- Synthesis and molecular modeling of 1H-pyrrolopyrimidine-2,4-dione derivatives as ligands for the α1-adrenoceptors
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Three different series of 1H-pyrrolopyrimidine-2,4-dione derivatives were designed and synthesized as ligands for the α1-adrenergic receptors (α1-ARs). A microwave-assisted protocol was developed in order to improve purity and yields
- Pittalà, Valeria,Siracusa, Maria A.,Modica, Maria N.,Salerno, Loredana,Pedretti, Alessandro,Vistoli, Giulio,Cagnotto, Alfredo,Mennini, Tiziana,Romeo, Giuseppe
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experimental part
p. 5260 - 5276
(2011/10/02)
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- An efficient large-scale synthesis of alkyl 5-hydroxy-pyridin- and pyrimidin-2-yl acetate
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The synthesis of methyl 2-(5-hydroxy-3-methoxypyridin-2-yl)acetate and alkyl 2-(5-hydroxypyrimidin-2-yl)acetate is described. Methodology for an efficient access to 5-hydroxy-pyridin- and pyrimidin-2-yl acetate cores has been developed. Based on the difference in halogen reactivity, 5-bromo-2-chloropyridine and its pyrimidine analogue were functionalized judiciously by SNAr and palladium-catalyzed reactions. The outlined strategy provides a high-yielding route suitable for large-scale synthesis of these compounds as well as paves the way for a potential rapid access to other heterocyclic analogues.
- Morgentin, Rémy,Jung, Frédéric,Lamorlette, Maryannick,Maudet, Micka?l,Ménard, Morgan,Plé, Patrick,Pasquet, Georges,Renaud, Fabrice
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experimental part
p. 757 - 764
(2009/04/07)
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- 3-Arylpiperazinylethyl-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione derivatives as novel, high-affinity and selective α1- adrenoceptor ligands
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The discovery of a new series of selective and high-affinity α1-adrenoceptor (α1-AR) ligands, characterized by a 1H-pyrrolo[2,3-d]-pyrimidine-2,4(3H,7H)-dione system, is described in this paper. Some synthesized compounds, including 20, 22, and 30, displayed affinity in the nanomolar range for α1-ARs and substantial selectivity with respect to 5-HT1A and dopaminergic D1 and D 2 receptors. Functional assays, performed on selected derivatives, showed antagonistic properties.
- Pittala, Valeria,Romeo, Giuseppe,Salerno, Loredana,Siracusa, Maria Angela,Modica, Maria,Materia, Luisa,Mereghetti, Ilario,Cagnotto, Alfredo,Mennini, Tiziana,Marucci, Gabriella,Angeli, Piero,Russo, Filippo
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p. 150 - 153
(2007/10/03)
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