory model. In this study, we synthesized 59 derivatives and bioisosteres on the bas

Synthesis of hydantoins and dihydrouracils via thermally-promoted cyclization of ureidoacetamides

The synthesis of hydantoins and dihydrouracils from ureidoacetamides has been carried out at high temperature in glycol solvents. A series of substrates were prepared and examined to determine the effect of substrate structure, N-acyl substitution (X), and solvent on the course of the reaction. A dramatic effect was observed when using ureidoacetamides (e.g., X=N-methyl-N-phenyl), which led to higher yields, faster reaction times, and lower racemization of chiral substrates. The rate of racemization of a chiral hydantoin in the presence of dibenzylamine and N-methyl aniline has also been determined. The thermal cyclization methodology has been applied to the preparation of a complex hydantoin.

De novo fragment design: A medicinal chemistry approach to fragment-based lead generation

The use of fragments with low binding affinity for their targets as starting points has received much attention recently. Screening of fragment libraries has been the most common method to find attractive starting points. Herein, we describe a unique, alt