Hydantoin

Base Information

• Chemical Name: Hydantoin
• CAS No.: 461-72-3
• Deprecated CAS: 345341-10-8,1394977-74-2
• Molecular Formula: C3H4N2O2
• Molecular Weight: 100.077
• Hs Code.: 2933.21
• European Community (EC) Number: 207-313-3
• NSC Number: 9226
• UNII: I6208298TA
• DSSTox Substance ID: DTXSID1052111
• Nikkaji Number: J2.588G
• Wikipedia: Hydantoin
• Wikidata: Q418082
• RXCUI: 1721294
• Pharos Ligand ID: VRC4FF9N4ZH5
• Metabolomics Workbench ID: 51389
• ChEMBL ID: CHEMBL122334
• Mol file: 461-72-3.mol

Synonyms:Hydantoin;Hydantoins;Imidazolidine 2,4 Diones;Imidazolidine-2,4-Diones

Chemical Property of Hydantoin

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0.00448mmHg at 25°C
• Melting Point: 218-220 °C(lit.)
• Refractive Index: 1.702
• Boiling Point: 246.4°C at 760 mmHg
• PKA: pKa 9.1 (Uncertain)
• Flash Point: 102.8°C
• PSA: 58.20000
• Density: 1.357 g/cm³
• LogP: -0.51660
• Storage Temp.: Store below +30°C.
• Solubility.: SLIGHTLY SOLUBLE
• Water Solubility.: SLIGHTLY SOLUBLE
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 100.027277375
• Heavy Atom Count: 7
• Complexity: 120

Purity/Quality:

99%min ^*data from raw suppliers

Hydantoin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Imidazoles
• Canonical SMILES: C1C(=O)NC(=O)N1
• General Description: Hydantoin derivatives, particularly phenylmethylene hydantoin (PMH), exhibit promising anti-metastatic properties by inhibiting prostate cancer cell invasion and migration. The inhibitory activity of these compounds is influenced by key physicochemical parameters such as molecular volume and log P, as identified through QSAR analysis. PMH represents a novel therapeutic lead class with potential applications in prostate cancer treatment.

Technology Process of Hydantoin

There total 133 articles about Hydantoin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

chloroacetyl chloride (79-04-9) + urea (57-13-6) → 2,4-imidazolidinedione (461-72-3)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; Solvent; Cooling with ice;

Reference yield: 86.0%

1-acetyl-2-thiohydantoin (584-26-9) → 2,4-imidazolidinedione (461-72-3)

Guidance literature:

With water; chloroacetic acid; for 2h; Reflux;

Reference yield: 84.0%

2-thiohydantoin (503-87-7) → 2,4-imidazolidinedione (461-72-3)

Guidance literature:

With tetrabutylammonium periodite; In dichloromethane; acetonitrile; at 20 ℃; for 2h;

DOI:10.1007/s00706-005-0289-8

upstream raw materials:

Allantoin

4,5-dihydroxy-2-imidazolidinone

parabanic acid

cyanomethylurea

Downstream raw materials:

(Z)-5-(1H-pyrrol-2-ylmethylene)-imidazolidine-2,4-dione

5-furfurylidene-imidazolidine-2,4-dione

5-thiophen-2-ylmethylene-imidazolidine-2,4-dione

5-(3-indolylmethylene)hydantoin

Refernces

Phenylmethylene hydantoins as prostate cancer invasion and migration inhibitors. CoMFA approach and QSAR analysis

10.1016/j.ejmech.2010.08.066

The research focuses on the discovery and optimization of phenylmethylene hydantoin (PMH) derivatives as potential inhibitors of prostate cancer invasion and migration. The study utilized a 3D-QSAR CoMFA model for virtual screening of commercially available PMH derivatives to identify those with enhanced anti-migratory and anti-invasive activities. Experiments involved the synthesis of PMH derivatives using base-catalyzed condensation of hydantoin with substituted benzaldehydes, followed by biological evaluation using wound-healing assays and Cultrex invasion assays. The analysis included NMR spectroscopy for structural confirmation, MTT assays for cytotoxicity evaluation, and QSAR analysis to establish a predictive model with physicochemical descriptors such as molecular volume and log P, which were identified as critical parameters for the inhibitory activity of methylene hydantoins. The research demonstrated that PMH is a novel anti-metastatic lead class with potential therapeutic activity against prostate cancer.