67337-72-8

Basic information

• Product Name: 5-(4-hydroxybenzyl)imidazolidine-2,4-dione
• Synonyms: 2,4-imidazolidinedione, 5-[(4-hydroxyphenyl)methyl]-
• CAS NO: 67337-72-8
• Molecular Formula: C₁₀H₁₀N₂O₃
• Molecular Weight: 206.198
• Mol File: 67337-72-8.mol
• Article Data: 3

Chemical Properties

• Density: 1.37g/cm³
• Refractive Index: 1.605
• CAS DataBase Reference: 5-(4-hydroxybenzyl)imidazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-hydroxybenzyl)imidazolidine-2,4-dione(67337-72-8)
• EPA Substance Registry System: 5-(4-hydroxybenzyl)imidazolidine-2,4-dione(67337-72-8)

Safety Data

• Hazardous Substances Data: 67337-72-8(Hazardous Substances Data)

Upstream product

• 80171-33-1 5-(p-hydroxybenzylidene)hydantoin 
• 57-13-6 urea 
• 590-28-3 potassium cyanate 
• 60-18-4 L-tyrosine 
• 16652-64-5 O-benzyl-S-tyrosine 
• 80171-33-1 5-(4-hydroxybenzylidene)imidazolidine-2,4-dione 
• 6318-40-7 (5Z)-5-(4-hydroxybenzylidene)-2-thioxoimidazolidin-4-one 
• 123-08-0 4-hydroxy-benzaldehyde 
• 54896-65-0 N-carbamoyltyrosine 
• 556-02-5 ?Tyr 

Downstream Products

• 54896-58-1 N-carbamyl-D-tyrosine 
• 90899-85-7 N-carbamoyl-L-tyrosine 
• 54896-65-0 N-carbamoyltyrosine 

Relevant articles and documents

Synthesis, crystal structure, hydrogen bond patterns and Hirshfeld surface analysis of (S)-5-(4-hydroxybenzyl)-imidazolidine-2,4?dione

The title compound, (S)-5-(4-hydroxybenzyl)-imidazolidine-2,4?dione, a new α-amino acid hydantoin derivative with formula C10H10N2O3 has been synthesized and structurally characterized by MS, FT-IR, NMR, and X-ray diffraction techniques. Spectroscopy results are consistent with the skeleton structure. The powder X-ray diffraction data confirms the phase purity of the crystalline sample. Single-crystal X-ray diffraction analysis indicated that crystallizes in the orthorhombic space group P212121 (N°19), Z = 4, and unit cell parameters a = 6.217(3) ?, b = 7.653(3) ?, c = 19.824(8) ?. The molecular structure and crystal packing are stabilized by intermolecular N–H···O and O–H···O hydrogen formed infinite two-dimensional chains, with graph-set C(6), C(5) and C(11) that run along the a, b and c directions forming a two-dimensional network. Hirshfeld surface analysis confirm that the most important contributions for the crystal packing are from N–H··O and O–H··O interactions. Energy framework calculations suggest that the contacts formed between molecules are slightly electrostatic and revealed that interactions exhibit approximately complex zig-zag shape topology in the crystal structure.

Discovery of novel 2,5-dioxoimidazolidine-based P2X7 receptor antagonists as constrained analogues of KN62

Novel 2,5-dioxoimidazolidine-based conformationally constrained analogues of KN62 (1) were developed as P2X7 receptor (P2X7R) antagonists using a rigidification strategy of the tyrosine backbone of 1. SAR analysis of the 2,5-dioxoimidazolidine scaffold indicated that piperidine substitution at the N3 position and no substitution at N1 position were preferable. Further optimization of the substituents at the piperidine nitrogen and the spacer around the skeleton resulted in several superior antagonists to 1, including 1-adamantanecarbonyl analogue 21i (IC50 = 23 nM in ethidium uptake assay; IC50 = 14 nM in IL-1β ELISA assay) and (3-CF3-4-Cl)benzoyl analogue (-)-21w (54 nM in ethidium uptake assay; 9 nM in IL-1β ELISA assay), which was more potent than the corresponding (+) isomer. Compound 21w displayed potent inhibitory activity in an ex vivo model of LTP-induced pain signaling in the spinal cord and significant anti-inflammatory activity in in vivo models of carrageenan-induced paw edema and type II collagen-induced joint arthritis.