120697-22-5

Upstream product

• 37428-88-9 5-(4-chloro-benzylidene)-2-thioxo-imidazolidin-4-one 
• 10040-86-5 (Z)-5-(4-chlorobenzylidene)imidazolidine-2,4-dione 
• 461-72-3 2,4-imidazolidinedione 
• 104-88-1 4-chlorobenzaldehyde 
• 95378-36-2 diethyl 2,4-dioxoimidazolidin-5-yl-phosphonate 
• 128256-89-3 5-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-3-[(methyl-phenyl-amino)-methyl]-2-methylsulfanyl-3,5-dihydro-imidazol-4-one 
• 128256-92-8 3-{4-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-5-oxo-4,5-dihydro-1H-imidazol-2-ylsulfanyl}-pentane-2,4-dione 
• 139488-42-9 3-Acetyl-5-[1-(4-chloro-phenyl)-meth-(Z)-ylidene]-2-thioxo-imidazolidin-4-one 
• 128256-80-4 5-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-3-[(methyl-phenyl-amino)-methyl]-2-thioxo-imidazolidin-4-one 

Downstream Products

• 10040-86-5 (Z)-5-(4-chlorobenzylidene)imidazolidine-2,4-dione 
• 6331-81-3 5-(4-chlorobenzyl)imidazolidine-2,4-dione 
• 6331-81-3 5-(4-chlorobenzyl)imidazolidine-2,4-dione 
• 937050-04-9 C₁₆H₂₀ClN₃O₃ 
• 1388167-49-4 (Z)-5-(4-chlorobenzylidene)-3-(2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl)imidazolidine-2,4-dione 
• 1388167-36-9 (Z)-5-(4-chlorobenzylidene)-3-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)imidazolidine-2,4-dione 
• 1388167-32-5 (Z)-5-(4-chlorobenzylidene)-3-(3-(4-(2-ethoxyphenyl)piperazin-1-yl)-2-hydroxypropyl)imidazolidine-2,4-dione 
• 1388167-21-2 C₁₃H₁₁ClN₂O₃ 

Relevant academic research and scientific papers

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

NOVEL N3-AMINOALKYL DERIVATIVES OF 5-ARYLIDENEHYDANTOIN, PHARMACEUTICAL COMPOSITION CONTAINING THE ABOVE AND APPLICATION THEREOF

The invention discloses novel 3-aminoalkyl derivatives of 5-arylidenehydantoin of formula I, pharmaceutical composition containing these derivatives and the use thereof in inhibition of efflux of drugs used to prevent and treat diseases of bacterial and/o

Search for new tools to combat Gram-negative resistant bacteria among amine derivatives of 5-arylidenehydantoin

A series of amine-alkyl derivatives of 5-arylidenehydantoin 3-21 was evaluated for their ability to improve antibiotic effectiveness in two strains of Gram-negative Enterobacter aerogenes: the reference strain (ATCC-13048) and the chloramphenicol-resistan

Synthesis and SAR-study for novel arylpiperazine derivatives of 5-arylidenehydantoin with α1-adrenoceptor antagonistic properties

The study is focused on a series of 5-arylidenehydantoin derivatives with a phenylpiperazine-hydroxypropyl fragment at N3 of the hydantoin ring. The compounds were assessed on their affinity for α1-adrenoceptors and evaluated in functional bioassays for their antagonistic properties. Crystal structures of (Z)-5-(4-chlorobenzylidene)-3-(3-(4-(2-ethoxyphenyl)piperazin-1- yl)-2-hydroxypropyl)imidazolidine-2,4-dione (7) and hydrochloride of (Z)-5-(4-chlorobenzylidene)-3-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl) propyl)imidazolidine-2,4-dione (10a) were solved using the X-ray diffraction method. Classical molecular mechanics (MMFFs force field, MCMM, MacroModel) were used to predict 3D structure of compounds 5a-18a using a crystal structure of 7. SAR analysis was performed on the basis of Barbaro's pharmacophore model and structural properties of previously investigated α1- adrenoceptor antagonists possessing a hydantoin fragment. Most of the compounds exhibited significant affinities for α1-ARs in nanomolar range (40-290 nM). The highest activities (Ki 1-affinities as follows: 3,4-di CH3O>2,4-di CH3O>4-Cl>2,3-di CH 3O>H>4-N(CH3)2.

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.

Synthesis and antitumor evaluation of novel cyclic arylsulfonylureas: ADME-T and pharmacophore prediction

Novel derivatives of 5-(substituted)benzylidene-3-(4-substituted)phenylsulfonylimidazolidine-2,4-diones (3a-r), 1-(4-substituted)phenylsulfonyl-3-(4-substituted)phenylpyrimidine-2,4,6-(1H,3H,5H)-triones (6a-l), and 3-(4-substituted)phenyl-1-(4-substituted)phenylsulfonylquinazoline-2,4(1H,3H)- diones (8a-l) have been synthesized and tested for their antitumor activity against 60 tumor cell lines taken from 9 different organs. The tested compounds have showed good inhibitory effect at the ovarian cancer (IGROV1) cell line. A significant inhibition for (RXF393) renal cancer cells was observed with series 3 compounds, while in the other two series 6 and 8, there was a significant inhibition of ovarian cancer cells (OVCAR-8) and melanoma cells (SK-MEL-2). Interestingly; beside the strong inhibition of compound 3q to IGROV1 and RXF393 cells, a great inhibition (199.62%) for (M14) Melanoma cells was observed at the tested concentration (10?μM). ADME-T and pharmacophore prediction methodology were used to study the antitumor activity of the most active compounds and to identify the structural features required for antitumor activity.

The marine natural-derived inhibitors of glycogen synthase kinase-3β phenylmethylene hydantoins: In vitro and in vivo activities and pharmacophore modeling

The Red Sea sponge Hemimycale arabica afforded the known (Z)-5-(4-hydroxybenzylidene)-hydantoin (1). This natural phenylmethylene hydantoin (PMH) 1 and the synthetic (Z)-5-(4-(ethylthio)benzylidene)-hydantoin (2) showed potent in vitro and in vivo anti-gr

Microwave-assisted solvent-free regiospecific synthesis of 5-alkylidene and 5-arylidenehydantoins

Hydantoins have become a well-known class of structures that have found significant applications as agrochemicals and therapeutics. This structural motif is of interest in the synthesis of small building blocks suitable for the preparation of potentially

Anticonvulsant Activity of Phenylmethylenehydantoins: A Structure-Activity Relationship Study

Phenylmethylenehydantoins (PMHs) and their des-phenyl analogues were synthesized and evaluated for anticonvulsant activity using the maximal electroshock seizure (MES) assay. The phenyl rings of PMHs were substituted with a wide spectrum of groups, and th

A new approach for the conversion of thiohydantoin to hydantoin derivatives

The reaction of thiohydantoins with 1-(bromoacetyl)benzenes afforded the corresponding hydantoin derivatives and 1-(mercaptoacetyl)benzenes instead of the expected oxoimidazothiazoles.