3775-01-7

Usage

Uses

Used in Pharmaceutical Industry:
5-Benzylidenehydantoin is used as a precursor in the synthesis of antiviral and antitumor medications. Its unique chemical structure allows it to be a key component in the development of life-saving drugs.
Used in Organic Chemical Reactions:
5-Benzylidenehydantoin is utilized as a reactive intermediate in the production of heterocyclic compounds. Its ability to participate in various organic reactions makes it a valuable asset in the synthesis of complex organic molecules.

InChI:InChI=1/C10H8N2O2/c13-9-8(11-10(14)12-9)6-7-4-2-1-3-5-7/h1-6H,(H2,11,12,13,14)/b8-6-

Upstream product

• 461-72-3 2,4-imidazolidinedione 
• 100-52-7 benzaldehyde 
• 57-13-6 urea 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 7647-01-0 hydrogenchloride 
• 145693-93-2 5-benzylidene-2-methylsulfanyl-3,5-dihydro-imidazol-4-one 
• 583-46-0 5-benzylidene-2-thiohydantoin 
• 52800-58-5 5-phenylmethylene-4-thioxo-2-imidazolidinone 
• 78-96-6 3-amino-2-propanol 
• 302-72-7 rac-Ala-OH 
• 109754-06-5 (E)-5-(benzylidene)imidazolidine-2,4-dione 
• 95474-44-5 (5Z)-5-benzylidene-2-thioxo-imidazolidin-4-one 
• 154198-91-1 (E)-2-Isocyanato-3-phenyl-acrylonitrile 
• 74805-43-9 (Z)-N-benzyloxycarbonyldehydrophenylalanine azide 

Downstream Products

• 100142-60-7 3-ethyl-5-benzylidene-imidazolidine-2,4-dione 
• 31113-72-1 N,N'-dimethyl-5-benzylidenehydantoin 
• 3530-82-3 5-benzyl-hydantoin 
• 117979-63-2 5-(p-chlorosulfonylbenzylidene)hydantoin 
• 89-24-7 5-phenylimidazolidine-2,4-dione 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 100-52-7 benzaldehyde 
• 331628-10-5 {4-[2,5-Dioxo-imidazolidin-(4Z)-ylidenemethyl]-benzenesulfonylamino}-acetic acid 
• 331628-13-8 3-{4-[2,5-Dioxo-imidazolidin-(4Z)-ylidenemethyl]-benzenesulfonylamino}-propionic acid 
• 331628-15-0 2-{4-[2,5-Dioxo-imidazolidin-(4Z)-ylidenemethyl]-benzenesulfonylamino}-3-methyl-butyric acid 
• 331628-17-2 2-{4-[2,5-Dioxo-imidazolidin-(4Z)-ylidenemethyl]-benzenesulfonylamino}-4-methyl-pentanoic acid 
• 117979-65-4 4-[2,5-Dioxo-imidazolidin-(4Z)-ylidenemethyl]-N,N-dimethyl-benzenesulfonamide 

Relevant academic research and scientific papers

Enantioselective Synthesis of Chiral Substituted 2,4-Diketoimidazolidines and 2,5-Diketopiperazines via Asymmetric Hydrogenation

An enantioselective hydrogenation of 5-alkylidene-2,4-diketoimidazolidines (hydantoins) and 3-alkylidene-2,5-ketopiperazines catalyzed by the Rh/f-spiroPhos complex under mild conditions has been developed, which provides an efficient approach to the highly enantioselective synthesis of chiral hydantoins and 2,5-ketopiperazine derivatives with high enantioselectivities up to 99.9% ee.

Sulfated and Oxygenated Imidazoline Derivatives: Synthesis, Antioxidant Activity and Light-Mediated Antibacterial Activity

Imidazoline derivatives with different exocyclic substituents were simply prepared from common starting materials. The procedures were carried out in an eco-friendly manner. The antioxidant activity of these derivatives was explored by different experimental assays, such as ABTS.+ and DPPH. scavenging assay, as well as reducing power assay. The structural differences are discussed in terms of the results. Sulfur analogs showed higher antioxidant activity than their oxygenated counterparts. The same tendency was observed in microbiological studies, in which the same imidazoline compounds were assayed for light-mediated activity against of Staphylococcus aureus and Escherichia coli strains. A light-enhanced activity was observed for almost all the sulfated imidazolines after exposure to UV-A (400-320 nm) light.

Discovery of novel UV-filters with favorable safety profiles in the 5-arylideneimidazolidine-2,4-dione derivatives group

Effective protection from the harmful effects of UV radiation may be achieved by using sunscreens containing organic or inorganic UV filters. The number of currently available UV filters is limited and some of the allowed molecules possess limitations such as systemic absorption, endocrine disruption properties, contact and photocontact allergy induction, and low photostability. In the search for new organic UV filters we designed and synthesized a series consisting of 5-benzylidene and 5-(3-phenylprop-2-en-1-ylidene)imidazolidine-2,4-dione (hydantoin) derivatives. The photoprotective activity of the tested compounds was confirmed in methanol solutions and macrogol formulations. The most promising compounds possessed similar UV protection parameter values as selected commercially available UV filters. The compound diethyl 2,20-((Z)-4-((E)-3-(4-methoxyphenyl)allylidene)-2,5-dioxoimidazolidine-1,3-diyl)diacetate (4g) was characterized as an especially efficient UVA photoprotective agent with a UVA PF of 6.83 ± 0.05 and favorable photostability. Diethyl 2,20-((Z)-4-(4-methoxybenzylidene)-2,5-dioxo-imidazolidine-1,3-diyl)diacetate (3b) was the most promising UVB-filter, with a SPFin vitro of 3.07 ± 0.04 and very good solubility and photostability. The main photodegradation products were geometric isomers of the parent compounds. These compounds were also shown to be non-cytotoxic at concentrations up to 50 μM when tested on three types of human skin cells and possess no estrogenic activity, according to the results of a MCF-7 breast cancer model.

Chemoenzymatic synthesis of L-3,4-dimethoxyphenyl-alanine and its analogues using aspartate aminotransferase as a key catalyst

In this study, a chemoenzymatic synthesis method for the production of L-3,4-dimethoxyphenyl-alanine and its analogues from phenylpyruvate derivatives was developed. The aspartate aminotransferase from Escherichia coli was engineered by error prone PCR and the improved variants were identified. When 3, 4-dimethoxy phenylpyruvate was added by fed-batch on a preparative scale, L-3,4-dimethoxyphenyl-alanine was formed in 95.4% conversion and > 99% ee with the best aspartate aminotransferase variant as the catalyst. This study provided an efficient method for the production of methoxy substituted phenylalanines using the engineered aspartate aminotransferase.

Evaluation of α-hydroxycinnamic acids as pyruvate carboxylase inhibitors

Through a structure-based drug design project (SBDD), potent small molecule inhibitors of pyruvate carboxylase (PC) have been discovered. A series of α-keto acids (7) and α-hydroxycinnamic acids (8) were prepared and evaluated for inhibition of PC in two assays. The two most potent inhibitors were 3,3′-(1,4-phenylene)bis[2-hydroxy-2-propenoic acid] (8u) and 2-hydroxy-3-(quinoline-2-yl)propenoic acid (8v) with IC50 values of 3.0 ± 1.0 μM and 4.3 ± 1.5 μM respectively. Compound 8v is a competitive inhibitor with respect to pyruvate (Ki = 0.74 μM) and a mixed-type inhibitor with respect to ATP, indicating that it targets the unique carboxyltransferase (CT) domain of PC. Furthermore, compound 8v does not significantly inhibit human carbonic anhydrase II, matrix metalloproteinase-2, malate dehydrogenase or lactate dehydrogenase.

Synthesis of chiral hydantoin derivatives by homogeneous Pd-catalyzed asymmetric hydrogenation

5-Aryl substituted chiral hydantoin derivatives were synthesized via asymmetric hydrogenation of prochiral exocyclic alkenes using a Pd/BINAP catalyst. Moderate to good enantioselectivity were obtained (21–90% ee). A chiral Br?nsted acid additive was foun

Identification of a New Zinc Binding Chemotype by Fragment Screening

The discovery of a new zinc binding chemotype from screening a nonbiased fragment library is reported. Using the orthogonal fragment screening methods of native state mass spectrometry and surface plasmon resonance a 3-unsubstituted 2,4-oxazolidinedione fragment was found to have low micromolar binding affinity to the zinc metalloenzyme carbonic anhydrase II (CA II). This affinity approached that of fragment sized primary benzenesulfonamides, the classical zinc binding group found in most CA II inhibitors. Protein X-ray crystallography established that 3-unsubstituted 2,4-oxazolidinediones bound to CA II via an interaction of the acidic ring nitrogen with the CA II active site zinc, as well as two hydrogen bonds between the oxazolidinedione ring oxygen and the CA II protein backbone. Furthermore, 3-unsubstituted 2,4-oxazolidinediones appear to be a viable starting point for the development of an alternative class of CA inhibitor, wherein the medicinal chemistry pedigree of primary sulfonamides has dominated for several decades.

Bioisosteric modification of known fucosidase inhibitors to discover a novel inhibitor of α-l-fucosidase

Bioisosteric modification of known fucosidase inhibitors A and B, resulted in three new types of molecules, 4b, 5c and 6a (belonging to furopyridinedione, thiohydantoin and hydantoin chemotypes) that could potentially bind to α-l-fucosidase (bovine kidney

Hydantoin-based molecular photoswitches

A new family of molecular photoswitches based on arylidenehydantoins is described together with their synthesis and photochemical and photophysical studies. A series of hydantoin derivatives have been prepared as single isomers using simple and versatile chemistry in good yields. Our studies show that the photostationary states of these compounds can be easily controlled by means of external factors, such as the light source or filters. Moreover, the detailed investigations proved that these switches are efficient (i.e., they make efficient use of the light energy, are high fatigue resistant, and are very photostable). In some cases, the switches can be completely turned on/off, a desirable feature for specific applications. A series of theoretical calculations have also been carried out to understand the photoisomerization mechanism at the molecular level.

SHIKIMATE PATHWAY INHIBITORS AND THE USE THEREOF

The present invention relates to methods of inhibiting shikimate pathway, comprising administering to a subject a pharmaceutically acceptable composition comprising a compound having a formula: or pharmaceutically acceptable salts thereof. The present invention also provides a synergistic antibacterial composition containing compound