95378-36-2

Usage

Uses

Used in Pharmaceutical Industry:
DIETHYL 5-HYDANTOYLPHOSPHONATE is used as a reagent in various organic synthesis reactions for the production of pharmaceuticals, due to its versatile reactivity and its role as a valuable building block.
Used in Agrochemical Industry:
DIETHYL 5-HYDANTOYLPHOSPHONATE is used as a reagent in the synthesis of agrochemicals, contributing to the development of effective and innovative products for agricultural applications.
Used in Fine Chemicals Production:
DIETHYL 5-HYDANTOYLPHOSPHONATE is used as a precursor in the synthesis of chiral organophosphorus compounds, which are important in the production of fine chemicals.
Used in Medicinal Chemistry Research:
DIETHYL 5-HYDANTOYLPHOSPHONATE is used as a research compound in medicinal chemistry, exploring its potential applications due to its structural resemblance to hydantoin-based anticonvulsant drugs.

InChI:InChI=1/C7H13N2O5P/c1-3-13-15(12,14-4-2)6-5(10)8-7(11)9-6/h6H,3-4H2,1-2H3,(H2,8,9,10,11)

Upstream product

• 173904-10-4 5-bromohydantoin 
• 122-52-1 triethyl phosphite 
• 79428-78-7 2-Amino-2-(diethoxyphosphoryl)essigsaeure-ethylester 
• 461-72-3 2,4-imidazolidinedione 

Downstream Products

• 31615-89-1 2-(2,5-dioxo-imidazolidin-4-ylidene)-propionic acid ethyl ester 
• 731-39-5 (2,5-dioxo-imidazolidin-4-ylidene)-phenyl-acetic acid ethyl ester 
• 135352-61-3 5-(1-Benzyl-piperidin-4-ylidene)-imidazolidine-2,4-dione 
• 67917-89-9 5-(2-oxo-2-phenyl-ethylidene)-imidazolidine-2,4-dione 
• 135352-59-9 5-[2,2,2-Trifluoro-1-phenyl-eth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 135352-52-2 5-[1-(2,4,6-Trimethoxy-phenyl)-meth-(E)-ylidene]-imidazolidine-2,4-dione 
• 137920-33-3 5-[1-(2,3,4-Trimethoxy-6-nitro-phenyl)-meth-(E)-ylidene]-imidazolidine-2,4-dione 
• 137920-34-4 5-[1-(2,3,4-Trimethoxy-6-nitro-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 66872-77-3 5-Cyclohexylidene-imidazolidine-2,4-dione 
• 58117-83-2 5-phenethylidene-imidazolidine-2,4-dione 
• 137920-45-7 5-[1-(2,6-Dichloro-phenyl)-meth-(E)-ylidene]-imidazolidine-2,4-dione 
• 137920-46-8 5-[1-(2,6-Dichloro-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 3775-01-7 5-benzylidenehydantoin 
• 90771-20-3 (Z)-5-(2-hydroxybenzylidene)imidazolidine-2,4-dione 

Relevant academic research and scientific papers

Identification of the hydantoin alkaloids parazoanthines as novel CXCR4 antagonists by computational and in vitro functional characterization

CXCR4 chemokine receptor represents an attractive pharmacological target due to its key role in cancer metastasis and inflammatory diseases. Starting from our previously-developed pharmacophoric model, we applied a combined computational and experimental approach that led to the identification of the hydantoin alkaloids parazoanthines, isolated from the Mediterranean Sea anemone Parazoanthus axinellae, as novel CXCR4 antagonists. Parazoanthine analogues were then synthesized to evaluate the contribution of functional groups to the overall activity. Within the panel of synthesized natural and non-natural parazoanthines, parazoanthine-B was identified as the most potent CXCR4 antagonist with an IC50 value of 9.3 nM, even though all the investigated compounds were able to antagonize in vitro the down-stream effects of CXC12, albeit with variable potency and efficacy. The results of our study strongly support this class of small molecules as potent CXCR4 antagonists in tumoral pathologies characterized by an overexpression of this receptor. Furthermore, their structure–activity relationships allowed the optimization of our pharmacophoric model, useful for large-scale in silico screening.

Synthesis of parazoanthine B and analogs

A versatile synthesis of the natural product parazoanthine B (2) and its analogs, parazoanthine C (3) and 18-deoxy-parazoanthine B (4), has been accomplished by a key coupling reaction between a hydantoinic compound and an α-bromo-acetophenone derivative. The synthetic approach is designed to address preparation of a wider group of parazoanthine B analogs characterized by the presence of the 5,6-double bond of Z-configuration.

Synthesis and reactivity of 5-methylenehydantoins

5-Methylenehydantoin, as well as the N-mono- and N,N-di-protected derivatives, can be obtained by different synthetic routes. These compounds can undergo a large variety of reactions, such as Diels-Alder, epoxidation, methanol addition and conjugate addition reactions of different types of nucleophiles, including carbon (cyanide), nitrogen (piperidine) and sulfur (thiols, thioacetate) nucleophiles. The reactivity with electrophilic reagents, such as m-CPBA or methanol in acidic medium, and the need for Lewis acids to promote the conjugate addition reactions indicate that hydantoin is a poor electron-withdrawing group.

Practical enantioselective synthesis of a 3-aryl-3-trifluoromethyl-2- aminopropanol derivative

Development of a large-scale enantioselective synthesis of a lead compound containing a 3-aryl-3-trifluoromethyl-2-aminopropanol core is described. A single isomer of 3,3-disubstituted acrylic acid derivative was prepared via Perkin condensation or Horner

The use of Lewis acids in the synthesis of 5-arylhydantoins

Different Lewis acids are able to promote the Friedel-Crafts reaction between 5-bromohydantoin and aromatic compounds. In the case of phenol, mixtures of ortho and para isomers are always obtained, with Mg(ClO4) 2 leading to the best selectivity. However, the best overall yield of 5-(hydroxyphenyl)hydantoin is obtained with YbCl3. This method can be extended to other aromatic systems such as anisole and thiophene. These reactions give similar yields but proceed with total selectivity to 5-(4-methoxyphenyl)hydantoin and 5-(2-thiophenyl)hydantoin, respectively. The cationic exchange of MgII and YbIII on anionic solid supports allows the preparation of very efficient heterogeneous catalysts for this reaction (productivity up to 600 mol of hydantoin per mole of Mg). These catalysts have practical advantages in that they can be recycled and reused.

Diethyl 2,4-Dioxoimidazolidine-5-phosphonates: Horner-Wadsworth-Emmons Reagents for the Mild and Efficient Preparation of C-5 Unsaturated Hydantoin Derivatives

The phosphonates 19 and 20 were prepared from hydantoin and 1-methylhydantoin, respectively, by way of bromination at C-5 and a subsequent Michaelis-Arbuzov reaction with triethyl phosphite.The Horner-Wadsworth-Emmons-type reagents 19 and 20 were found to react readily with aromatic and aliphatic aldehydes, in the presence of a base, to produce C-5 unsaturated hydantoin derivatives 22 and 26, generally in high yield.The products 22 and 26 were frequently isolated as mixtures of E and Z isomers depending upon the identity of the aldehyde and phosphonate.The isomeric configuration of the products was determined from analysis of NMR spectral data.Long-range (13)C-(1)H coupling constants between the C-4 carbonyl of the hydantoin ring and the olefinic proton were found to be diagnostic of isomer geometry.Conditions were also developed that allowed coupling of 19 and 20 with cyclic and acyclic ketones and α-dicarbonyl compounds to afford the corresponding olefinic products.C-5 unsaturated hydantoin derivatives are of synthetic utility as precursors to α-amino acid derivatives, pyruvates, and the imidazoquinolin-2-one heterocyclic ring system, a class of potent inhibitors of low Km cAMP phosphodiesterase and the chromophore present in the siderophore azotobactin.

Imidazoquinoline antithrombrogenic cardiotonic agents

Novel series of 1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-ones of the Formula STR1 wherein R1 is halogen, lower alkyl, lower alkoxy, trifluoromethyl; R2 is hydrogen, halogen, lower alkyl, lower alkoxy; R3 is hydrogen, haloge