8-(3-Chlorostyryl)caffeine - CAS 147700-11-6
Catalog number: 147700-11-6
Category: Inhibitor
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Molecular Formula:
Molecular Weight:
Adenosine A2a
Selective A2A antagonist. Also MAO-B inhibitor
Brife Description:
Selective A2A antagonist. Also MAO-B inhibitor
Pale yellow solid
(E)-8-[2-(3-Chlorophenyl)ethenyl]-3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione; CSC
Soluble to 25 mM in DMSO
Store at -20°C
Quality Standard:
Boiling Point:
292.1 °C
Melting Point:
559.4 °C at 760 mmHg
Canonical SMILES:
1.Synthesis of (E)-8-(3-chlorostyryl)caffeine analogues leading to 9-deazaxanthine derivatives as dual A(2A) antagonists/MAO-B inhibitors.
Rivara S1, Piersanti G, Bartoccini F, Diamantini G, Pala D, Riccioni T, Stasi MA, Cabri W, Borsini F, Mor M, Tarzia G, Minetti P. J Med Chem. 2013 Feb 14;56(3):1247-61. doi: 10.1021/jm301686s. Epub 2013 Jan 16.
A systematic modification of the caffeinyl core and substituents of the reference compound (E)-8-(3-chlorostyryl)caffeine led to the 9-deazaxanthine derivative (E)-6-(4-chlorostyryl)-1,3,5,-trimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4-(3H,5H)-dione (17f), which acts as a dual human A(2a) antagonist/MAO-B inhibitor (K(i)(A(2A)) = 260 nM; IC(50)(MAO-B) = 200 nM; IC(50)(MAO-A) = 10 μM) and dose dependently counteracts haloperidol-induced catalepsy in mice from 30 mg/kg by the oral route. The compound is the best balanced A(2A) antagonist/MAO-B inhibitor reported to date, and it could be considered as a new lead in the field of anti-Parkinson's agents. A number of analogues of 17f were synthesized and qualitative SARs are discussed. Two analogues of 17f, namely 18b and 19a, inhibit MAO-B with IC(50) of 68 and 48 nM, respectively, being 5-7-fold more potent than the prototypical MAO-B inhibitor deprenyl (IC(50) = 334 nM).
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