8-(3-Chlorostyryl)caffeine - CAS 147700-11-6
Catalog number: 147700-11-6
Category: Inhibitor
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Molecular Formula:
C16H15ClN4O2
Molecular Weight:
330.77
COA:
Inquire
Targets:
Adenosine A2a
Description:
Selective A2A antagonist. Also MAO-B inhibitor
Brife Description:
Selective A2A antagonist. Also MAO-B inhibitor
Appearance:
Pale yellow solid
Synonyms:
(E)-8-[2-(3-Chlorophenyl)ethenyl]-3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione; CSC
Solubility:
Soluble to 25 mM in DMSO
Storage:
Store at -20°C
MSDS:
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Quality Standard:
In-house
Quantity:
Grams-Kilos
Boiling Point:
292.1 °C
Melting Point:
559.4 °C at 760 mmHg
InChIKey:
YMUNFKYGBSLPLQ-ONYUMSKCSA-N
InChI:
1S/2C16H15ClN4O2/c2*1-19-12(8-7-10-5-4-6-11(17)9-10)18-14-13(19)15(22)21(3)16(23)20(14)2/h2*4-9H,1-3H3/b2*8-7+
Canonical SMILES:
CN1C(=NC2=C1C(=O)N(C(=O)N2C)C)C=CC3=CC(=CC=C3)Cl.CN1C(=NC2=C1C(=O)N(C(=O)N2C)C)C=CC3=CC(=CC=C3)Cl
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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CAS 147700-11-6 8-(3-Chlorostyryl)caffeine

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