147700-11-6

Basic information

• Product Name: 8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO
• Synonyms: 8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO;1,3,7-Trimethyl-8-(3-chlorostyryl)xanthine, CSC;1H-Purine-2,6-dione,8-[(1E)-2-(3-chlorophenyl)ethenyl]-3,7-dihydro-1,3,7-triMethyl-;8-[2-(3-Chloro-phenyl)-vinyl]-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione
• CAS NO: 147700-11-6
• Molecular Formula: C₁₆H₁₅ClN₄O₂
• Molecular Weight: 330.773
• Mol File: 147700-11-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 205 °C
• Boiling Point: 292.1 °C
• Flash Point: 292.1°C
• Appearance: white/
• Density: 1.36 g/cm³
• Vapor Pressure: 1.52E-12mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: −20°C
• Solubility: DMSO: >5mg/mL
• PKA: 0.12±0.70(Predicted)
• CAS DataBase Reference: 8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO(CAS DataBase Reference)
• NIST Chemistry Reference: 8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO(147700-11-6)
• EPA Substance Registry System: 8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO(147700-11-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 147700-11-6(Hazardous Substances Data)

Usage

Description

8-(3-Chlorostyryl)caffeine (CSC) is an adenosine A2 receptor antagonist (Ki = 54 nM). It is selective for adenosine A2 over A1 receptors (Ki = 28 μM). CSC reverses locomotor depression induced by the adenosine A2A agonist APEC in mice (ED50 = 16 μg/kg, i.p.). It increases locomotion in mice when administered at a dose of 5 mg/kg. CSC (5 mg/kg) reverses the shortening of the rotational motor response and increases in striatal adenosine A2 receptor levels induced by L-DOPA in a rat model of Parkinson’s disease induced by 6-OHDA . It also inhibits monoamine oxidase B (MAO-B; Ki = 100 nM) and reduces MAO-B activity in brain mitochondrial preparations from wild-type and A2A-/- mice.

Uses

8-(3-Chlorostyryl)caffeine is a selective Adenosine A2A-R and MAO-B inhibitor.

Definition

ChEBI: Caffeine substituted at its 8-position by an (E)-3-chlorostyryl group.

InChI:InChI=1/C16H15ClN4O2/c1-19-12(8-7-10-5-4-6-11(17)9-10)18-14-13(19)15(22)21(3)16(23)20(14)2/h4-9H,1-3H3/b8-7+

Upstream product

• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 2039-85-2 3-Chlorostyrene 
• 1026497-99-3 (E)-N-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-(3-chloro-phenyl)-acrylamide 
• 1866-38-2 m-Chlorocinnamic acid 
• 5440-00-6 4,5-Diamino-1,3-dimethyluracil 
• 226563-82-2 8-[(E)-2-(3-Chloro-phenyl)-vinyl]-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 
• 74-88-4 methyl iodide 

Downstream Products

• 148589-13-3 8-[(Z)-2-(3-Chloro-phenyl)-vinyl]-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione 

Relevant articles and documents

(E)-8-(3-Chlorostyryl)-1,3,7-trimethylxanthine, a caffeine derivative acting both as antagonist of adenosine A2A receptors and as inhibitor of MAO-B

In the crystal structure of (E)-8-(3-chlorostyryl)-1,3,7- trimethylxanthine (CSC) [systematic name: (E)-8-(3-chlorostyryl)-1,3,7-trimethyl-3,7-dihydro-1H- purine-2,6-dione], C16H15ClN4O2, the xanthine ring and the lateral styryl chain are coplanar. The crystal packing involves mainly parallel stacking of these planar molecules. The electrostatic potential calculated on the crystal structure conformation confirms the pharmacophore elements associated with MAO-B inhibition.

Inhibition of monoamine oxidase B by analogues of the adenosine A2A receptor antagonist (E)-8-(3-chlorostyryl)caffeine (CSC)

The adenosine A2A receptor has emerged as a possible target for the treatment of Parkinson's disease (PD). Evidence suggests that antagonism of the A2A receptor not only improves the symptoms of the disease but may also protect again

Structure-activity relationships of 8-styrylxanthines as A2-selective adenosine antagonists

A series of substituted 8-styryl derivatives of 1,3,7-alkylxanthines was synthesized as potential A2-selective adenosine receptor antagonists, and the potency at rat brain A1- and A2-receptors was studied in radioligand bi