155270-98-7

Basic information

• Product Name: 8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione
• Synonyms: 8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione;(E)-8-[2-(3,4-diMethoxyphenyl)vinyl)-1,3-diethyl-3,7-dihydropurine-2,6-dione;(E)-8-(3,4-diMethoxystyryl)-1,3-diethyl-1H-purine-2,6(3H,7H)-dione;(E)-8-(3,4-dimethoxystyryl)-1,3-diethyl-3,7-dihydro-1H-purin-2,6-dione;(E)-8-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-3,7-dihydro-1H-purine-2,6-dione;8-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-7H-purine-2,6-dione
• CAS NO: 155270-98-7
• Molecular Formula: C₁₉H₂₂N₄O₄
• Molecular Weight: 370.4
• Mol File: 155270-98-7.mol

Chemical Properties

• Melting Point: 267 °C(Solv: N,N-dimethylformamide (68-12-2))
• Boiling Point: 612.9°Cat760mmHg
• Flash Point: 324.5°C
• Appearance: /
• Density: 1.280
• Vapor Pressure: 5.85E-15mmHg at 25°C
• Refractive Index: 1.631
• PKA: 7.98±0.70(Predicted)
• CAS DataBase Reference: 8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione(155270-98-7)
• EPA Substance Registry System: 8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione(155270-98-7)

Safety Data

• Hazardous Substances Data: 155270-98-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione is utilized as a lead compound for the discovery and development of new drugs. Its unique structure and potential pharmacological properties make it a valuable candidate for further study and evaluation in the fields of chemistry and pharmacology.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione is employed as a starting point for the design and synthesis of new therapeutic agents. Its purine analog nature allows for the exploration of its interactions with biological targets and the optimization of its pharmacological profile.
Used in Drug Discovery:
8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione is used as a tool in drug discovery to identify potential therapeutic agents with novel mechanisms of action. Its unique chemical features may enable the development of drugs that target specific biological pathways or receptors, offering new treatment options for various diseases and conditions.
Used in Biochemical Research:
In biochemical research, 8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione serves as a probe to investigate the role of purines in cellular processes and signaling pathways. Its structural similarity to natural purines allows researchers to explore its interactions with enzymes, receptors, and other biomolecules, providing insights into the fundamental mechanisms of purine-mediated biological activities.
Used in Drug Synthesis:
8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione is employed as a key intermediate in the synthesis of new drugs with therapeutic potential. Its unique chemical structure can be modified and optimized to generate a diverse range of purine-based compounds with improved pharmacological properties and selectivity for specific targets.
Used in Drug Design:
In the field of drug design, 8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione is utilized as a template for the development of new therapeutic agents. Its purine analog nature provides a foundation for the rational design of drugs with tailored pharmacological profiles, targeting specific diseases and conditions.
Used in Drug Screening:
8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione is used as a compound in drug screening assays to identify its potential therapeutic effects and evaluate its safety and efficacy. Its unique chemical features make it a valuable candidate for high-throughput screening campaigns aimed at discovering new drugs with novel mechanisms of action.
Used in Preclinical Studies:
In preclinical studies, 8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione is employed to assess its pharmacological properties, safety, and efficacy in animal models. These studies provide valuable information on its potential as a therapeutic agent and inform the progression of the compound towards clinical development.

InChI:InChI=1/C19H22N4O4/c1-5-22-17-16(18(24)23(6-2)19(22)25)20-15(21-17)10-8-12-7-9-13(26-3)14(11-12)27-4/h7-11H,5-6H2,1-4H3,(H,20,21)/b10-8+

Upstream product

• 52998-22-8 5,6-diamino-1,3-diethyluracil 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 89073-60-9 6-amino-1,3-diethyl-5-nitroso-1H,3H-pyrimidine-2,4-dione 
• 58045-88-8 3,4-dimethoxycinnamaldehyde 
• 634-95-7 N,N-diethylurea 
• 39856-08-1 (E)-3,4-dimethoxycinnamic chloride 
• 41740-15-2 6-amino-1,3-diethyluracil 
• 187393-68-6 (E)-N-(6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(3,4-dimethoxyphenyl)propenamide 

Downstream Products

• 155270-99-8 istradefylline 
• 606080-73-3 (Z)-1,3-diethyl-8-(3,4-dimethoxystyryl)-7-methylxanthine 

Relevant articles and documents

A Iraq curved theophylline preparation of intermediate

The invention relates to a preparation method of an istradefylline intermediate, which comprises the following steps: by using (E)-1,3-diethyl-6-amino-5-(3,4-dimethoxyphenylacryloyl)amino-uracil (YQ-1) as a raw material and 1,4-dioxane as a solvent, heating under the alkaline condition of a NaOH water solution to perform condensation and cyclization to generate (E)-8-[2-(3,4-dimethoxyphenyl)vinyl]-1,3-diethyl-3,7-dihydro-1H-purinyl-2,6-dione (YQ-2), and carrying out rotary evaporation, acid regulation and vacuum filtration to obtain a YQ-2 crude product; and by using toluene as a solvent, recrystallizing the YQ-2 crude product to obtain the YQ-2 refined product. The method has the advantages of simple route, accessible raw materials and mild conditions, and is convenient to operate; the total yield is greater than 85%, and the purity is up to higher than 97%; and thus, the method is suitable for scale-up production.

Istradefylline raw material drug and preparation method thereof

The invention relates to an istradefylline raw material drug and a preparation method thereof. Specifically, the invention relates to an istradefylline raw material drug. A compound shown in formula III is not higher than 0.5% and is a medicine preparation consisting of the istradefylline raw material drug and a pharmacologically acceptable carrier and/ or diluent. The raw material drug and the preparation thereof have better safety, effectiveness and stability. The formula III is shown in the description.

Improved synthesis technology of istradefylline

The invention provides an improved synthesis technology of istradefylline. According to the technology, istradefylline is prepared from 1,3-diethyl-6-amino-5-nitrosouracil (SM-III) as a starting material through four steps.

Novel adenosine A2A receptor ligands: A synthetic, functional and computational investigation of selected literature adenosine A2A receptor antagonists for extending into extracellular space

Growing evidence has suggested a role in targeting the adenosine A 2A receptor for the treatment of Parkinson's disease. The literature compounds KW 6002 (2) and ZM 241385 (5) were used as a starting point from which a series of novel ligands targeting the adenosine A2A receptor were synthesized and tested in a recombinant human adenosine A2A receptor functional assay. In order to further explore these molecules, we investigated the biological effects of assorted linkers attached to different positions on selected adenosine A2A receptor antagonists, and assessed their potential binding modes using molecular docking studies. The results suggest that linking from the phenolic oxygen of selected adenosine A2A receptor antagonists is relatively well tolerated due to the extension towards extracellular space, and leads to the potential of attaching further functionality from this position.

An efficient route to xanthine based A2A adenosine receptor antagonists and functional derivatives

A one-pot route to 8-substituted xanthines has been developed from 5,6-diaminouracils and carboxaldehydes. Yields are good and the process applicable to a range of substrates including a family of A2A adenosine receptor antagonists. A new route to the KW-6002 family of antagonists is presented including a pro-drug variant, and application to related image contrast agents developed.

Multigram-Scale Syntheses, Stability, and Photoreactions of A2A Adenosine Receptor Antagonists with 8-Styrylxanthine Structure: Potential Drugs for Parkinson's Disease

The improved multigram-scale syntheses of the important 8-styrylxanthine A2A adenosine receptor antagonist MSX-2 (8), its water-soluble prodrug MXS-3 (9), and KW-6002 (16) are described. N-Alkylation reactions at different positions of uracil derivatives were optimized. Two different methods for xanthine formation from 6-amino-5-cinnainoylaminouracil precursors were investigated, (a) the elimination of water by alkaline catalysis and (b) hexamethyldisilazane as a condensing agent; the latter was found to be superior. The photosensitivity of 8-styrylxanthines was studied. The (E)-configurated stryrylxanthine MSX-2 (8) isomerized in diluted solution, and the resulting (Z)-isomer (10a) was isolated and characterized. Furthermore, we describe for the first time that solid 8-styrylxanthines can dimerize upon exposition to daylight or irradiation with UV light. The resulting cyclobutane derivatives with head-to-tail (syn) configuration exhibited a considerably lower A 2A adenosine receptor affinity than their parent compounds. The dimerization product of MSX-2 was a moderately potent nonselective A 1 and A2A antagonist (Ki(Ai) = 273 nM, Ki(A2A) = 175 nM) while the dimer of the related compound KW-6002 was inactive at A1 and only weakly active at A 2A adenosine receptors (Ki = 1.57 μM). The light sensitivity of 8-styrylxanthine derivatives, not only in solution, but also in the solid state, has to be considered when using those compounds as pharmacological tools or drugs.

Inhibition of monoamine oxidase B by selective adenosine A2A receptor antagonists

Adenosine receptor antagonists that are selective for the A2A receptor subtype (A2A antagonists) are under investigation as possible therapeutic agents for the symptomatic treatment of the motor deficits associated with Parkinson's disease (PD). Results of recent studies in the MPTP mouse model of PD suggest that A2A antagonists may possess neuroprotective properties. Since monoamine oxidase B (MAO-B) inhibitors also enhance motor function and reduce MPTP neurotoxicity, we have examined the MAO-B inhibiting properties of several A2A antagonists and structurally related compounds in an effort to determine if inhibition of MAO-B may contribute to the observed neuroprotection. The results of these studies have established that all of the (E)-8-styrylxanthinyl derived A2A antagonists examined display significant MAO-B inhibitory properties in vitro with Ki values in the low μM to nM range. Included in this series is (E)-1,3-diethyl-8-(3,4-dimethoxystyryl)-7-methylxanthine (KW-6002), a potent A2A antagonist and neuroprotective agent that is in clinical trials. The results of these studies suggest that MAO-B inhibition may contribute to the neuroprotective potential of A2A receptor antagonists such as KW-6002 and open the possibility of designing dual targeting drugs that may have enhanced therapeutic potential in the treatment of PD.

Adenosine A(2A) antagonists with potent anti-cataleptic activity

Structure-activity relationships of 8-styrylxanthines for in vivo adenosine A(2A) antagonism were explored. Diethyl substitution both at the 1- and S-position was found to dramatically potentiate the anti-cataleptic activity.

Antidepressants

The present invention relates to an antidepressant containing as an active ingredient a xanthine derivative or a pharmaceutically acceptable salt thereof, the xanthine derivative being represented by Formula (I) : STR1 in which R1, R2, and R3 represent independently hydrogen, lower alkyl, lower alkenyl; R4 represents cycloalkyl, --(CH2)n --R5 (in which R5 represents substituted or unsubstituted aryl or a substituted or unsubstituted heterocyclic group; and n is an integer of 0 to 4), or STR2 (in which Y1 and Y2 represent independently hydrogen, halogen or lower alkyl; and Z represents substituted or unsubstituted aryl, STR3 (in which R6 represents hydrogen, hydroxy, lower alkyl, lower alkoxy, halogen, nitro, or amino; and m represents an integer of 1 to 3), or a substituted or unsubstituted heterocyclic group); and X1 and X2 represent independently O or S.

Therapeutic agent for Parkinson's disease

Agents for the treatment of Parkinson''s disease contain, as an active ingredient, a xanthine derivative or a pharmaceutically acceptable salt thereof. The xanthine derivative is represented by the formula: STR1 in which R 1, R 2 are R 3 are independently hydrogen, lower alkyl, lower alkenyl, or lower alkynyl; and R 4 represents cycloalkyl, --(CH 2) n --R 5 (in which R 5 represents substituted or unsubstituted aryl or a substituted or unsubstituted heterocyclic group; and n is an integer of 0 to 4), or STR2 in which Y 1 and Y 2 represent independently hydrogen, halogen, or lower alkyl; and Z represents substituted or unsubstituted aryl, STR3 in which R 6 represents hydrogen, hydroxy, lower alkyl, lower alkoxy, halogen, nitro, or amino; and m represents an integer of 1 to 4, or a substituted or unsubstituted heterocyclic group; and X 1 and X 2 represent independently O or S.