8-(3-Chlorostyryl)caffeine

Names

[ Name ]:
8-(3-Chlorostyryl)caffeine

[Synonym ]:
(E)-8-(3-chlorostyryl)-1,3,7-trimethylxanthine
(E)-1,3-Diethyl-8-(2-(3,4-dimethoxyphenyl)ethenyl)-3,7-dihydro-1H-purine-2,6-dione
(E)-8-[2-(3,4-dimethoxyphenyl)vinyl]-1,3-diethyl-3,7-dihydropurine-2,6-dione
1H-Purine-2,6-dione,3,7-dihydro-1,3-diethyl-8-(2-(3,4-dimethoxyphenyl)ethenyl)-,(E)
8-(3-Chlorostyryl)caffeine
(E)-8-(3,4-dimethoxystyryl)-1,3-diethyl-1H-purine-2,6(3H,7H)-dione
(E)-1,3,7-trimethyl-8-(3-chlorostyryl)xanthine
(E)-8-(3,4-Dimethoxystyryl)-1,3-diethylxanthine
8-[(E)-2-(3-Chlorophenyl)vinyl]-1,3,7-trimethyl-3,7-dihydro-1H-pu rine-2,6-dione
8-(3-chloro-(E)-styryl)caffeine
(E)-8-(3-chlorostyryl)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione

Biological Activity

[Description]:

(E)-8-(3-Chlorostyryl)caffeine is a selective adenosine A2A receptor antagonist. (E)-8-(3-Chlorostyryl)caffeine inhibits monoamine oxidase B (MAO-B) with a Ki value of 70 nM by a pathway that is independent of its actions on the A2A receptor. (E)-8-(3-Chlorostyryl)caffeine has the potential for Parkinson's disease research[1].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> Monoamine Oxidase

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> Adenosine Receptor

[Target]

A2AR

MAO-B:70 nM (Ki)

[References]

[1]. Nevil Vlok, et al. Inhibition of monoamine oxidase B by analogues of the adenosine A2A receptor antagonist (E)-8-(3-chlorostyryl)caffeine (CSC). Bioorg Med Chem. 2006 May 15;14(10):3512-21.

Chemical & Physical Properties

[ Density]:
1.36g/cm3

[ Boiling Point ]:
559.4ºC at 760 mmHg

[ Molecular Formula ]:
C₁₆H₁₅ClN₄O₂

[ Molecular Weight ]:
330.76900

[ Flash Point ]:
292.1ºC

[ Exact Mass ]:
330.08800

[ PSA ]:
61.82000

[ LogP ]:
1.79450

[ Vapour Pressure ]:
1.52E-12mmHg at 25°C

[ Index of Refraction ]:
1.656

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

Articles

Decreased extracellular adenosine levels lead to loss of hypoxia-induced neuroprotection after repeated episodes of exposure to hypoxia.

PLoS ONE 8(2) , e57065, (2013)

Achieving a prolonged neuroprotective state following transient ischemic attacks (TIAs) is likely to effectively reduce the brain damage and neurological dysfunction associated with recurrent stroke. ...

Effect of adenosine A(2A) receptor antagonists and L-DOPA on hydroxyl radical, glutamate and dopamine in the striatum of 6-OHDA-treated rats.

Neurotox. Res. 21 , 222-30, (2011)

A(2A) adenosine receptor antagonists have been proposed as a new therapy of PD. Since oxidative stress plays an important role in the pathogenesis of PD, we studied the effect of the selective A(2A) a...

Vinegar intake enhances flow-mediated vasodilatation via upregulation of endothelial nitric oxide synthase activity.

Biosci. Biotechnol. Biochem. 74 , 1055-61, (2010)

This study examined the effect of acetate on endothelial nitric oxide synthase (eNOS) in human umbilical vein endothelial cells (HUVECs) by immunoblotting assay and the ability of acetic acid to upreg...