8-(3-Chlorostyryl)caffeine

Base Information

• Chemical Name: 8-(3-Chlorostyryl)caffeine
• CAS No.: 147700-11-6
• Molecular Formula: C16H15ClN4O2
• Molecular Weight: 330.77
• DSSTox Substance ID: DTXSID60872447
• Nikkaji Number: J551.288C,J622.531D
• Wikidata: Q27076920
• Pharos Ligand ID: 6USCJWBQL5KV
• Metabolomics Workbench ID: 58553
• ChEMBL ID: CHEMBL26138
• Mol file: 147700-11-6.mol

Synonyms:1,3,7-trimethyl-8-(3-chlorostyryl)xanthine;8-(3-chlorostyryl)caffeine;8-CSC

Chemical Property of 8-(3-Chlorostyryl)caffeine

Chemical Property:

• Vapor Pressure: 1.52E-12mmHg at 25°C
• Melting Point: 559.4 °C at 760 mmHg
• Refractive Index: 1.656
• Boiling Point: 292.1 °C
• PKA: 0.12±0.70(Predicted)
• Flash Point: 292.1°C
• PSA: 61.82000
• Density: 1.36 g/cm³
• LogP: 1.79450
• Storage Temp.: −20°C
• Solubility.: DMSO: >5mg/mL
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 330.0883534
• Heavy Atom Count: 23
• Complexity: 526

Purity/Quality:

99% ^*data from raw suppliers

8-(3-Chlorostyryl)caffeine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1C(=NC2=C1C(=O)N(C(=O)N2C)C)C=CC3=CC(=CC=C3)Cl
• Isomeric SMILES: CN1C(=NC2=C1C(=O)N(C(=O)N2C)C)/C=C/C3=CC(=CC=C3)Cl
• 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.

Technology Process of 8-(3-Chlorostyryl)caffeine

There total 6 articles about 8-(3-Chlorostyryl)caffeine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (58-08-2,138455-22-8,95789-13-2) + 3-Chlorostyrene (2039-85-2,26100-04-9) → 8-(3-chlorostyryl)caffeine (147700-11-6,148589-13-3)

Guidance literature:

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione; With pyridine; palladium diacetate; copper(II) acetate monohydrate; copper(l) chloride; In N,N-dimethyl acetamide; at 20 ℃; for 0.0833333h; Inert atmosphere;

3-Chlorostyrene; In N,N-dimethyl acetamide; at 120 ℃; for 20h; Inert atmosphere;

DOI:10.1039/c2cc17557f

Reference yield:

8-[(E)-2-(3-Chloro-phenyl)-vinyl]-1,3-dimethyl-3,7-dihydro-purine-2,6-dione (226563-82-2) + methyl iodide (74-88-4) → 8-(3-chlorostyryl)caffeine (147700-11-6,148589-13-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 0.5h; Yield given;

DOI:10.1021/jm00062a005

Reference yield:

4,5-Diamino-1,3-dimethyluracil (5440-00-6) → 8-(3-chlorostyryl)caffeine (147700-11-6,148589-13-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; hydrochloric acid / dioxane; H₂O / 2 h / pH 5

1.2: sodium hydroxide / dioxane; H₂O / 0.75 h / Heating

2.1: potassium carbonate / dimethylformamide / 1 h / 50 °C

With hydrogenchloride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.01.011

upstream raw materials:

8-[(E)-2-(3-Chloro-phenyl)-vinyl]-1,3-dimethyl-3,7-dihydro-purine-2,6-dione

methyl iodide

4,5-Diamino-1,3-dimethyluracil

m-Chlorocinnamic acid

Downstream raw materials:

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

Refernces

• 1、 Huang, Yumin,Song, Feijie,Wang, Zhen,Xi, Peihua,Wu, Ningjie,Wang, Zhigang,Lan, Jingbo,You, Jingsong. "Dehydrogenative Heck coupling of biologically relevant N-heteroarenes with alkenes: Discovery of fluorescent core frameworks". supporting information; experimental part. p. 2864 - 2866. Retrieved 2012/04/17.
• 2、 Petzer, Jacobus P.,Steyn, Salome,Castagnoli, Kay P.,Chen, Jiang-Fan,Schwarzschild, Michael A.,Van Der Schyf, Cornelis J.,Castagnoli, Neal. "Inhibition of monoamine oxidase B by selective adenosine A2A receptor antagonists". . p. 1299 - 1310. Retrieved 2007/10/03.