850859-09-5

Basic information

• Product Name: 2-([(4-BROMOPHENYL)METHYL]AMINO)ACETAMIDE
• Synonyms: 2-([(4-BROMOPHENYL)METHYL]AMINO)ACETAMIDE
• CAS NO: 850859-09-5
• Molecular Formula: C₉H₁₁BrN₂O
• Molecular Weight: 243.10044
• Mol File: 850859-09-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-([(4-BROMOPHENYL)METHYL]AMINO)ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-([(4-BROMOPHENYL)METHYL]AMINO)ACETAMIDE(850859-09-5)
• EPA Substance Registry System: 2-([(4-BROMOPHENYL)METHYL]AMINO)ACETAMIDE(850859-09-5)

Safety Data

• Hazardous Substances Data: 850859-09-5(Hazardous Substances Data)

Usage

Chemical Class

The compound belongs to the acetamide class of chemicals.

Molecular Weight

The molecular weight of the compound is 249.10 g/mol.

Physical Appearance

The compound is a white to off-white solid.

Solubility

The compound is soluble in organic solvents such as methanol, ethanol, and dimethyl sulfoxide.

Uses

The compound is commonly used as an intermediate in the synthesis of pharmaceuticals and organic compounds.

Pharmacological and Biological Activities

The presence of a bromophenyl group in its structure gives it potential pharmacological and biological activities, making it a valuable chemical for medicinal chemistry research.

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 1668-10-6 glycinamide hydrochloride 

Downstream Products

• 201987-81-7 1-(4-bromobenzyl)imidazolidine-2,4-dione 
• 1228594-48-6 1-(4-bromobenzyl)-3-cyclopropylimidazolidine-2,4-dione 
• 1228660-45-4 1-(4-Bromo-benzyl)-3-(2-methoxyethyl)imidazolidine-2,4-dione 
• 1338056-02-2 1-(4-(5-fluoro-6-(piperidin-1-ylmethyl)pyridin-2-yl)benzyl)-3-isobutylimidazolidine-2,4-dione 
• 1228659-57-1 1-(4-(5-fluoro-6-(piperidin-1-ylmethyl)pyridin-2-yl)benzyl)-3-propylimidazolidine-2,4-dione 
• 1228659-71-9 1-(4-(5-fluoro-6-(piperidin-1-ylmethyl)pyridin-2-yl)benzyl)-3-(2-methoxy-ethyl)imidazolidine-2,4-dione 
• 1228659-50-4 1-(4-(5-fluoro-6-(piperidin-1-ylmethyl)pyridin-2-yl)benzyl)-3-methylimidazolidine-2,4-dione 
• 1228659-61-7 1-(4-(6-((1,1-dioxo-1λ6-thiomorpholin-4-yl)methyl)-5-fluoropyridin-2-yl)benzyl)-3-propylimidazolidine-2,4-dione 

Relevant articles and documents

Structure-kinetic relationship studies of cannabinoid CB2 receptor agonists reveal substituent-specific lipophilic effects on residence time

A decade ago, the drug-target residence time model has been (re-)introduced, which describes the importance of binding kinetics of ligands on their protein targets. Since then, it has been applied successfully for multiple protein targets, including GPCRs, for the development of lead compounds with slow dissociation kinetics (i.e. long target residence time) to increase in vivo efficacy or with short residence time to prevent on-target associated side effects. To date, this model has not been applied in the design and pharmacological evaluation of novel selective ligands for the cannabinoid CB2 receptor (CB2R), a GPCR with therapeutic potential in the treatment of tissue injury and inflammatory diseases. Here, we have investigated the relationships between physicochemical properties, binding kinetics and functional activity in two different signal transduction pathways, G protein activation and β-arrestin recruitment. We synthesized 24 analogues of 3-cyclopropyl-1-(4-(6-((1,1-dioxidothiomorpholino)methyl)-5-fluoropyridin-2-yl)benzyl)imidazoleidine-2,4-dione (LEI101), our previously reported in vivo active and CB2R-selective agonist, with varying basicity and lipophilicity. We identified a positive correlation between target residence time and functional potency due to an increase in lipophilicity on the alkyl substituents, which was not the case for the amine substituents. Basicity of the agonists did not show a relationship with affinity, residence time or functional activity. Our findings provide important insights about the effects of physicochemical properties of the specific substituents of this scaffold on the binding kinetics of agonists and their CB2R pharmacology. This work therefore shows how CB2R agonists can be designed to have optimal kinetic profiles, which could aid the lead optimization process in drug discovery for the study or treatment of inflammatory diseases.

HETEROCYCLIC DERIVATIVES

The present invention relates to a heterocyclic derivative of formula (I) wherein the variables are as defined in the specification, or to a pharmaceutically acceptable salt or solvate thereof. The present invention further relates to pharmaceutical compositions comprising said heterocyclic derivatives and to their use in therapy, for instance in the treatment or prevention of disorders mediated by glutamate dysfunction, such as schizophrenia and generalised anxiety disorder.

Discovery and optimization of 1-(4-(Pyridin-2-yl)benzyl)imidazolidine-2,4- dione derivatives as a novel class of selective cannabinoid CB2 receptor agonists

Here, we report the identification and optimization of 1-(4-(pyridin-2-yl) benzyl)imidazolidine-2,4-dione derivatives as a novel chemotype with selective cannabinoid CB2 receptor agonist activity. 1 is a potent and selective cannabinoid CB2 receptor agonist (hCB2 pEC50 = 8.6). The compound was found to be metabolically unstable, which resulted in low oral bioavailability in rat (Fpo = 4%) and possessed off-target activity at the hERG ion channel (pKi = 5.5). Systematic modification of physicochemical properties, such as lipophilicity and basicity, was used to optimize the pharmacokinetic profile and hERG affinity of this novel class of cannabinoid CB2 receptor agonists. This led to the identification of 44 as a potent, selective, and orally bioavailable cannabinoid CB2 receptor agonist (hCB2 pEC50 = 8.0; hERG pKi po = 100%), which was active in a rat spinal nerve ligation model of neuropathic pain.

1-(4-(PYRIDIN-2-YL)BENZYL)IMIDAZOLIDINE-2,4-DIONE DERIVATIVES

The invention relates to 1-(4-(pyridin-2-yl)benzyl)imidazolidine-2,4-dione derivative having the general Formula I wherein R1 is H, (C1-6)alkyl (optionally substituted with oxo, (C1-3)alkyloxy, (C1-3)alkyloxycar