6330-09-2

Basic information

• Product Name: 5-Benzyl-2-thioxo-4-imidazolidone
• Synonyms: 5-Benzyl-2-thiohydantoin;5-Benzyl-2-thioxo-4-imidazolidone
• CAS NO: 6330-09-2
• Molecular Formula: C₁₀H₁₀N₂OS
• Molecular Weight: 206.2642
• Mol File: 6330-09-2.mol

Chemical Properties

• Appearance: /
• Density: 1.32 g/cm³
• Refractive Index: 1.664
• CAS DataBase Reference: 5-Benzyl-2-thioxo-4-imidazolidone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Benzyl-2-thioxo-4-imidazolidone(6330-09-2)
• EPA Substance Registry System: 5-Benzyl-2-thioxo-4-imidazolidone(6330-09-2)

Safety Data

• Hazardous Substances Data: 6330-09-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Benzyl-2-thioxo-4-imidazolidone is utilized as a pharmaceutical agent for its anti-inflammatory and analgesic properties, offering potential relief for conditions characterized by inflammation and pain.
Used in Organic Synthesis:
In the field of organic synthesis, 5-Benzyl-2-thioxo-4-imidazolidone serves as a valuable building block, contributing to the creation of a variety of complex organic molecules and compounds.
Used in Cancer Research and Treatment:
5-Benzyl-2-thioxo-4-imidazolidone is employed as a subject of interest in cancer research due to its reported anti-cancer activity. It is being investigated for its potential to contribute to the development of novel cancer treatments, particularly given its demonstrated effectiveness against cancer cells.

InChI:InChI=1/C10H10N2OS/c13-9-8(11-10(14)12-9)6-7-4-2-1-3-5-7/h1-5,8H,6H2,(H2,11,12,13,14)

Upstream product

• 583-46-0 5-benzylidene-2-thiohydantoin 
• 150-30-1 Phenylalanine 
• 17356-08-0 thiourea 
• 104509-53-7 1-acetyl-5-benzyl-2-thioxoimidazolidin-4-one 
• 1147550-11-5 ammonium thiocyanate 
• 583-47-1 4-benzyl-oxazolidine-2,5-dione 
• 108-24-7 acetic anhydride 
• 95474-44-5 (5Z)-5-benzylidene-2-thioxo-imidazolidin-4-one 
• 100-52-7 benzaldehyde 

Downstream Products

• 1065502-39-7 C₁₄H₁₆N₂O₂S 

Relevant articles and documents

Diastereoselective synthesis of pyrrolo[1, 2-c]imidazoles using chiral thiohydantoins, malononitrile, and aldehydes and evaluation of their antioxidant and antibacterial activities

Diastereoselective synthesis of pyrrolo[1,2-c]imidazoles is reported from three-component reaction of chiral thiohydantoins, aldehydes, and malononitrile in the presence of NEt3. The antioxidant properties of the obtained products were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. Among the products, compound 4l possessing NH2 and NH groups and bromine atom at 4-position of the aromatic ring displayed the highest antioxidant activity (90%). Also, their antibacterial activities were explored against gram-positive and gram-negative bacteria using disc diffusion method. Among the synthesized compounds, 4a with chlorine atom at para position of the aromatic ring, and methyl group (the smallest alkyl group) at 7-position, displayed the best antibacterial activity against the tested gram-positive bacteria.

Enantioselective Synthesis of 5,5-Disubstituted Hydantoins by Br?nsted Base/H-Bond Catalyst Assisted Michael Reactions of a Design Template

A new method for the enantioselective synthesis of 5,5-disubstituted (quaternary) hydantoins was developed on the basis of an organocatalytic Michael reaction approach involving the use of 2-benzylthio-3,5-dihydroimidazol-4-ones as key hydantoin surrogates. The method is general with respect to the substitution pattern at the hydantoin N1 (alkyl, aryl, acyl), N3 (aryl), and C5 (linear/branched alkyl, aryl) positions and affords essentially single diastereomeric products with enantioselectivities higher than 95 % ee in most cases. Among the bifunctional Br?nsted base/H-bond catalysts examined, a known squaramide–tertiary amine catalyst and a newly prepared squaramide–tertiary amine catalyst provide the highest selectivity so far with either nitroolefins or vinyl ketones as the acceptor components. Kinetic measurements support a first-order rate dependence on both reaction partners, the donor template and the Michael acceptor, whereas competitive 1H NMR spectroscopy experiments reveal the high ability of the template for catalyst binding.

Systematic Evaluation of the Metabolism and Toxicity of Thiazolidinone and Imidazolidinone Heterocycles

The thiazolidine and imidazolidine heterocyclic scaffolds, i.e., the rhodanines, 2,4-thiazolidinediones, 2-thiohydantoins, and hydantoins have been the subject of debate on their suitability as starting points in drug discovery. This attention arose from the wide variety of biological activities exhibited by these scaffolds and their frequent occurrence as hits in screening campaigns. Studies have been conducted to evaluate their value in drug discovery in terms of their biological activity, chemical reactivity, aggregation-based promiscuity, and electronic properties. However, the metabolic profiles and toxicities have not been systematically assessed. In this study, a series of five-membered multiheterocyclic (FMMH) compounds were selected for a systematic evaluation of their metabolic profiles and toxicities on TAMH cells, a metabolically competent rodent liver cell line and HepG2 cells, a model of human hepatocytes. Our studies showed that generally the rhodanines are the most toxic, followed by the thiazolidinediones, thiohydantoins, and hydantoins. However, not all compounds within the family of heterocycles were toxic. In terms of metabolic stability, 5-substituted rhodanines and 5-benzylidene thiohydantoins were found to have short half-lives in the presence of human liver microsomes (t1/2 30 min) suggesting that the presence of the endocyclic sulfur and thiocarbonyl group or a combination of C5 benzylidene substituent and thiocarbonyl group in these heterocycles could be recognition motifs for P450 metabolism. However, the stability of these compounds could be improved by installing hydrophilic functional groups. Therefore, the toxicities and metabolic profiles of FMMH derivatives will ultimately depend on the overall chemical entity, and a blanket statement on the effect of the FMMH scaffold on toxicity or metabolic stability cannot and should not be made.

SYNTHESIS OF IMIDAZOLE-2-THIONES VIA THIOHYDANTOINS

The present invention provides a method of making an imidazole 2-thione which comprises the step(s) of reducing a thiohydantoin to said imidazole- 2-thione.

Structure and activity studies of glycine receptor ligands. Part 8. Arylidene-imidazoline-4-one aminoacids

Based on chemical and preliminary biological experiments (inhibition to glycine receptor), structure and activity relationship of arylidene-imidazoline-4-one amino acids has been studied. In the course of our work, the simulation of the hydrogen bonds formation between ligand molecule and hypothetical receptor has been designed. Computed interactions are going to simulate possible ligand-receptor interaction with selected amino acids (in this investigation - with basic lysine and acidic aspartic acid). Obtained model estimates roughly the binding energy of the amino acids with ligand molecules. The proposed amino acids binding energies approximately agree with activity of the isomeric benzylidene-imidazoline-4-one glycines and α-alanines which decreases in the order of m-Cl > p-Cl > o-Cl substituents in benzylidene moiety. Additionally, the lowering of activity is caused by lipophilic pocket volume.