5426-70-0

Usage

Molecular Weight

302.30 g/mol

Structure

A purine derivative with a dimethyl group and a phenoxymethyl group attached to the purine ring

Parent Compound

Xanthine (a naturally occurring compound)

Applications

a. Research tool in biochemistry and pharmacology
b. Potential use in the pharmaceutical industry for drug development

Biological Activity

Potential biological activity, but further research is needed to understand its properties and potential uses

Solubility

Not explicitly mentioned, but likely soluble in organic solvents due to its structure

Stability

Not explicitly mentioned, but generally stable under normal laboratory conditions

Appearance

Not explicitly mentioned, but likely a solid or crystalline substance based on its molecular weight and structure

Purity

Not explicitly mentioned, but typically synthesized with high purity for research purposes

Safety

Not explicitly mentioned, but should be handled with care due to its potential biological activity and unknown side effects

Storage

Not explicitly mentioned, but should be stored in a cool, dry place, away from light and moisture to maintain stability

Synthesis

Not explicitly mentioned, but likely synthesized through chemical reactions involving the parent compound xanthine and the appropriate reagents to introduce the dimethyl and phenoxymethyl groups

Analysis

Not explicitly mentioned, but its structure and properties can be analyzed using techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and elemental analysis.

Upstream product

• 701-99-5 Phenoxyacetyl chloride 
• 122-59-8 2-phenoxyacetic acid 
• 5440-00-6 4,5-Diamino-1,3-dimethyluracil 
• 166115-79-3 N-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-2-phenoxy-acetamide 

Downstream Products

• 1388725-76-5 8-(phenoxymethyl)-1,3,7-trimethylxanthine 

Relevant academic research and scientific papers

1,3,7-Triethyl-substituted xanthines - Possess nanomolar affinity for the adenosine A1 receptor

Adenosine A1 receptors are attracting great interest as drug targets for their role in cognitive deficits. Antagonism of the adenosine A1 receptor may offer therapeutic benefits in complex neurological diseases, such as Alzheimer's and Parkinson's disease. The aim of this study was to discover potential selective adenosine A1 receptor antagonists. Several analogs of 8-(3-phenylpropyl)xanthines (3), 8-(2-phenylethyl)xanthines (4) and 8-(phenoxymethyl)xanthines (5) were synthesized and assessed as antagonists of the adenosine A1 and A2A receptors via radioligand binding assays. The results indicated that the 1,3,7-triethyl-substituted analogs (3d, 4d, and 5d), among each series, displayed the highest affinity for the adenosine A1 receptor with Ki values in the nanomolar range. This ethyl-substitution pattern was previously unknown to enhance adenosine A1 receptor binding affinity. The 1,3,7-triethyl-substituted analogs (3d, 4d, and 5d) behaved as adenosine A1 receptor antagonists in GTP shift assays performed with either rat cortical or whole brain membranes expressing adenosine A1 receptors. Further, in vivo evaluation of 3d showed reversal of adenosine A1 receptor agonist-induced hypolocomotion. In conclusion, the most potent evaluated compound, 8-(3-phenylpropyl)-1,3,7-triethylxanthine (3d), showed both in vitro and in vivo activity, and therefore represent a novel adenosine A1 receptor antagonist that may have potential as a drug candidate for dementia disorders.

The adenosine A2A antagonistic properties of selected C8-substituted xanthines

The adenosine A2A receptor is considered to be an important target for the development of new therapies for Parkinson's disease. Several antagonists of the A2A receptor have entered clinical trials for this purpose and many research

Inhibition of monoamine oxidase by 8-phenoxymethylcaffeine derivatives

A recent study has reported that a series of 8-benzyloxycaffeines are potent and reversible inhibitors of both human monoamine oxidase (MAO) isoforms, MAO-A and -B. In an attempt to discover additional caffeine derivatives with potent MAO inhibitory activities, and to contribute to the known structure-activity relationships of MAO inhibition by caffeine derived compounds, the present study investigates the MAO inhibitory potencies of series of 8-phenoxymethylcaffeine and 8-[(phenylsulfanyl)methyl]caffeine derivatives. The results document that the 8-phenoxymethylcaffeine derivatives act as potent reversible inhibitors of MAO-B, with IC50 values ranging from 0.148 to 5.78 μM. In contrast, the 8-[(phenylsulfanyl)methyl]caffeine derivatives were found to be weak inhibitors of MAO-B, with IC50 values ranging from 4.05 to 124 μM. Neither the 8-phenoxymethylcaffeine nor the 8-[(phenylsulfanyl)methyl]caffeine derivatives exhibited high binding affinities for MAO-A. While less potent than the 8-benzyloxycaffeines as MAO-B inhibitors, this study concludes that 8-phenoxymethylcaffeines may act as useful leads for the design of MAO-B selective inhibitors. Such compounds may find application in the therapy of neurodegenerative disorders such as Parkinson's disease. Using molecular docking experiments, this study also proposes possible binding orientations of selected caffeine derivatives in the active sites of MAO-A and -B.

Synthesis and in vitro bronchospasmolytic activity of 8-aryl, heteroaryl or arylalkyl theophyllines

Twenty-four 8-aryl- or 8-heteroaryl-substituted theophyllines have been synthesized.The substituents are aromatic rings and heterocycles likely to induce an antiallergic effect or a spasmolytic activity.In vitro evaluation of the bronchospasm caused by ac