22927-78-2

Basic information

• Product Name: 5-(p-methoxyphenyl)-5-methyl-hydantoi
• Synonyms: 5-(p-methoxyphenyl)-5-methyl-hydantoi
• CAS NO: 22927-78-2
• Molecular Formula: C₁₁H₁₂N₂O₃
• Molecular Weight: 220.22458
• Mol File: 22927-78-2.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.22g/cm³
• Refractive Index: 1.539
• CAS DataBase Reference: 5-(p-methoxyphenyl)-5-methyl-hydantoi(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(p-methoxyphenyl)-5-methyl-hydantoi(22927-78-2)
• EPA Substance Registry System: 5-(p-methoxyphenyl)-5-methyl-hydantoi(22927-78-2)

Safety Data

• Hazardous Substances Data: 22927-78-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H12N2O3/c1-11(9(14)12-10(15)13-11)7-3-5-8(16-2)6-4-7/h3-6H,1-2H3,(H2,12,13,14,15)/t11-/m1/s1

Upstream product

• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 7732-18-5 water 
• 506-87-6 ammonium carbonate 
• 773837-37-9 sodium cyanide 
• 100-66-3 methoxybenzene 
• 143-33-9 sodium cyanide 

Downstream Products

• 98402-10-9 5-(4-Methoxy-phenyl)-5-methyl-1,3-bis-morpholin-4-ylmethyl-imidazolidine-2,4-dione 
• 134721-55-4 5-(4-Methoxy-phenyl)-3,5-dimethyl-imidazolidine-2,4-dione 
• 74279-63-3 2-(4-methoxyphenyl)-2-methylglycine 
• 1186115-79-6 5-(4-methoxyphenyl)-5-methyl-3-(4-(2-oxo-8-n-propyl-4-(trifluoromethyl)-2H-chromen-7-yloxy)butyl)imidazolidine-2,4-dione 
• 1186118-06-8 5-(4-methoxyphenyl)-5-methyl-3-(4-(2-oxo-6,8-di-n-propyl-4-(trifluoromethyl)-2H-chromen-7-yloxy)butyl)imidazolidine-2,4-dione 
• 1031395-70-6 3-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2,6-di-n-propylphenoxy)-butyl)-5-(4-methoxyphenyl)-5-methylimidazolidine-2,4-dione 
• 1031393-87-9 3-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-n-propylphenoxy)butyl)-5-(4-methoxyphenyl)-5-methylimidazolidine-2,4-dione 
• 197643-97-3 C₁₂H₁₅NO₄ 
• 959694-01-0 (S)-4-[3,4-dimethyl-2,5-dioxo-4-(4-methoxyphenyl)imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile 
• 959691-71-5 (R)-4-[3,4-dimethyl-2,5-dioxo-4-(4-methoxyphenyl)imidazolidin-1-yl]-2-methoxybenzonitrile 

Relevant articles and documents

Computer-aided insights into receptor-ligand interaction for novel 5-arylhydantoin derivatives as serotonin 5-HT7 receptor agents with antidepressant activity

This paper presents a computer-aided insight into the receptor-ligand interaction for novel analogs of the lead structure 5-(4-fluorophenyl)-3-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-5-methylimidazolidine-2,4-dione (1, MF-8), as part of the search for potent and selective serotonin 5-HT7 receptor (5-HT7R) agents. New hydantoin derivatives (4-19) were designed and synthesized. For 5-phenyl-3-(2-hydroxy-3-(4-(2-ethoxyphenyl)piperazin-1-yl)propyl)-5-methylimidazolidine-2,4-dione (4), its crystal structure was determined experimentally. Molecular modeling studies were performed, including both pharmacophore and structure-based approaches. New compounds were investigated in radioligand binding assays (RBA) for their affinity toward 5-HT7R and selectivity over 5-HT1AR, dopamine D2R and α1-, α2-and β-adrenoceptors. Selected compounds (5-8) were assessed for their antidepressant and anxiolytic effects in vivo in mice. Most of the tested compounds displayed potent affinity and selectivity for 5-HT7R in RBA, in particular seven compounds (4, 5, 7, 8 and 10-12, Ki ≤ 10 nM). Antidepressant-like activity in vivo for all tested compounds (5-8) was confirmed. SAR analysis based on both crystallography-supported molecular modeling and RBA results indicated that mono-phenyl substituents at both hydantoin and piperazine are more favorable for 5-HT7R affinity than the di-phenyl ones.

Design, synthesis and pharmacology of 1,1-bistrifluoromethylcarbinol derivatives as liver X receptor β-selective agonists

A novel series of 1,3-bistrifluoromethylcarbinol derivatives that act as liver X receptor (LXR) β-selective agonists was discovered. Structure-activity relationship studies led to the identification of molecule 62, which was more effective (Emax) and selective toward LXRβ than T0901317 and GW3965. Furthermore, 62 decreased LDL-C without elevating the plasma TG level and significantly suppressed the lipid-accumulation area in the aortic arch in a Bio F1B hamster fed a diet high in fat and cholesterol. We demonstrated that our LXRβ agonist would be potentially useful as a hypolipidemic and anti-atherosclerotic agent. In this manuscript, we report the design, synthesis and pharmacology of 1,3-bistrifluoromethylcarbinol derivatives.

Design and discovery of 2-oxochromene derivatives as liver X receptor β-selective agonists

In an attempt to molecularly design liver X receptor (LXR) β-selective agonists, we discovered that the combination of the 2-oxochromene moiety (head) and the imidazoline-2,4-dione moiety (tail) plays an important role in the expression potency and select

Solvent effects on the absorption spectra of potentially pharmacologically active 5-alkyl-5-arylhydantoins: A structure-property relationship study

To obtain insight into the interactions of potential anticonvulsant drugs with their surrounding, two series of 5-methyl-5-aryl- and 5-ethyl-5- -arylhydantoins were synthesized and their absorption spectra were recorded in the region from 200 to 400 nm in a set of selected solvents. The effects of solvent dipolarity/polarizability and solvent-solute hydrogen bonding interactions on the absorption maxima shifts were analyzed by means of the linear solvation energy relationship (LSER) concept of Kamlet and Taft. The ratio of the contributions of specific and non-specific solvent-solute interactions were correlated with the corresponding absorption, distribution, metabolism, and excretion (ADME) properties of the studied compounds. The correlation equations were combined with different physicochemical parameters to generate new equations, which demonstrate the reasonable relationships between the solvent- solute interactions and the structure-activity parameters. Copyright (C)2013 SCS.

CARBINOL DERIVATIVES HAVING CYCLIC LINKER

[Object] To provide a novel LXRβ agonist that is useful as a preventative and/or therapeutic agent for atherosclerosis; arteriosclerosis such as those resulting from diabetes; dyslipidemia; hypercholesterolemia; lipid-related diseases; inflammatory diseases that are caused by inflammatory cytokines; skin diseases such as allergic skin diseases; diabetes; or Alzheimer's disease. [Solving Means] A carbinol compound represented by the following general formula (I) or salt thereof, or their solvate.

Hydrophobic and electronic factors in the design of dialkylglycine decarboxylase mimics

The first functional catalytic mimic of the enzyme dialkylglycine decarboxylase is described. This system utilizes a hydrophobically modified polyethylenimine polymer, a pyridoxamine cofactor, and a 2-aryl-2-alkylglycine sacrificial amine source to convert α-keto acids to α-amino acids at biologically relevant temperatures with multiple turnovers of the pyridoxamine catalyst. The effects of hydrophobic and electronic factors in the 2,2-disubstituted sacrificial amine source and the pyridoxamine catalyst on turnover frequency and turnover number are explored.

BMS-201620: A selective beta 3 agonist

A series of N-(4-hydroxy-3-methylsulfonanilidoethanol)arylglycinamides were prepared and evaluated for their human β3 adrenergic receptor agonist activity. SAR studies led to the identification of BMS-201620 (39), a potent β3 full agonist (Ki=93nM, 93% activation). Based on its favorable safety profile, BMS-201620 was chosen for clinical evaluation.

CATECHOLAMINE SURROGATES USEFUL AS BETA 3 AGONISTS

Compounds of the formula STR1 and pharmaceutically acceptable salts thereof. These compounds are beta three adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity and gastrointestinal diseases.

Ultrasound-promoted synthesis of 5-substituted and 5,5-disubsntuted hydantoins

Sonication of a mixture of industrial grade sodium cyanide (aqueous solution) and ammonium carbonate in aqueous alcohol with aldehydes or ketones affords the 5-substituted or 5,5-disubstituted hydantoins in 30-92percent yield.