10040-87-6

Usage

Uses

Used in Pharmaceutical Synthesis:
5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione is utilized as a key intermediate in the synthesis of pharmaceuticals for its ability to form complex molecular structures that can exhibit therapeutic properties.
Used in Agrochemical Production:
In the agrochemical industry, 5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione serves as a crucial component in the development of new compounds designed to protect crops and enhance agricultural productivity.
Used in Organic Chemistry Research:
As a versatile building block, 5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione is used in organic chemistry research to explore novel reactions and mechanisms, contributing to the advancement of chemical knowledge and the discovery of new synthetic pathways.
Used as a Ligand in Organometallic Chemistry:
The dimethylamino group in 5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione makes it an effective ligand for use in organometallic chemistry, where it can influence the properties and reactivity of metal complexes.
Used in Catalysis:
5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione's structural features make it suitable for use in catalytic processes, where it can facilitate or enhance the rate of chemical reactions, improving the efficiency of industrial and laboratory processes.

Upstream product

• 461-72-3 2,4-imidazolidinedione 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 120-21-8 4-Diethylaminobenzaldehyde 
• 41250-31-1 5-(4-dimethylamino-benz-(Z)-ylidene)-2-thioxo-imidazolidin-4-one 
• 95378-36-2 diethyl 2,4-dioxoimidazolidin-5-yl-phosphonate 

Downstream Products

• 58841-92-2 5-(4-dimethylaminobenzyl)imidazolidine-2,4-dione 
• 924863-99-0 2-[5-(4-dimethylamino-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide 
• 1388167-46-1 (Z)-5-(4-(dimethylamino)benzylidene)-3-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)imidazolidine-2,4-dione 
• 1388167-51-8 (Z)-5-(4-(dimethylamino)benzylidene)-3-(3-(4-(2-ethoxyphenyl)piperazin-1-yl)-2-hydroxypropyl)imidazolidine-2,4-dione 
• 1416719-85-1 C₁₇H₂₁N₃O₃ 
• 1388167-22-3 C₁₅H₁₇N₃O₃ 

Relevant academic research and scientific papers

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

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

Privileged scaffolds or promiscuous binders: A comparative study on rhodanines and related heterocycles in medicinal chemistry

Rhodanines and related five-membered heterocycles with multiple heteroatoms have recently gained a reputation of being unselective compounds that appear as "frequent hitters" in screening campaigns and therefore have little value in drug discovery. However, this judgment appears to be based mostly on anecdotal evidence. Having identified various rhodanines and related compounds in screening campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed. The results indicate that the exocyclic, double bonded sulfur atom in rhodanines and thiohydantoins, in addition to other structural features, offers a particularly high density of interaction sites for polar interactions and hydrogen bonds. This causes a promiscuous behavior at concentrations in the "screening range" but should not be regarded as a general knockout criterion that excludes such screening hits from further development. It is suggested that special criteria for target affinity and selectivity are applied to these classes of compounds and that their exceptional and potentially valuable biomolecular binding properties are consequently exploited in a useful way.

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.

Optimization of (phenylmethylidene)-hydantoins as prostate cancer migration inhibitors: SAR-directed design, synthesis, and pharmacophore modeling

Prostate cancer is one of the most common cancer forms among males of Western countries. Natural products proved to be an unparalleled source of molecular diversity. The 4-(hydroxyphenylmethylidene)hydantoin (PMH; 1), (5Z)-5-(4-hydroxybenzylidene)imidazolidine-2,4-dione, was isolated from the Red Sea sponge Hemimycale arabica, and recently showed junctional complexes stabilization, anti-invasive, and antimetastatic activities in vitro and in vivo. The related synthetic analogue, (5Z)-5-[4-(ethylsulfanyl)benzylidene] imidazolidine-2,4-dione (2), showed several-fold-improved in vivo antimetastatic properties against the highly invasive prostate cancer. To further optimize the activity of PMHs, various ligand-based strategies were used including the extension of the structure, structural simplification, linker extension, and computer-assisted CoMFA (Comparative Molecular Field Analysis) results. These strategies yielded thirty 2nd-generation PMHs, designed based on the 1st-generation PMHs, such as 1 and 2. Wound-healing assay was selected to evaluate the in vitro anti-migratory potential of these new PMHs against the PC-3 cell line. Several active PMHs, including 10, 13, 24, 29, with nearly twelvefold enhancement of activity vs. 2, were identified. Active compounds were then used to build a pharmacophore model using the SYBYL's DIStance COmparison technique (DISCOtech). Active PMHs were also screened for fragment-based drug likeness using the OSIRIS program, and an overall drug score was also calculated. Interestingly, the overall drug scores of 24 and 29 along with their anti-migratory activity were significantly greater than those of 1 and 2. In conclusion, PMHs can be the appropriate scaffolds for the urgently needed drug candidates for the control of androgen independent prostate cancer. Copyright

Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice

A large amount of evidence suggests that monocytes/macrophages infiltration is implicated in a variety of inflammatory diseases including acute liver injury. Monocyte chemoattractant protein 1 (MCP-1) plays a crucial role in the process of macrophages recruitment. We herein presented a small-molecule library and a feasible quick screening method of evaluating potency of inhibition of chemotaxis of RAW264.7 cells stimulated by MCP-1. Fifty-three small molecules were synthesized and screened, and four compounds (2g, 2h, 4f, and 6h) showed inhibitory effects with IC50 values range from 0.72 to 20.47 μM, with compound 4f being the most efficient. Further in vivo studies demonstrated that oral administration of 2g, 2h, 4f, or 6h decreases, most significantly for 4f, the serum levels of alanine aminotransaminase (ALT) and asparate aminotransaminase (AST) in ConA-induced acute livery injury BALB/c mice. Histopathological evaluation liver sections confirmed 4f as a potent, orally active compound for hepatoprotective effects against ConA-induced acute liver injury in BALB/c mice.

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.

Synthesis and in vitro anticancer activity of 2,4-azolidinedione-acetic acids derivatives

The synthesis and evaluation of anticancer activity of 2,4-thia(imida)zolidinedione-3- and 5-acetic acids amides were described. The structures of compounds were determined by IR, 1H NMR, and MS analysis. In vitro anticancer activity of these compounds has been tested in National Cancer Institute (NCI) and the relationships between structure and anticancer activity are discussed. Among 2,4-azolidinedione-acetic acids derivatives 2-[5-(4-chlorobenzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide (Ic) was superior to other related compounds in terms of high selectivity for the leukemia CCRF-CEM (log GI50 = -6.06), HL-60(TB) (log GI50 = -6.53), MOLT-4 (log GI50 = -6.52) and SR (log GI50 = -6.51) cell lines.

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

Synthesis, reactions and conformational analysis of 5-arylidene-2-thiohydantoins as potential antiviral agents

(Z)-5-Arylidene-1-(4-methylphenylsulfonyl)-2-thiohydantoins 5a,b were synthesized from the direct condensation of the aromatic aldehydes 4a,b with 1-(4-methylphenylsulfonyl)-2-thiohydantoins 3a,b. Compounds 5a,b were coupled with 2′-deoxy-3′,5′-di(4-methylbenzoyl)-α-D-erythro-pentofura nosyl chloride 6 under alkaline conditions to afford N3-protected nucleosides 7a,b. Reaction of 5a,b with chloromethyl methyl sulfide and/or 2-bromoacetaldehyde diethyl acetal in alkaline medium afforded N3-alkyl derivatives 8a-c. Reaction of 5a with 1,2-dichloroethane in alkaline conditions afforded bis-thiohydantoinylethane 9a,b. Compounds 5a,b were condensed with formaldehyde and secondary amines to afford 3-aminomethyl-2-thiohydantoins derivatives 10a-d. On the other hand, reaction of unsubstituted 2-thiohydantoins derivatives 11b,c with chloromethyl methyl sulfide afforded the mono- and bis-methylthio derivatives 12a,b and 13a,b, respectively. Reaction of 11b,c with secondary amines and formaldehyde gave 3-aminomethyl-2-thiohydantoins 14a-e. Reaction of 11a-C with bromoacetaldehyde diethyl acetal yielded the S-alkyl derivatives 15a-c which can be hydrolysed with ethanolic hydrochloric acid to afford 5-arylidenehydantoins 16a-c. The compounds do not display any antiviral activity.